- Two coumarin-based turn-on fluorescent probes based on for hypochlorous acid detection and imaging in living cells
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This work, two turn-on fluorescent probes (3-acetyl-2H-chromen-2-one (ACO) & (1E)-1-(1-(2-oxo-2H-chromen-3-yl)ethylidene)thiosemicarbazide (CETC)) based on coumarin have been designed and synthesized, which could selectively and sensitively recognize ClO? with fast response time. ACO & CETC were almost non fluorescent possibly due to both the lacton form of coumarin and unbridged C[dbnd]N bonds which can undergo a nonradiative decay process in the excited state. Upon the addition of ClO?, ACO & CETC were oxidized to ring - opened by cleavage the C–O and C[dbnd]N and the fluorescence intensity were increased considerably. Fluorescence titration experiments showed that the detection limit ACO & CETC is as low as 22 nm and 51 nm respectively. In particular, some relevant reactive species, including [rad]OH, 1O2, H2O2, KO2, some anions and cations cannot be interference with the test. In live cell experiments, ACO & CETC were successfully applied to image exogenous ClO? in HepG2 cells. Therefore, ACO & CETC not only could image ClO? in living cells but also proved that C–O and C[dbnd]N can be cleavage by ClO?.
- Wang, Qingming,Jin, Lei,Wang, Wenling,Dai, Lihui,Tan, Xiaoxue,Zhao, Cong
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- Synthesis of some substituted pyrimidines derived from 3-acetyl coumarin
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This study targets mainly the synthesis of a number of derivatives of coumarin containing ring pyrimidin-2-one substitutes different aromatic rings, taking advantage of the Biginelli reaction which includes the reaction of 3-acetyl coumarin with suitable
- Al-Radha, Nabeel A.A.,Jaber, Qassim A.H.
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- Unexpected transformations of 3-(bromoacetyl)coumarin provides new evidence for the mechanism of thiol mediated dehalogenation of α-halocarbonyls
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The mechanism for the thiol mediated dehalogenation of α-halogenated carbonyls has remained an unresolved problem, despite its ongoing application in synthetic organic chemistry. Nakamura and co-workers first proposed that net dehalogenation occurs via sequential nucleophilic substitutions, while Israel and co-workers concluded that the rate at which dehalogenation occurred suggested that dehalogenation proceeds in a single concerted step. In this study, we investigated the debromination and nucleophilic substitution of 3-(bromoacetyl)coumarin with a variety of thiophenols, whose electron donating or withdrawing natures resulted in large variations in the degree of nucleophilic substitution and dehalogenation products, respectively. Results from these experiments, in addition to an unexpected formation of thioether containing dibenzo[b,d]pyran-6-ones from a Robinson annulation, has provided new evidence for this disputed mechanism.
- Magwenzi, Faith N.,Khanye, Setshaba D.,Veale, Clinton G.L.
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- Dual-function fluorescent probe with red emission for sensing viscosity and OCl? and its applications in bioimaging
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The microenvironment in biological systems is associated with pathological of organisms. In this work, HBTC, a red-emitting probe with abilities of responding to OCl? and environmental viscosity was designed and synthesized to preliminary apply
- Cui, Yali,Jiang, Yingxia,Sun, Xiaodong,Wang, Ruijie,Yan, Fanyong,Zhang, Yuyang
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- Design, synthesis and computational studies involving Indole-Coumarin hybrids as galectin-1 inhibitors
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In continuation of our quest to develop non-carbohydrate galectin-1 inhibitors, we have designed and synthesized 20 indole-coumarin hybrids linked via chalcone. Compounds 6i and 7e were found to decrease galectin-1 levels significantly in galectin-1 enzyme assay at 20?μM concentration. Binding affinity studies carried out by fluorescence spectroscopy revealed that 6i binds to galectin-1 with a binding constant (Ka) value of 5.4 × 105?M?1 while 7e was found to have a slightly higher affinity than 6i with Ka of 6.6 × 105?M?1. Molecular docking was carried out to ascertain the interaction between ligand and protein. To further gain structural insights into the binding of the compounds, 30?ns molecular dynamic simulations were carried out. The studies revealed that compound 7e was stable within the subsite C of galectin carbohydrate recognition domain while 6i fluctuated throughout the simulation. In addition, 7e maintained continuous interaction with Trp68 and His52, the two key amino acid residues are responsible for recognition of ligands within the active site. Furthermore, 7e displayed H-bond interactions with highly conserved amino acids within galectin-1 CRD, i.e., Arg48, Asn61 and Glu71. Free energy of binding evaluated by MM-GBSA calculations was also in accordance with experimental data. 7e was calculated to have binding energy of ??53.40?kcal/mole while 6i was found to have a value of ??45.63?kcal/mole. Graphical abstract: [Figure not available: see fulltext.]
- Sethi, Aaftaab,Sasikala,Jakkula, Pranay,Gadde, Divya,Sanam, Swetha,Qureshi, Insaf A.,Talla, Venu,Alvala, Mallika
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- Synthesis and antibacterial activity of Zn(II) Schiff base complexes derived from 3-acetyl-2H-chromen-2-one
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Zn(II) Schiff base complexes viz., bis[(E)-3-(1-(p-tolylimino)ethyl)-2H-chromen-2-one]zinc(II), bis[(E)-3-(1-((4-chlorophenyl)- imino)ethyl)-2H-chromen-2-one]zinc(II) and bis[(E)-3-(1-((2-nitrophenyl)imino)-ethyl)-2H-chromen-2-one]zinc(II) derived from 3-
- Hussain, Habib,Gilani, Syeda Rubina,Jabeen, Farkhanda,Ali, Zulfiqar,Rehman, Hajira,Hussain, Imdad
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- A self-assembled π-conjugated system as an anti-proliferative agent in prostate cancer cells and a probe for intra-cellular imaging
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Multifunctional π-conjugated systems derived from renewable resource that self-assemble into supramolecular structures are reported. The aggregation of compounds in different solvents strongly influences their optical properties. These π-conjugated molecules can be used for live cell imaging applications. They also show low cytotoxicity in fibroblasts and suppress proliferation in PC3 prostate cancer cells.
- Lalitha, Krishnamoorthy,Jenifer, Preethi,Prasad, Y. Siva,Muthusamy, Kumarasamy,John, George,Nagarajan, Subbiah
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- Zn2+ specific colorimetric receptor based on coumarin
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The receptor 1 having coumarin and thiazole as electron-deficient and-rich centers respectively acted as a colorimetric receptor selectively for Zn 2+ as its chloride salt in DMSO/aq. DMSO (10:90 v/v) by exhibiting a remarkable bathochromic shifting of 120 nm in its 375 nm UV-visible absorption band. The interaction of receptor 1 with a number of metal ions ranging from s,p to d blocks as their chloride salts indicated the selectivity of the same toward Zn2+. Transmission electron microscopy (TEM) along with spectroscopic studies indicated Zn2+ triggered aggregate formation of the receptor 1 as the key step toward sensing.
- Upadhyay, Kaushal Kumar,Mishra, Rakesh Kumar
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- An approach for continuous-flow processing of reactions that involve the in situ formation of organic products
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A simple adaptation allows batch protocols developed using microwave heating that involve formation of solid organic products to be scaled up using conventionally-heated flow chemistry with minimal or no re-optimization or modification. The product stream is intercepted with a flow of a suitable organic solvent upon exiting the heated zone, this solubilizing the product and allowing it to pass through the back-pressure regulator without aggregation of particulate material.
- Kelly, Christopher B.,Lee, Christopher,Leadbeater, Nicholas E.
