- Synthesis, antimycobacterial activity and docking study of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives and related hydrazide-hydrazones
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A new convenient method for preparation of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives 5b–g and coumarin containing hydrazide-hydrazone analogues 4a–e was presented. The antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and cytotoxicity against the human embryonic kidney cell line HEK-293 were tested in vitro. All compounds demonstrated significant minimum inhibitory concentrations (MIC) ranging 0.28–1.69?μM, which were comparable to those of isoniazid. The cytotoxicity (IC50?>?200?μM) to the “normal cell” model HEK-293T exhibited by 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives 5b–e, was noticeably milder compared to that of their hydrazone analogues 4a–e (IC50 33–403?μM). Molecular docking studies on compounds 4a–e and 5b–g were also carried out to investigate their binding to the 2-trans-enoyl-ACP reductase (InhA) enzyme involved in M. tuberculosis cell wall biogenesis. The binding model suggested one or more hydrogen bonding and/or arene-H or arene-arene interactions between hydrazones or pyrazole-fused coumarin derivatives and InhA enzyme for all synthesized compounds.
- Angelova, Violina T.,Valcheva, Violeta,Pencheva, Tania,Voynikov, Yulian,Vassilev, Nikolay,Mihaylova, Rositsa,Momekov, Georgi,Shivachev, Boris
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- Design, synthesis and biological evaluation of novel benzo-α-pyrone containing piperazine derivatives as potential BRAFV600Einhibitors
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The increasingly acquired resistance to vemurafenib and side effects of known inhibitors motivate the search for new and more effective anti-melanoma drugs. In this Letter, virtual screening and scaffold growth were combined together to achieve new molecu
- Chen, Long-Wang,Wang, Ze-Feng,Zhu, Bo,Man, Ruo-Jun,Liu, Yan-Dong,Zhang, Yuan-Heng,Wang, Bao-Zhong,Wang, Zhong-Chang,Zhu, Hai-Liang
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- Metal- and Catalyst-Free One-Pot Cascade Coupling of α-Enolic Dithioesters with in situ Generated 4-Chloro-3-formylcoumarin: Access to Thioxothiopyrano[3,2-c]chromen-5(2H)-ones
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An efficient and viable one-pot protocol for the synthesis of a specific class of 2-thioxothiopyrano[3,2-c] chromen-5(2H)-ones has been devised by the cross-coupling of 4-hydroxycoumarin and α-enolic dithioesters under metal- and additive-free conditions in open air. The reaction proceeds via in situ generation of 4-chloro-3-formylcoumarin followed by consecutive Michael-type addition/intramolecular cyclization/ elimination cascade, enabling the creation of thiopyran-2-thione ring over coumarin framework through successive formation of C?C and C?S bonds. Remarkably, the benign conditions, atom-economy, and quantifying forbearance of a wide horizon of functional groups are added characteristics to this strategy. (Figure presented.).
- Yadav, Dhananjay,Ansari, Monish A.,Kumar, Mitilesh,Singh, Maya Shankar
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- In vitro and in silico evaluation of chromene based aroyl hydrazones as anticonvulsant agents
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Series of aroyl hydrazones of 2H-chromene and coumarin carbaldehydes were synthesized and evaluated for their anticonvulsant activity and neurotoxicity. Further docking study on gamma-aminobutyric acid receptor was performed to elucidate their mechanisms of action. The highest protection was demonstrated by 2-furyl substituted 2H-chromene 8b in the maximal electroshock test (ED50 = 12.51 mg kg?1, PI MES > 23.98) and the subcutaneous pentylenetetrazole tests (ED50 = 127.10 mg kg?1). Furyl-substituted derivative 4b (ED50 = 68.66 mg kg?1) was the most active in the maximal electroshock test while methoxyphenyl-substituted derivate 4c was the most active in the 6-Hz test (ED50 = 94.34 mg kg?1). None of the compounds displayed neurotoxicity in the rota-rod test. In silico assessment of their blood-brain barrier permeability indicated them as central nervous system active agents. The results suggest that coumarin/2H-chromene aroyl hydrazones scaffold deserve further evaluation in models of epilepsy and derivatization.