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- Strongly fluorescent organogels and self-assembled nanostructures from pyrene coupled coumarin derivatives: Application in cell imaging
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Three different coumarin coupled pyrene derivatives with varying hydrophobic units (alkyl chains) have been synthesised and well characterized using NMR and mass spectral analysis. The gelation behaviour and self-aggregation properties of these compounds were studied relative to the molecular structure and solvent affinity. Among these derivatives, the one which is not having any hydrophobic tail displays efficient gelation in higher alcohols such as decanol and dodecanol. However the other derivatives having saturated and unsaturated hydrophobic tails form weak gel in different solvents. The morphology of gel was investigated by optical microscopy and high resolution transmission electron microscopy (HRTEM). The investigation of absorption and emission spectra of these compounds revealed that the photo-physical properties were significantly influenced by the self-assembly process in different solvents. The concentration dependent emission and 1H NMR studies clearly suggest that the π-π stacking interaction and hydrogen bonding between carbonyl groups of coumarin coupled pyrene with the -OH group of solvent were the driving forces for the process of gelation and self-aggregation. Rheological investigation clearly demonstrates the flow behaviour and reversible nature of organogel under temperature and strain ramp up and ramp down experimental conditions. By getting clue from the self-assembly mechanism in different solvents, we derived nano-flakes from coumarin coupled pyrene derivatives and further explored their potential applications in the field of cell imaging. The size of the self-aggregated particles in the DMSO-water mixture has been identified using HRTEM and a zetasizer. The nanomaterials obtained via the self-assembly process were used for fibroblast and PC3 prostate cancer cell imaging applications. Further investigation reveals that these compounds suppress the proliferation of PC3 cells.
- Lalitha, Krishnamoorthy,Nagarajan, Subbiah
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- Vibrational assignments and electronic structure calculations for 3-acetylcoumarin
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Laser Raman (3500-50 cm-1) and IR (4000-400 cm-1) spectral measurements have been made on the laboratory prepared solid 3-acetylcoumarin. Molecular electronic energy, equilibrium geometrical structure and harmonic vibrational spectra have been computed at the RHF/6-31G(d,p) and B3LYP/6-31G(d,p) levels of theory. A complete vibrational assignment aided by the theoretical harmonic frequency analysis has been proposed. The B3LYP/6-31G(d,p) geometrical parameters, and frequencies of the C{double bond, long}O in the pyrone and acetyl group are in good agreement with experiment. The difference in the frequencies due to the two carbonyl groups, 50 cm-1, which is attributed to the conjugation effect, is accounted for by the B3LYP to be 56 cm-1.
- Ramoji, Anuradha,Yenagi, Jayashree,Tonannavar,Jadhav,Kulkarni
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- Rational design and synthesis of 3-heteroaromatics coumarin molecules with unusual solution and solid dual efficient luminescence
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3-Imidazolyl coumarin molecules were synthesized under solvent-free condition and the optical properties both in solution and the solid state were determined. The compounds showed dual efficient luminescence, which were blue fluorescence with the highest fluorescence quantum yield being more than 0.9 and also exhibited favorable yellow solid-state fluorescence. Additionally, by using density functional theory (DFT) and time-dependent DFT (TD-DFT) calculation, all structures were optimized and the associated optical performances showed similar results as the experimental results.
- Zhou, Zi-chun,Zheng, An-na,Cui, Yan-hong,Lin, Zhang-qi,Niu, Wen-jie,Zhang, Yong-jian,Gao, Jian-rong,Li, Yu-jin
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- Isonicotinoylhydrazide modified 3-acetylcoumarin scaffold as an efficient chemical reversible sensor to detect Al3+ selectively and its application in live cells imaging
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A turn-on photochromic sensor based on coumarin was designed and synthesized for selective and sensitive detection of Aluminium(III) (Al3+) in ethanol (C2H5OH)/water (H2O; 1:1, v/v) with the detection limit of 0.126 μM. The mechanism was proposed to form a kind of 1:1-type complex between probe C1 and Al3+ in which the binding constant was 3.11 × 107 M?1. In addition, the sensor was effectively used for the detection of Al3+ in living HEK293T cells.
- Wang, Wenling,Jin, Lei,Kuang, Yang,Yuan, Zhongzhong,Wang, Qingming
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- Synthesis, Characterization, Optical, Electrochemical and Current-Voltage Characteristics of Coumarin Dyes
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A series of coumarin dyes having common acceptor and pi spacer with different donors were synthesized and characterized by spectroscopic techniques. The TiO2 nanoparticle has been synthesized by sol-gel method and characterized by X-ray diffrac
- Basavarajappa,Nayaka, Y. Arthoba,Yathisha,Manjunatha
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- Synthesis and characterization of some heteroaromatic derivatives of 3-but-2-enoyl-chromen-2-one and their potential as anti-inflammatory agents
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A novel series of chromen-2-ones containing pyrazole, isoxazole, oxazine, and thiazine substitutions have been synthesized by reacting 3-[3-(4-chloro-phenyl)-acryloyl]-chromen-2-one and 3-[3-(3-methoxy-phenyl)- acryloyl]-chromen-2-one with various cyclizing agents such as hydrazine, phenylhydrazine, urea, and thiourea. The structures of all the synthesized compounds were confirmed by the use of IR, 1H-NMR, mass spectroscopy, and elemental analysis data. All the newly synthesized compounds were evaluated for their anti-inflammatory activity at a dose of 100 mg/kg body weight in carrageenan-induced rat paw edema model. The entire series of the compounds exhibited moderate to good anti-inflammatory activity, with the percentage inhibition of edema formation ranging from 39.99 to 63.15 against the reference drug ibuprofen (100 mg/kg) that showed 78.96% inhibition at the third hour. Compounds 3a, 3c, and 3d showed good inhibitory activity, whereas compounds 3b, 3e, 3f, and 3j showed moderate inhibitory activity at the third hour.
- Dixit, Priyanka,Tripathi, Avinash C.,Saraf, Shailendra K.
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- Spectroscopic and biophysical studies on chalcones and schiff bases derived from chromen-2-one and quinoline-2(1h)-one derivatives as antibacterial agents
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A series of chalcone derivatives and arylidene analogues derived from 3-acetyl coumarin were synthesized. The synthesized compounds were elucidated by spectroscopic analysis such as elemental analysis, infrared, 1H & 13C NMR and mass
- Alotaibi, Saad H.
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- One-pot three-component protocol for the synthesis of indolyl-4H-chromene-3-carboxamides as antioxidant and antibacterial agents
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A series of newly synthesized 4-(1H-indol-3-yl)-2-methyl-N-phenyl-4H-chromene-3-carboxamide derivatives were achieved by one-pot reaction between salicylaldehydes, substituted acetoacetanilides, and indoles in methanol catalyzed by 1,4-diazabicyclo [2.2.2]octane (DABCO) (30 mol%) at room temperature. These chromene systems were constructed through Knoevenagel condensation followed by a nucleophilic substitution process. The valuable features of this protocol such as short reaction time, simple operational procedure, broad substrate scope, and high yield of products make it an efficient and promising synthetic strategy. For the first time, various substituted 4H-chromene-3-carboxamide derivatives using DABCO as a catalyst are reported. The synthesized compounds (4a-p) were evaluated in antioxidant and antibacterial studies. The derivatives 4c, 4d, 4k, 4l, and 4p showed good antioxidant activity. Among all the derivatives 4k, 4l, and 4p were found to be active against bacterial strains with MIC values ranging from 9.3 to 18.75 μg mL-1.
- Subbareddy, Chitreddy V.,Sumathi, Shanmugam
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- A Combined Experimental and Computational Investigation on Spectroscopic and Photophysical Properties of a Coumarinyl Chalcone
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Here, we synthesized a new coumarinyl chalcone derivative 3-[3-(3-Methyl-thiophen-2-yl)-acryloyl]-chromen-2-one (MTC) by simple and proficient method. A comprehensive study on the photophysics of a coumarinyl chalcone derivative having pi-conjugated potential chromophore system 3-[3-(3-Methyl-thiophen-2-yl)-acryloyl]-chromen-2-one (MTC) has been carried out spectroscopically. The electronic absorption and emission characteristic of MTC were studied in different protic and aprotic solvents using absorption and steady-state fluorescence techniques. The spectral behavior of this compound is found to be extremely sensitive to the polarity and hydrogen bonding nature of the solvent. The compound shows very strong solvent polarity dependent changes in their photophysical characteristics, namely, remarkable red shift in the emission spectra with increasing solvent polarity, change in Stokes shift, significant reduction in the fluorescence quantum yield; indicating that the fluorescence states of these compounds are of intramolecular charge transfer (ICT) character. The solvent effect on the photophysical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment, fluorescence spectra, and fluorescence quantum yield of the compound has been investigated in detail. The difference between the excited and ground state dipole moments (Δμ) were estimated from solvatochromic methods using Lippert–Mataga and Reichardt’s correlations. The prepared compound was also studied by density functional theory (DFT) and time-dependent density functional theory (TDDFT). The results revealed that it could be easily reproduce by computational means.
- Al-Sehemi, Abdullah G.,Pannipara, Mehboobali,Kalam, Abul,Asiri, Abdullah M.
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- Coumarin-naphthohydrazone ligand with a rare coordination mode to form Mn(II) and Co(II) 1-D coordination polymers: synthesis, characterization, and crystal structure
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The hydrazone (E)-3-hydroxy-N’-(1-(2-oxo-2H-chromen-3-yl)ethylidene)-2-naphthohydrazide (H2L) was synthesized from the reaction of 3-acetylcoumarin and 3-hydroxy-2-naphthoic hydrazide in methanol. Compounds [Mn(H2L)(NO3)2(CH3OH)]?CH3OH (1a), [Mn(HL)(NO3)(CH3OH)]n (1b), [Co(HL)(NO3)(CH3OH)]n (2), and [Cu(HL)(NO3)] (3) were obtained by reaction of an equimolar amount of H2L with nitrate salts of Mn(II), Co(II), or Cu(II) in methanol. The reaction of ligand and Mn(NO3)2·4H2O was also carried out in the presence of sodium azide which led to the 1-D coordination polymer, [Mn(HL)(N3)(CH3OH)]n (4). All of the synthesized compounds were characterized by elemental analyses and spectroscopic methods. Single-crystal X-ray analysis of 1–4 indicated that H2L is neutral (in 1a) or mononegative ligand (in 1b, 2, 3 and 4). In 1b, 2 and 4 the 1-D polymeric chain is found by a rare coordination mode of this kind of hydrazone ligand since the naphtholic oxygen is coordinated to the neighboring metal ions while the NH moiety of hydrazone remains intact, also confirmed by FT-IR spectroscopic studies. The thermal stability of 2 and 4 were also studied from 30–1000?°C.
- Bikas, Rahman,Farzaneh-Bonab, Hossein,Noshiranzadeh, Nader,Aygün, Muhittin,Emami, Marzieh,Lis, Tadeusz
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- Self assembled pseudo double helix architecture and anion sensing behavior of a coumarin based ICT probe
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The X-ray diffraction (XRD) studies of a coumarin based hydrazone (receptor 1) have revealed self assembled pseudo double helix architecture involving closed shell O---O interactions besides other supramolecular interactions. The receptor (1) an intramole
- Upadhyay,Mishra, Rakesh K.,Kumar, Ajit,Zhao, Jianzhang,Prasad, Rajendra
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- Efficient one-pot three-component method for the synthesis of highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives under microwave irradiation
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A simple and concise approach to the synthesis of coumarin-containing highly fluorescent asymmetric/symmetric 3,5-diaryl/heteroaryl-2,6-dicyanoaniline derivatives are reported. The compounds were synthesized through base catalyzed three-component one-pot synthesis reaction of 2-(1-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)ethylidene)malononitrile, aliphatic, aromatic/heteroaromatic aldehydes, and malononitrile in solvent-free reaction medium, catalyzed by piperidine under microwave irradiation method. The reaction gave the novel, highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives in good yields at 300 W, 80 °C in 2 min. This method provides several advantages; such as shorter reaction time, environmental friendliness, simple workup procedure, lower energy consumption and, generally, good yields with high purity. In addition, the synthesized compounds are fluorescently active dyes even in day light, except for compounds including nitro substituent, and show maximum absorption wavelengths (λabs.max) in the visible region in DMSO at room temperature. Thermal properties of all the synthesized compounds were also evaluated with thermal gravimetric analysis for usability as optic dye. Optical and thermal screening studies of the compounds showed that the dyes have excellent photophysical and thermal stability properties.
- Ayd?ner, Burcu,Yal??n, Ergin,Korkmaz, Vildan,Sefero?lu, Zeynel
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- Investigation of the Anticancer Effect of α-Aminophosphonates and Arylidine Derivatives of 3-Acetyl-1-aminoquinolin-2(1H)-one on the DMBA Model of Breast Cancer in Albino Rats with In Silico Prediction of Their Thymidylate Synthase Inhibitory Effect
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Breast cancer is a major cause of death in women worldwide. In this study, 60 female rats were classified into 6 groups; negative control, α-aminophosphonates, arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one, DMBA, DMBA & α-aminophosphonates, and DMBA & aryli-dine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one. New α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one were synthesized and elucidated by different spectroscopic and elemental analysis. Histopathological examination showed marked proliferation of cancer cells in the DMBA group. Treatment with α-aminophosphonates mainly decreased tumor mass. Bcl2 expression increased in DMBA-administered rats and then declined in the treated groups, mostly with α-aminophosphonates. The level of CA15-3 markedly declined in DMBA groups treated with α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one. Gene expression of GST-P, PCNA, PDK, and PIK3CA decreased in the DMBA group treated with α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one, whereas PIK3R1 and BAX increased in the DMBA group treated with α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one. The molecular docking postulated that the investigated compounds can inhibt the Thymidylate synthase TM due to high hydrophobicity charachter.
- Aldhahrani, Adil,Ali, Omar M.,Amer, Hamada H.,Elhenawy, Ahmed,Nassan, Mohamed A.,Swelum, Ayman A.,Zaki, Yasser H.
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- One-pot synthesis of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives
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An efficient synthetic procedure for the preparation of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives was developed. A sequential one-pot, two-step tandem reaction starting from 3-(2-bromoacetyl)-2H-chromen-2-one derivatives synthesized, pyridine, and naphthols in the presence of triethylamine proceeded smoothly in acetonitrile under reflux conditions. In this process, 2-oxo-2H-chromen-3-yl)ethyl)pyridinium bromide derivatives as intermediate produced in situ, followed by Michael addition of naphthoxide anion and intramolecular cylization, resulted the corresponding products in good to high yields. All of the compounds were obtained in high purity without any use of more purification.