- Angelova, Violina T.,Voynikov, Yulian,Andreeva-Gateva, Pavlina,Surcheva, Slavina,Vassilev, Nikolay,Pencheva, Tania,Tchekalarova, Jana
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- Spectroscopic, invitro antibacterial, and antifungal studies of Co(II), Ni(II), and Cu(II) complexes with 4-chloro-3-coumarinaldehyde Schiff bases
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A series of metal complexes ML2 2H2O [M = Co(II), Ni(II), and Cu(II)] have been synthesized with Schiff bases derived from 3-substituted-4-amino-5-mercapto-1,2,4-triazole and 4-chloro-3-coumarinaldehyde. The structures of these metal complexes have been proposed from elemental analyses, spectral (IR, UV-Vis, FAB-mass, ESR, and fluorescence), magnetic, and thermal studies. Low molar conductance values in DMF indicate that the metal complexes are non-electrolytes. Cyclic voltammetric studies suggested that the Ni(II) and Cu(II) complexes are single-electron transfer quasi-reversible. The Schiff bases and their metal complexes have been screened for invitro antibacterial (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Salmonella typhi) and antifungal activities (Candida albicans, Cladosporium, and Aspergillus niger) by the minimum inhibitory concentration method. The Schiff base I and its Co(II) and Ni(II) complexes exhibit DNA cleavage activity on isolated DNA of S. aureus and A. niger.
- Patil, Sangamesh A.,Unki, Shrishila N.,Kulkarni, Ajaykumar D.,Naik, Vinod H.,Kamble, Udaykumar,Badami, Prema S.
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- Synthesis of some novel spiro substituted pyrido[2,3-c]coumarins by exploring ‘tertiary amino effect’ reaction strategy
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Some novel spiro substituted pyrido[2,3-c]coumarin derivatives were synthesized from 4-hydroxycoumarin by exploring ‘tertiary amino effect’ reaction strategy.
- Borah, Pallabi,Bhuyan, Pulak J.
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- One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multicomponent reactions and their molecular switching properties
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Two new pyranocoumarins were synthesized via one-pot, microwave-assisted pseudo multicomponent condensations of coumarin and 4-methylquinoline to investigate their molecular switching properties. Both are light-sensitive and have a distinct change of color upon UV irradiation. The reaction can be reverted by treating the photogenerated products with imidazoline-functionalized magnetic nanoparticles, which can be swiftly recycled with an external permanent magnet.
- Li, Kuan-Ting,Lin, Yong-Bo,Yang, Ding-Yah
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- Antimycobacterial activity of novel hydrazide-hydrazone derivatives with 2H-chromene and coumarin scaffold
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This study reports the synthesis of new 2H-chromene or coumarin based acylhydrazones, which were evaluated for their in vitro antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and compared to the first-line antituberculo
- Angelova, Violina T.,Valcheva, Violeta,Vassilev, Nikolay G.,Buyukliev, Rosen,Momekov, Georgi,Dimitrov, Ivan,Saso, Luciano,Djukic, Mirjana,Shivachev, Boris
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- A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative
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Thermolysis of a coumarin trichloroacetimidate yields a single rearrangement product. The proposed mechanism is a pseudopericyclic allowed (Woodward-Hoffman forbidden) [3,5]-sigmatropic rearrangement to form the corresponding amide followed by a sigmatropic [1,5]-hydrogen migration. Transition state calculations at the B3LYP/6-31G(d,p) level support this mechanism and suggest the selectivity is influenced by the stability of the intermediates.
- Rajale, Trideep,Sharma, Shikha,Unruh, Daniel K.,Stroud, Daniel A.,Birney, David M.
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- Synthesis and structure of Schiff bases derived from 3-formyl-4- hydroxycoumarin and diamines
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The mono- and diimine products from the condensation of 3-formyl-4-hydroxycoumarin and various diamines were synthesized. It was shown by 1H NMR and mass spectrometry that the obtained compounds in DMSO-d6 solution and in gas phase exist in the E- and Z-keto-enamine forms.
- Milevskii,Chibisova,Solov'Eva,Anisimova,Lebedev,Ivanov,Traven
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- Coordination chemistry of rare earth metal complexes with coumarin-based imines: Ecofriendly synthesis, characterization, antimicrobial, DNA cleavage, pesticidal, and nematicidal activity evaluations
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Coordination and biocidal aspects of lanthanide(III) complexes with 3-formyl-4-chlorocoumarin hydrazinecarbothioamide (L1H) and 3-formyl-4-chlorocoumarin hydrazinecarboxamide (L2H) are described with the support of elemental analyses, molecular weight, melting point, and molar conductance determinations along with the IR, 1H NMR, EPR, UV spectral, and X-ray powder diffraction studies. The spectral data suggest that the ligands are monobasic bidentate, coordinating through nitrogen and sulfur/oxygen. The isolated products are colored solids, soluble in DMSO, DMF, and methanol. All the complexes are monomeric, as indicated by their molecular weight determinations. Conductivity measurements in dry DMF show them to be non-electrolytes. The antimicrobial, DNA cleavage, pesticidal, and nematicidal activities were examined and are discussed. Copyright
- Kapoor, Puja,Singh,Fahmi, Nighat
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- The Vilsmeier reaction in the synthesis of 3-substituted [1]Benzopyrano[4,3-b]pyridin-5-ones. An unusual pyridine ring closure
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Starting from 4-chlorocoumarin-3-carbaldehyde (1) and Wittig phosphoranes 2a-d the title compounds 6a-c have been synthesized via a four-step sequence. The intermediate 4-alkylamino-3-vinylcoumarins 5a-k have been prepared by the reaction of 4-chloro-3-vinylcoumarins 3a-d with primary amines 4a-h. The coumarin derivatives 5 (except 5k) underwent an unusual pyridine ring closure under Vilsmeier conditions to form the benzopyrano[4,3-b]pyridines 6. When the aminoaldehydes 7 were treated with the Wittig reagent 2b the fused N-alkyl-2(1H)-pyridinones 8 have been obtained as expected.