- Olyaei, Abolfazl,Feizy, Elaheh,Aghajanzadeh, Atiye
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p. 757 - 765
(2021/01/12)
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- Synthesis and biological screening of thiosemicarbazones of substituted 3-acetylcoumarins having D-glucose moiety
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Thiosemicarbazones 5a-j were synthesized with yields of 45–68% by condensation of 3-acetylcoumarins 3a-j and tetra-O-acetyl-β-D-thiosemicarbazide 4. All obtained thiosemicarbazones were screened for anti-microorganic activities against bacteria (B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeruginosa, K. pneumoniae, S. typhimurium) and fungi (A. niger, C. albicans, S. cerevisiae, and A. flavus). Some compounds had significant inhibitory activity with MICs of 0.78–3.125 μM in comparison with 5a, including 5e,h,i for S. aureus, and 5c,f,i for S. epidermidis (Gram-(+) bacteria), 5c,f,g for E.coli, 5f for K. pneumoniae, 5b,c,g for P. aeruginosa, and 5i for S. typhimurium (Gram-(?) bacteria), 5d,h,i for A. niger, 5i for A. flavus, 5b,d,e,h for C. albicans, and 5i for S. cerevisiae. Compounds exhibited excellent activity against tested microorganism with MIC = 0.78 μM, including 5h,i (against S. aureus), 5h (against C. albicans), and 5i (against S. cerevisiae).
- Ngoc Toan, Vu,Dinh Thanh, Nguyen,Minh Tri, Nguyen,Thi Thu Huong, Nguyen
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supporting information
(2020/11/20)
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- Synthesis and biological evaluation of some coumarin hybrids as selective carbonic anhydrase IX and XII inhibitors
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Two series, coumarin-linked to thiazolidinone via a pyrazole linker (6a-m, Series 1) and coumarin-linked 1,2,3-triazoles (5a-j, Series 2) were synthesized and the synthesized compounds were subjected for evaluation against the four physiologically and pha
- Alvala, Mallika,Angeli, Andrea,Argulwar, Omkar S.,Arifuddin, Mohammed,Soman, Jyothsna,Sridhar Goud, Nerella,Supuran, Claudiu T.,Thacker, Pavitra S.
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- Synthesis, characterization and antimicrobial evaluation of some novel chromenopyridine, pyranochromene and 3-hetarylcoumarin derivatives
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3-Acetylcoumarin was used as a precursor for the synthesis of novel fused heterocyclic compounds as chromeno[3 ,4-c]pyridine, chromeno[4,3-h]pyridine and pyrano[3,4-c]chromene derivatives in addition to the synthesis of 3-hetarylchromene derivatives. The chemical structures of newly synthesized compounds were avowed by means of spectral and analysis data. The novel synthesized compounds were estimated as antibacterial agents against Staphylococcus aureus and Escherichia co/i bacteria.
- Engy, E. Elbialy,Khaled, S. Mohamed
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- Design, synthesis and biological estimation of innovative pyrazoles as anticancer agents targeting CDK2
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CDK2, which exhibits an indispensable role as an organizer of cell growth, is the powerfully studied protein Kinases objective of anticancer suppressors. The present study was dedicated to design (pharmacophore, docking, and binding energy) and to prepare an inspired derivatives of pyrazole and pyrazolo[1,5d]pyrimidine as promising anticancer agents, which can act by targeting CDK2. The promising compounds were selected according to their fit-value and binding energy scores. The anticancer activity against MCF-7 was tested for the prepared compounds and compounds 2, 3b, and 7b showed expressive activity with IC501.75, 0.89 and 1.32 μM respectively. The CDK2 evaluation was carried out to estimate the efficiency of the prepared compounds as promising inhibitors. The results revealed that compound 3b with effective inhibitory activity against tumor growth and with its potent inhibition against the CDK2 enzyme with percent inhibition 86 would be a prospective anticancer agent. The prepared compounds with high biological activity could be used as lead inhibitors for the CDK2 kinase domain.
- Radini, Ibrahim Ali M.,Ibrahim, Diaa A.,Khidre, Rizk E.
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p. 453 - 468
(2019/07/12)
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- Improved one-pot synthetic conditions for synthesis of functionalized fluorescent coumarin-thiophene hybrids: Syntheses, DFT studies, photophysical and thermal properties
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We have synthesized coumarin-thiophene hybrids using stepwise and one-pot methods under MWI and CM conditions, and then report the findings and conclusions: one-pot is better than stepwise in terms of high yields and fastness of getting products, and MWI is better than CM in terms of purity of compounds, better yields, and reaction period. Even though both protocols were found to be efficient, the microwave-assisted irradiation reactions were identified to be better, environmentally friendly, cost-effective, mild, more efficient, less time consuming but with high purity. The two protocols were employed for the synthesis of the target coumarin-thiophene hybrids via the Gewald reaction in stepwise and in one-pot three-component. The dyes 3a-j were prepared in good to excellent yields. Although, we recorded better yields via the stepwise protocol (80–96%), for the synthesis of the target molecules, as compared to the one-pot (82–90%), the stepwise condition is fraught with many changes such as long reaction conditions, extra use of solvents for purification of intermediates, and long reaction durations. Photophysical activities of all the target derivatives were investigated using a combination of UV–vis and fluorescence spectroscopies in different solvents. The umbelliferon-like derivative 3g was further investigated for possible use as a pH sensor via deprotonation (using TBAOH) and reverse protonation (using TFA), and was found to be applicable as pH sensor both in organic medium (DMSO) and partial aqueous binary (DMSO/H2O, v/v, 9:1) medium. Again, the ground and the excited state properties of the umbelliferon-like derivative 3g and its deprotonated form were also studied using the quantum chemical calculations. Finally, the thermal properties of all the target compounds were investigated using TGA in order to test their potency and applicability as optical dyes. All the dyes 3a-j have high thermal stability therefore they can be applicable as optical dyes.
- Yahaya, Issah,Sefero?lu, Nurgül,Sefero?lu, Zeynel
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supporting information
p. 2143 - 2154
(2019/02/28)
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- Continuous flow solvent free organic synthesis involving solids (reactants/products) using a screw reactor
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Here we report for the first-time various organic transformations such as aldol condensation, oxidation, nucleophilic substitutions, protection, acylations and coupling reactions using a mechanochemical approach at a controlled temperature using a single synthesis platform. Almost minimal solvents or solvent-free conditions are used, making it a very efficient and clean synthesis of various products. A jacketed screw reactor when operated at different temperatures (0 °C to 160 °C) and over a range of rotation speeds for changing the residence time (15 s-300 s) helped to achieve maximum conversion. This approach is also extended to the synthesis using substrates having different substitutions, heterocycles and steric hindrance.
- Sharma, Brijesh M.,Atapalkar, Ranjit S.,Kulkarni, Amol A.
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supporting information
p. 5639 - 5646
(2019/10/22)
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- Sensitive colorimetric detection of CN? and AcO? anions in a semi-aqueous environment through a coumarin-naphthalene conjugate azo dye
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In the present study, we described the design and synthesis of an azo auxochrome containing a 2-aminothiazolyl coumarin and naphthalene conjugate as a molecular probe 5. Upon interaction with anions, the probe 5 displayed a naked-eye sensitive colorimetric response towards the detection of cyanide (CN?) and acetate (AcO?) anions in a 50% aqueous-ethanol (EtOH?:?H2O; v/v, 1?:?1) solution. The limits of detection for the cyanide and acetate anions were found to be 0.756 and 0.916 μM, respectively. The mechanism of interaction between the probe and both the anions has been confirmed by different spectroscopic data. The 1H NMR, 13C NMR, FTIR and HRMS data clearly confirmed the deprotonation of probe 5 in the presence of both anions. Moreover, the molecular probe 5 has shown good compatibility for the detection of CN? and AcO? anions on test paper strips.
- Dwivedi, Sushil K.,Razi, Syed S.,Misra, Arvind
-
supporting information
p. 5126 - 5132
(2019/03/29)
-
- Rationally synthesized coumarin based pyrazolines ameliorate carrageenan induced inflammation through COX-2/pro-inflammatory cytokine inhibition
-
In the present work, coumarin based pyrazolines (7a-g) have been synthesized and investigated for their in vitro and in vivo anti-inflammatory potential. Amongst the synthesized compounds, compounds 7a, 7d and 7f exhibited significant in vitro anti-inflammatory activity as compared to the standard etoricoxib. Keeping this in mind, in vivo investigations were carried out via carrageenan induced inflammation and acetic acid induced writhing models in male Wistar rats and compound 7a was found to possess appreciable anti-inflammatory and analgesic potential. The mode of action of compound 7a was also investigated by using substance P as the biomarker, which shows promising results. Further, the selectivity of the most active compound 7a against the cyclooxygenase enzyme was supported by molecular docking studies which reveal that compound 7a has greater binding affinity towards COX-2 over COX-1 and 5-LOX enzymes. In silico ADME analysis of compound 7a confirms the drug-like characteristics and the in vivo acute toxicity study showed the safety of the compound even up to a 2000 mg kg?1 dose. Thus, compound 7a was identified as an effective anti-inflammatory agent, and can be explored for further analgesic/anti-inflammatory drug design and development.
- Chandel, Priyanka,Kumar, Anoop,Singla, Nishu,Kumar, Anshul,Singh, Gagandeep,Gill, Rupinder Kaur
-
supporting information
p. 421 - 430
(2019/03/28)
-
- Synthesis and biological evaluation of novel thiazolyl-coumarin derivatives as potent histone deacetylase inhibitors with antifibrotic activity
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New histone deacetylases (HDAC) inhibitors with low toxicity to non-cancerous cells, are a prevalent issue at present because these enzymes are actively involved in fibrotic diseases. We designed and synthesized a novel series of thiazolyl-coumarins, substituted at position 6 (R = H, Br, OCH3), linked to classic zinc binding groups, such as hydroxamic and carboxylic acid moieties and alternative zinc binding groups such as disulfide and catechol. Their in vitro inhibitory activities against HDACs were evaluated. Disulfide and hydroxamic acid derivatives were the most potent ones. Assays with neonatal rat cardiac fibroblasts demonstrated low cytotoxic effects for all compounds. Regarding the parameters associated to cardiac fibrosis development, the compounds showed antiproliferative effects, and triggered a strong decrease on the expression levels of both α-SMA and procollagen I. In conclusion, the new thiazolyl-coumarin derivatives inhibit HDAC activity and decrease profibrotic effects on cardiac fibroblasts.
- Pardo-Jiménez, Viviana,Navarrete-Encina, Patricio,Díaz-Araya, Guillermo
-
-
- Regioselective hydrodehalogenation of aromatic α-and β-halo carbonyl compounds by cui in isopropanol
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An operationally efficient and regioselective hydrodehalogenation methodology of aromatic α-and β-halo carbonyl compounds has been developed using CuI in isopropanol at 90 °C under basic condition. The catalytic system effectively dehalogenates chloride, bromide, and iodide groups and af-forded high yield (up to 97 %) as carbonyl compounds. The methodology is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically rich and poor substituents.
- Parveen, Iram,Khan, Danish,Ahmed, Naseem
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p. 759 - 764
(2019/01/09)
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- Proton Sensitive Functional Organic Fluorescent Dyes Based on Coumarin-imidazo[1,2-a]pyrimidine; Syntheses, Photophysical Properties, and Investigation of Protonation Ability
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A novel series of 2-coumarin-3-yl-imidazo[1,2-a]pyrimidines have been synthesized with functionalized coumarin and pyrimidine units of the different architecture to give various fluorescent compounds. A new additional series bearing unsubstituted coumarin and 7-dialkylaminocoumarin as fluorophore were obtained by palladium-catalyzed cross-coupling reactions, through coupling of 6-bromo-2-coumarin-3-yl-imidazopyrimidine derivatives with various arylboronic acids. In the all reaction step, microwave irradiation (MWI) method was used and compared with the conventional method (CM). Photophysical properties of synthesized compounds were studied by a combination of UV/Vis and fluorescence spectroscopy in various solvents having different polarities. The protonation abilities of all compounds were investigated by titration with trifluoroacetic acid (TFA) in dichloromethane. In both series, the compounds bearing 7-dialkylaminocoumarin are fluorescently active even in daylight and showed maximum absorption wavelengths (λabs–max) in the visible region in all solvents used. In addition, they showed drastic color and emission change in acidic environment. Moreover, for the investigation of protonation ability of three selected compounds bearing 7-dialkylaminocoumarin have been studied using a buffer solution with various pH and determinated their pKa values. The compound bearing morpholine has the potential to use as colorimetric and luminescence pH sensor. The thermal properties of all the synthesized compounds were also evaluated with TGA to test their usability as optic dyes.
- Ayd?ner, Burcu,Sefero?lu, Zeynel
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p. 5921 - 5934
(2018/11/23)
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- Synthesis, docking and ADME prediction of novel 1,2,3-triazole-tethered coumarin derivatives as potential neuroprotective agents
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In an attempt to find potential neuroprotective agents, a series of novel 3-(1-((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl) methoxyimino) ethyl)-2H-chromen-2-one derivatives 6a–j were synthesized by using “click reaction” and evaluated for their in vit
- Kumari, Maddineni Aruna,Rao, Chunduri Venkata,Triloknadh, Settypalli,Harikrishna, Nallapaneni,Venkataramaiah, Chintha,Rajendra, Wudayagiri,Trinath, Daggupati,Suneetha, Yeguvapalli
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p. 1989 - 2008
(2017/12/04)
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- Structure–activity relationship investigation of coumarin–chalcone hybrids with diverse side-chains as acetylcholinesterase and butyrylcholinesterase inhibitors
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Chalcones containing tertiary amine side-chains have potent activity as acetylcholinesterase (AChE) inhibitors. However, the effects of the location of the tertiary amine groups as well as of other groups on AChE and butyrylcholinesterase (BChE) activity have not been reported. Here, we report the synthesis and testing of 36 new coumarin–chalcone hybrids (5d–7j, 9d–11f, 12k–13m) against AChE and BChE. The nature and position of the chalcone substituents had major effects on inhibitory activity as well as selectivity for AChE over BChE. Compounds with para-substituted chalcone fragments in which the substituents were choline-like had potent activity against AChE and poor activity against BChE, while ortho-substituted analogs exhibited an opposite effect. Replacement of the terminal amine groups by amide, alkyl or alkenyl groups abrogated activity. Compound 5e showed potent inhibitory activity (IC50=0.15±0.01μmol/L) and good selectivity for AChE over BChE (ratio 27.4), and a kinetic study showed that 5e exhibited mixed-type inhibition against AChE. Computational docking results indicate that 5e binds to Trp 279, Tyr334 and Trp 84 in AChE, but only to Trp 82 in BChE. Overall, the results show that coumarin–chalcone hybrids with choline-like side-chains have promising activity and selectivity against AChE and be promising therapeutic leads for Alzheimer’s disease.