- Heber,Ivanov,Karagiosov
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- Coumarin based colorimetric and fluorescence on-off chemosensor for F?, CN? and Cu2 + ions
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(E)-4-Chloro-3-[{2-(4-nitrophenyl)hydrazono}methyl]-2H-chromen-2-one (C), a coumarin derivative has been studied toward its ion sensing properties for F?, CN? and Cu2 +. A proton-transfer mechanism for F? sensing has been deduced with the help of 1H NMR titration alongwith from the changes in the absorption and emission spectra of C in the presence of F?. C formed 1:1 stoichiometric complex with each of these analytes. Sensing of C toward Cu2 + is poor, but interestingly in the presence of F? or CN? the sensing ability of Cu2 + gets enhanced many folds, and C can act as F? or CN? mediated off-on sensor for Cu2 +. Moreover, colorimetric strip (pre-coated with the coumarin derived compound) tests for F? and CN? from their DMSO solution at high temperature (~ 100 °C) opens up the door for easiest naked eye recognition and distinction of these ions, and also for naked-eye detection of F? and CN? from its aqueous solution at high temperature (~ 100 °C).
- Roy, Debashis,Chakraborty, Arijit,Ghosh, Rina
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- Design, synthesis and biological evaluation of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates containing sulfonamido as potential PI3Kα inhibitors
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A series of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates contained sulfonamido were designed and synthesized, and their anticancer effects in vitro was evaluated to develop some new PI3Kα inhibitors. Most of desired compounds exhibited the better antiproliferative activities against four cancer cell lines than that of LY294002. Out of them, compound 4o displayed the potent antiproliferative activity and high selectivity against the PI3Kα protein and it can induce apoptosis of HCT116 in a dose-dependent manner. Western blot assay indicated that compound 4o obviously down-regulated expression of p-Akt (S473). Molecular docking was performed to clarify the possible binding mode between compound 4o and PI3Kα. All these results indicated that compound 4o could be a potential inhibitor of PI3Kα.
- Yin, Yong,Hu, Jia-Qin,Wu, Xu,Sha, Shao,Wang, She-Feng,Qiao, Fang,Song, Zhong-Cheng,Zhu, Hai-Liang
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- Discovery of chromeno[4,3-c]pyrazol-4(2H)-one containing carbonyl or oxime derivatives as potential, selective inhibitors PI3Kα
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A series of novel chromeno[4,3-c]pyrazol-4(2H)-one containing carbonyl or oxime derivatives (4a-n, 5a-n) have been synthesized and evaluated their biological activities as phosphatidyl inositol 3-kinase (PI3K) inhibitors. Out of them, compound 5l showed the most potent antiproliferative activities against HCT-116 with IC50 of 0.10 μM in vitro, and exhibited the most potent activity for PI3Kα with the value of 0.012 μM. Docking simulation of 5l into PI3Kα active site were performed to determine the probable binding model, and it indicated that compound 5l could be optimized as a potential inhibitor of PI3Kα in the further study.
- Lu, Liang,Sha, Shao,Wang, Kai,Zhang, Yuan-Heng,Liu, Yan-Dong,Ju, Guo-Dong,Wang, Baozhong,Zhu, Hai-Liang
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- The novel coumarin[3,2-c]thiophene and its hydroxamic acid and ureido derivatives: Synthesis and cytostatic activity evaluations
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In the present paper, we report on the synthesis and in vitro antitumour effects of novel hydroxamic acid (compounds 4 and 5) and ureido (compounds 7-11) derivatives containing coumarin[3,2-c]thiophene moiety. The results of antiproliferative assays perfo
- Wittine, Karlo,Ratkaj, Ivana,Benci, Kre?imir,Suhina, Tomislav,Mandi?, Leo,Ili?, Nata?a,Paveli?, Sandra Kraljevi?,Paveli?, Kre?imir,Mintas, Mladen
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- An efficient synthesis of 4-substituted coumarin derivatives via a palladium-catalyzed Suzuki cross-coupling reaction
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An efficient Pd-catalyzed Suzuki cross-coupling reaction of sterically crowded 4-chlorocoumarin derivatives with air- and moisture-stable potassium organotrifluoroborates is developed. This methodology has been used to generate a series of novel alkyl, ar
- Rajale, Trideep,Sharma, Shikha,Stroud, Daniel A.,Unruh, Daniel K.,Miaou, Emily,Lai, Kimberly,Birney, David M.