- Kang, Lu,Gao, Xiao-Hui,Liu, Hao-Ran,Men, Xue,Wu, Hong-Nian,Cui, Pei-Wu,Oldfield, Eric,Yan, Jian-Ye
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p. 893 - 906
(2018/06/26)
-
- Synthetic Approach Toward Heterocyclic Hybrids of [1,2,4]Triazolo[3,4- b ][1,3,4]thiadiazines
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The synthesis of novel heterocyclic [1,2,4]triazolo[3,4- b ][1,3,4]thiadiazine hybrids by a bimolecular reaction of 2-(4-amino-5-mercapto-4 H -[1,2,4]triazol-3-yl)phenol with an aromatic or heterocyclic α-bromoacetyl derivatives is described. This synthetic procedure starts from an unprotected phenol.
- Lechani, Nawel,Hamdi, Maamar,Kheddis-Boutemeur, Baya,Talhi, Oualid,Laichi, Yacine,Bachari, Khaldoun,Silva, Artur M. S.
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supporting information
p. 1502 - 1504
(2018/05/03)
-
- Coumarin-oxazole-vinyl alpha-glucosaccharase inhibitor as well as preparation method and application thereof
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The invention discloses a coumarin-oxazole-vinyl alpha-glucosaccharase inhibitor as well as a preparation method thereof. The method comprises the following steps: ensuring that a product generated after reaction of salicylaldehyde, ethyl acetoacetate and piperidine is subjected to mixing reaction with N-bromo-succinimide and para-toluenesulfonic acid, and then adding hexamethylenetetramine, so asto obtain white solid after reaction, feeding the obtained white solid into ethanol to dissolve the white solid, feeding concentrated hydrochloric acid, and ensuring that a product generated after reaction reacts with substituted cinnamyl aldehyde, iodine, tert-butyl hydroperoxide and sodium bicarbonate, so as to obtain the coumarin-oxazole-vinyl alpha-glucosaccharase inhibitor which can serve asa main material of an anti-diabetic medicine. The coumarin-oxazole-vinyl alpha-glucosaccharase inhibitor is clear in mechanism of action, stably reduces blood glucose, is safe and non-toxic, high andobvious in inhibitory activity, mature and simple in preparation method, easy to strictly control the quality in industrial production, and mild and non-toxic in preparation conditions, does not produce three wastes, and is environmentally friendly.
- -
-
Paragraph 0029; 0031
(2018/10/19)
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- Microwave enhanced synthesis of biocompelling substituted OXA/thiazoles via acetyl coumarin azomethine
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The present work deals with synthesis of substituted oxazoles (4a-d) and thiazoles (5a-d) starting with acetyl coumarin in eco-friendly conditions utilizing conventional and microwave energy for heteroannular ring formation via Schiff base. All synthesized compounds have been characterized by spectroscopic techniques and evaluated for anti-inflammatory, antioxidant, antibacterial, antitumor and phytotoxic activities. All the synthesized compounds were found to possess good anti-inflammatory, antitumor and antioxidant activity. Compounds (4a, 5a-d) were found to be remarkably effective inhibitors of Agrobacterium tumefaciens. Compounds 2a, 2b, 4b-d were mutation suppressors and possess bio-friendly effect on the dormancy of seeds and cell division or differentiation.
- Hussain, Erum Akbar,Naz, Narjis,Ghani, Ambreen,Yasmeen, Abida,Ishaque, Sobia
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p. 359 - 368
(2018/04/23)
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- Microwave-assisted debromination of α-bromoketones with triarylstibanes in water
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Several α-bromoarylketones were reacted with triarylstibanes under microwave irradiation in water to obtain the corresponding debrominated ketones. Under similar reaction conditions, 1,2-elimination of vic-dibromides in water afforded the corresponding E-olefins. This reaction is the first example of organoantimony compounds utilized for organic transformation in water.
- Murata, Yuki,Sugawara, Yoshiyuki,Matsumura, Mio,Kakusawa, Naoki,Yasuike, Shuji
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p. 1081 - 1084
(2017/11/17)
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- Development of hydrogelator-based gel-entrapped base catalysts (GEBCs) as heterogeneous basic catalysts for the synthesis of 3-acetylcoumarins
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New gel entrapped base catalysts (GEBCs) have been prepared by entrapping some organic and inorganic bases into a solid aqueous gel matrix. Sodium alginate, gelrite and carboxymethyl chitosan were studied for the preparation of GEBCs. The phase behaviour of binary systems (gelator + water) is well studied, but ternary systems (gelator + water + base) are not much studied. Addition of a base to a (gelator + water) system drastically affected the behaviour of the gel. The phase behaviour of ternary systems (gelator + water + base) was studied by developing the corresponding ternary phase diagrams. From this study, the promising homogeneous viscous phases were converted into hard, irreversible gel beads by cross-linking the gelator with divalent cations Ca2+, Ba2+ and Sr2+. These gel beads were studied for base entrapment efficiency and leaching of the base. The GEBCs were used for the condensation of salicylaldehydes and methyl/ethyl acetoacetate to obtain 3-acetylcoumarins.
- Korgavkar, Nilesh N.,Samant, Shriniwas D.
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p. 12422 - 12428
(2017/11/06)
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- Magnetic cellulose/Ag as a novel eco-friendly nanobiocomposite to catalyze synthesis of chromene-linked nicotinonitriles
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In this work, design, preparation and performance of magnetic cellulose/Ag nanobiocomposite as a recyclable and highly efficient heterogeneous nanocatalyst is described. Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) pattern, vibrating sample magnetometer (VSM) curve, field-emission scanning electron microscopy (FE-SEM) image, energy dispersive X-ray (EDX) analysis and thermogravimetric analysis/differential thermal analysis (TGA/DTA) were used for the characterization. Then, its activity was investigated in the synthesis of 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-phenylnicotinonitrile derivatives. The main advantages of the reaction are high yields and short reaction times. The remarkable magnetic property of the nanobiocomposite catalyst provides easy separation from the reaction mixture by an external magnet without considerable loss of its catalytic activity.
- Maleki, Ali,Movahed, Hamed,Ravaghi, Parisa
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p. 259 - 267
(2016/09/23)
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- Design, characterization, in vitro antibacterial, antitubercular evaluation and structure–activity relationships of new hydrazinyl thiazolyl coumarin derivatives
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Herein, we describe the synthesis of 11new thiazolyl coumarin derivatives and evaluation of their potential role as antibacterial and antituberculosis agents. The structures of the synthesized compounds were established by extensive spectroscopic studies (Fourier transform infrared spectroscopy, 1H-nuclear magnetic resonance, 13C-nuclear magnetic resonance, 2D-nuclear magnetic resonance and liquid chromatography–mass spectrometry) and elemental analysis. All synthesized compounds were assayed for their in vitro antibacterial activity against a few gram positive and gram negative bacteria and antituberculosis activity against Mycobacterium tuberculosis H37Rv ATCC 25618 by using colorimetric microdilution assay method. Nine derivatives showed moderate anti-bacterial and anti-tuberculosis activities against all the tested strains. The highest activity against all the pathogens including Mycobacterium tuberculosis was observed by compound 7c with MIC values ranging between 31.25–62.5 μg/mL, indicating that coumarin skeleton could indeed provide useful scaffold for the development of new anti-microbial drugs.
- KhanYusufzai, Samina,Osman, Hasnah,Khan, Mohammad Shaheen,Mohamad, Suriyati,Sulaiman, Othman,Parumasivam, Thaigarajan,Gansau, Jualang Azlan,Johansah, Norhaniza,Noviany
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p. 1139 - 1148
(2017/05/04)
-
- PEG-600 mediated one-pot reaction of 3-acetyl-2: H -chromen-2-one with heterylthiols and phenylthioureas using tetrabutylammonium tribromide as an efficient green reagent
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A simple method for the one-pot reaction of 3-acetyl-2H-chromen-2-one with different heterylthiols and phenylthioureas under green conditions using tetrabutylammonium tribromide (TBATB) as an efficient reagent has been described. 3-Acetyl-2H-chromen-2-one
- Srikrishna, Devulapally,Kumar Dubey, Pramod
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p. 5168 - 5175
(2017/07/11)
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- Design, synthesis and docking study of novel coumarin ligands as potential selective acetylcholinesterase inhibitors
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New coumaryl-thiazole derivatives with the acetamide moiety as a linker between the alkyl chains and/or the heterocycle nucleus were synthesized and in vitro tested as acetylcholinesterase (AChE) inhibitors. 2-(diethylamino)-N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)acetamide (6c, IC50 value of 43 nM) was the best AChE inhibitor with a selectivity index of 4151.16 over BuChE. Kinetic study of AChE inhibition revealed that 6c was a mixed-type inhibitor. Moreover, the result of H4IIE hepatoma cell toxicity assay for 6c showed negligible cell death. Molecular docking studies were also carried out to clarify the inhibition mode of the more active compounds. Best pose of compound 6c is positioned into the active site with the coumarin ring wedged between the residues of the CAS and catalytic triad of AChE. In addition, the coumarin ring is anchored into the gorge of the enzyme by H-bond with Tyr130.
- Sonmez, Fatih,Zengin Kurt, Belma,Gazioglu, Isil,Basile, Livia,Dag, Aydan,Cappello, Valentina,Ginex, Tiziana,Kucukislamoglu, Mustafa,Guccione, Salvatore
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p. 285 - 297
(2017/11/10)
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- PhI(OAc)2 mediated an efficient Knoevenagel reaction and their synthetic application for coumarin derivatives
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A phenyliododiacetate (PhI(OAc)2) mediated an efficient and novel protocol for the Knoevenagel reaction has been successfully accomplished. A base free, simple and straightforward method afforded wide substrate scope and good functional group tolerance, having high yields (80–92%) under environmentally benign and mild reaction conditions.
- Khan, Danish,Mukhtar, Sayeed,Alsharif, Meshari A.,Alahmdi, Mohammed Issa,Ahmed, Naseem
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supporting information
p. 3183 - 3187
(2017/07/18)
-
- Coumarin-benzimidazole hybrids as a potent antimicrobial agent: Synthesis and biological elevation
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Molecular hybridization approach is an emerging tool in drug discovery for designing new pharmacophores with biological activity. A novel, new series of coumarin-benzimidazole hybrids were designed, synthesized and evaluated for their broad spectrum antim
- Singh, L Ravithej,Avula, Srinivasa Rao,Raj, Sneha,Srivastava, Akanksha,Palnati, Gopala Reddy,Tripathi,Pasupuleti, Mukesh,Sashidhara, Koneni V.
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p. 954 - 961
(2017/09/05)
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- Cross-aldol reaction of 3-acetyl-2H-chromen-2-one by using Amberlyst 26A as catalyst
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Synthesis of a series of 3-acetylcoumarin-derived chalcones (1a–16a) was catalyzed with Amberlyst 26A in ethanol. Using reusable Amberlyst 26A and biobased solvent ethanol make this method highly ecofriendly and simple. Amberlyst 26A was found to be a highly effective catalyst for cross aldol reaction. The results shown that the method is operationally simple to implement with a wide scope of substrates.
- Er?at?r, Mehmet,Akba?lar, Dilek,Demirkol, Onur,Giray, E. Sultan
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supporting information
p. 68 - 77
(2016/12/30)
-
- Microwave-assisted synthesis and antitumor evaluation of a new series of thiazolylcoumarin derivatives
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A new series of thiazolylcoumarin derivatives was synthesized. The designed strategy embraced a molecular hybridization approach which involves the combination of the thiazole and coumarin pharmacophores together. The new hybrid compounds were tested for
- Gabr, Moustafa T.,El-Gohary, Nadia S.,El-Bendary, Eman R.,El-Kerdawy, Mohamed M.,Ni, Nanting
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p. 1114 - 1131
(2017/09/25)
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- (E)- N' - aryl methylene - 4 - (coumarin - 3 - yl) thiazole - 2 - acid radical jingjing apperception compound preparation and use
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The invention discloses a preparing method of (E)-N'-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide compound and its application. A formula (I) of the compound is shown as below. The preparing method includes: making salicylic aldehyde and ethyl acetoacetate into 3-acetylindole-2H-chromene-2-one, allowing bromization, cyclization and hydrazinolysis to obtain 4-(2-oxo-2H-chromene-3-yl)thiazole-2-hydrazine, and allowing the 4-(2-oxo-2H-chromene-3-yl)thiazole-2-hydrazine to react with substituted benzaldehydes to obtain the target compound. The compound can serve as a raw material for antiseptic medicine; the preparing method has the advantages that the raw materials are simple and easy to obtain and operating is convenient.
- -
-
Paragraph 0021; 0023-0025
(2017/08/08)
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- A coumarin - thiazole - indole alkone compound and its preparation and use
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The invention discloses coumarin-thiazole-indolone compounds, and a preparation method and application thereof. The compounds are disclosed as Formula (I). The preparation method comprises the following steps: reacting salicylaldehyde and ethyl acetoacetate to obtain 3-acetyl-2H-benzopyranyl-2-one, carrying out bromination, cyclization and hydrazinolysis reaction to obtain 4-(2-oxo-2H-benzopyranyl-3-yl)thiazolyl-2-formylhydrazine, and finally, reacting with various substituted isatin to obtain the target compounds. The compounds can be used as a raw material of antibacterial drugs. The preparation method has the advantage of simple and accessible raw materials, and is convenient to operate.
- -
-
Paragraph 0025-0027
(2017/08/10)
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- In vitro inhibition effects on erythrocyte carbonic anhydrase I and II and structure-activity relationships of cumarylthiazole derivatives
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Coumarin and heterocyclic compounds incorporating urea have clinical applications as antiepileptics, diuretics, and antiglaucoma agents due to their carbonic anhydrase inhibitory properties. We investigated inhibition of carbonic anhydrase I and II with a series of coumarylthiazole derivatives containing urea/thiourea groups. All the investigated compounds exhibited inhibitory activity on both hCA I and hCA II, with 1-(3-chlorophenyl)-3-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea being the strongest inhibitor. Structure–activity relationship study showed that most of urea derivatives were more inhibiting for hCA I and hCA II than thiourea derivatives. The electron-withdrawing groups at the phenyl ring increased the inhibitory activity compared to electron-donating groups.
- Kurt, Belma Z.,Sonmez, Fatih,Gokce, Basak,Ergun, Adem,Gencer, Nahit,Demir, Taki,Arslan, Oktay,Kucukislamoglu, Mustafa
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p. 506 - 511
(2016/10/03)
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- Regioselective transition metal-free acylation of coumarins via cross-dehydrogenative coupling reaction of coumarins and aldehydes
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A transition metal-free cross-dehydrogenative coupling reaction is described for the preparation of 3-acylcoumarins. Heating a mixture of a coumarin, an aldehyde, and the K2S2O8/Aliquat 336 system in chlorobenzene at 100 °C for 8 h regioselectively afforded the corresponding 3-acylcoumarin derivatives in good to excellent yields.
- Adib, Mehdi,Rajai-Daryasarei, Saideh,Pashazadeh, Rahim,Tajik, Mahnaz,Mirzaei, Peiman
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p. 3701 - 3705
(2016/07/26)
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- Application of iron-based metal-organic frameworks in catalysis: Oxidant-promoted formation of coumarins using Fe3O(BPDC)3 as an efficient heterogeneous catalyst
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An iron-based metal-organic framework, Fe3O(BPDC)3, was synthesized, and was characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR) spectroscopy, atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. The Fe-MOF could be used as an efficient heterogeneous catalyst for the synthesis of coumarins from salicylaldehydes and activated methylene compounds in the presence of tert-butyl hydroperoxide as the oxidant under base-free conditions. The Fe3O(BPDC)3 was more catalytically active for the synthesis of coumarins than other MOFs such as Cu2(BDC)2(BPY), Cu3(BTC)2, Cu2(BDC)2(DABCO), Ni2(BDC)2(DABCO), and Fe3O(BDC)3. This Fe-MOF also offered significantly higher catalytic activity for the transformation than that of common metal salts such as FeCl3, Fe(NO3)3, FeSO4, CuCl2, CuCl, Cu(NO3)2, and Ni(NO3)2. The Fe3O(BPDC)3 catalyst could be recovered and reused several times without significant degradation in catalytic activity. To the best of our knowledge, the oxidant-promoted formation of coumarins under heterogeneous catalysis conditions was not previously mentioned in the literature.
- Lieu, Thien N.,Nguyen, Khoa D.,Le, Dung T.,Truong, Thanh,Phan, Nam T. S.
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p. 5916 - 5926
(2016/08/05)
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- Coumarin-thiazole and -oxadiazole derivatives: Synthesis, bioactivity and docking studies for aldose/aldehyde reductase inhibitors
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In continuation of our previous efforts directed towards the development of potent and selective inhibitors of aldose reductase (ALR2), and to control the diabetes mellitus (DM), a chronic metabolic disease, we synthesized novel coumarin-thiazole 6(a–o) and coumarin-oxadiazole 11(a–h) hybrids and screened for their inhibitory activity against aldose reductase (ALR2), for the selectivity against aldehyde reductase (ALR1). Compounds were also screened against ALR1. Among the newly designed compounds, 6c, 11d, and 11g were selective inhibitors of ALR2. Whereas, (E)-3-(2-(2-(2-bromobenzylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one 6c yielded the lowest IC50 value of 0.16 ± 0.06 μM for ALR2. Moreover, compounds (E)-3-(2-(2-benzylidenehydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6a; IC50 = 2.94 ± 1.23 μM for ARL1 and 0.12 ± 0.05 μM for ARL2) and (E)-3-(2-(2-(1-(4-bromophenyl)ethylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6e; IC50 = 1.71 ± 0.01 μM for ARL1 and 0.11 ± 0.001 μM for ARL2) were confirmed as dual inhibitors. Furthermore, compounds 6i, 6k, 6m, and 11b were found to be selective inhibitors for ALR1, among which (E)-3-(2-(2-((2-amino-4-chlorophenyl)(phenyl)methylene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6m) was most potent (IC50 = 0.459 ± 0.001 μM). Docking studies performed using X-ray structures of ALR1 and ALR2 with the given synthesized inhibitors showed that coumarinyl thiazole series lacks the carboxylate function that could interact with the anionic binding site being a common ALR1/ALR2 inhibitors trait. Molecular docking study with dual inhibitor 6e also suggested plausible binding modes for the ALR1 and ALR2 enzymes. Hence, the results of this study revealed that coumarinyl thiazole and oxadiazole derivatives could act as potential ALR1/ALR2 inhibitors.
- Ibrar, Aliya,Tehseen, Yildiz,Khan, Imtiaz,Hameed, Abdul,Saeed, Aamer,Furtmann, Norbert,Bajorath, Jürgen,Iqbal, Jamshed
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p. 177 - 186
(2016/08/24)
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- Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives
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New secondary benzenesulphonamide-substituted coumarylthiazole derivatives were synthesized and their inhibitory effects on purified carbonic anhydrase I and II were evaluated using CO2 as a substrate. The result showed that all the synthesized
- Kurt, Belma Zengin,S?nmez, Fatih,Bilen, ?i?dem,Ergun, Adem,Gen?er, Nahit,Arslan, Oktay,Kucukislamoglu, Mustafa
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p. 991 - 998
(2016/10/09)
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- Gastroprotective activity of synthetic coumarins: Role of endogenous prostaglandins, nitric oxide, non-protein sulfhydryls and vanilloid receptors
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Natural or synthetic coumarins showed gastroprotective and antiulcer activity in animal models. In this study, we have synthetized twenty coumarins using classic methods to evaluate their gastroprotective effects on the ethanol/HCl-induced gastric lesion model in mice at 20?mg/kg. Among the coumarins synthetized, compounds 6 and 10 showed the greatest gastroprotective activity being as active as lansoprazole at 20?mg/kg and reducing gastric lesions by 75 and 76%, respectively. Then, in a second experiment, compounds 6 and 10 were re-evaluated in order to understand the possible mode of gastroprotective activity. Regarding coumarin 6, the protective effect was reduced by pre-treatment of the mice with N-ethylmaleimide and l-NAME suggesting that sulfhydryl compounds and endogenous nitric oxide are involved in its gastroprotective activity. While for coumarin 10 the effect was reduced by pre-treatment with indomethacin suggesting that prostaglandins are positively involved in its gastroprotective activity.
- Sepulveda, Beatriz,Quispe, Cristina,Simirgiotis, Mario,Torres-Benítez, Alfredo,Reyes-Ortíz, Johanna,Areche, Carlos,García-Beltrán, Olimpo
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supporting information
p. 5732 - 5735
(2016/11/25)
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- 3-(5-(Benzylideneamino)thiazol-3-yl)-2H-chromen-2-ones: A new class of alkaline phosphatase and ecto-5′-nucleotidase inhibitors
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A new series of 3-(2-(benzylideneamino)thiazol-4-yl)-2H-chromen-2-ones has been synthesized. The structures of the compounds were established by means of 1H and 13C NMR spectroscopy. All compounds were evaluated for their potential t
- Saeed, Aamer,Ejaz, Syeda Abida,Shehzad, Muddasar,Hassan, Sidra,Al-Rashida, Mariya,Lecka, Joanna,Sévigny, Jean,Iqbal, Jamshed
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p. 21026 - 21036
(2016/03/05)
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- Design, synthesis and biological evaluation of novel coumarin thiazole derivatives as α-glucosidase inhibitors
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A new series of coumarin thiazole derivatives 7a-7t were synthesized, characterized by 1H NMR, 13C NMR and element analysis, evaluated for their α-glucosidase inhibitory activity. The majority of the screened compounds displayed potent inhibitory activities with IC50 values in the range of 6.24 ± 0.07-81.69 ± 0.39 μM, when compared to the standard acarbose (IC50 = 43.26 ± 0.19 μM). Structure-activity relationship (SAR) studies suggest that the pattern of substitution in the phenyl ring is closely related to the biological activity of this class of compounds. Among all the tested molecules, compound 7e (IC50 = 6.24 ± 0.07 μM) was found to be the most active compound in the library of coumarin thiazole derivatives. Enzyme kinetic studies showed that compound 7e is a non-competitive inhibitor with a Ki of 6.86 μM. Furthermore, the binding interactions of compound 7e with the active site of α-glucosidase were confirmed through molecular docking. This study has identified a new class of potent α-glucosidase inhibitors for further investigation.
- Wang, Guangcheng,He, Dianxiong,Li, Xin,Li, Juan,Peng, Zhiyun
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p. 167 - 174
(2016/03/15)
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