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- The behavior of 4-azidocoumarin-3-carboxaldehyde towards certain sulfur reagents and primary amines
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The behavior of 4-azidocoumarin-3-carboxaldehyde (1) towards certain sulfur reagents such as isothiocyanates (2a-c), thionyl chloride, Lawesson's reagent (LR, 3), and phosphorus pentasulfide as well as towards primary amines such as glycine (4) and towards anthranilic acid (5) was investigated. The structures of the new products were attested by suitable analytical and spectroscopic measurements. Taylor & Francis Group, LLC.
- Ibrahim, Nabila M.,Yosef, Hisham Abdallah A.,Yakout, El-Sayed M. A.,Mahran, Mohamed Refat H.
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- Synthesis, spectroscopic characterization, antimicrobial, pesticidal and nematicidal activity of some nitrogen-oxygen and nitrogen-sulfur donor coumarins based ligands and their organotin(IV) complexes
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Series of new tin complexes are synthesized by classical thermal and microwave-irradiated techniques. The biologically potent ligands 3-formyl-4-chlorocoumarin semicarbazone (L1H) and 3-formyl-4-chlorocoumarin thiosemicarbazone (L2H), were prepared by the condensation of semicarbazide hydrochloride and thiosemicarbazide in ethanol with the particular ketone by using microwave as well as conventional methods. The tin(IV) complexes have been prepared by mixing Ph3SnCl/Me 3SnCl/Me2SnCl2 in 1:1 and 1:2 molar ratios with monofunctional bidentate ligands. The structures of the ligands and their tin complexes were confirmed by the elemental analysis, melting point determinations, molecular weight determinations, IR, 1H NMR, 13C NMR, 119Sn NMR, UV, mass spectral and X-ray powder diffraction studies. On the basis of these studies it is clear that the ligands coordinated to the metal atom in a monobasic bidentate mode, by X ∩ N donor system. Thus, suitable trigonal bipyramidal geometry for penta-coordinated state and octahedral geometry for hexa-coordinated state have been suggested for the 1:1 and 1:2 metal compounds. Both the ligands and their complexes have been screened for their antimicrobial, pesticidal and nematicidal activities. Copyright
- Dawara, Latika,Singh
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- Pd-Catalyzed cross-coupling synthesis of 4-aryl-3-formylcoumarins
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The threefold cross-coupling of triarylbismuth reagents with 4-chloro-3-formylcoumarins furnished the corresponding 4-aryl-3-formylcoumarins in a chemoselective manner with high yields under Pd-catalyzed conditions. This method was successfully applied to electronically different triarylbismuth reagents and 4-chloro-3-formylcoumarins preserving the 3-formyl group in the coumarin scaffold.
- L. N. Rao, Maddali,Nand, Sachchida
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supporting information
p. 1053 - 1057
(2022/02/11)
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- Syntheses, characterization, antimicrobial and DNA cleavage activity of Cr(III) complexes with coumarin based schiff base ligands
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A series of biologically important complexes of chromium(III) have been synthesized by the reaction of 3-formyl-4-chlorocoumarin hydrazinecarbothioamide (L1H) and 3-formyl-4-chlorocoumarin hydrazinecarboxamide (L2H) with CrCl3·6H2O in 1:1 and 1:2 molar ratio. All the complexes have been characterized by elemental analysis, molecular weight determination, melting point, conductivity measurements, electronic, IR, 1H NMR, 13C NMR and EPR spectroscopic techniques and X-ray diffraction. In vitro biological screening effects of the compounds were tested against the pathogenic bacterial and fungal species. Further, free ligands and their metal complexes have been screened for their DNA cleavage activity. A comparative study of the biological activities of the Schiff base ligands and their Cr(III) complexes indicates that the complexes exhibit higher antimicrobial and DNA cleavage activity than the free ligands. Physicochemical studies and spectral data suggested a hexa-coordinated environment around the central metal ion.
- Fahmi, Nighat,Kumari, Anita,Meena, Ramhari,Sharma, Naveen
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p. 2982 - 2988
(2021/12/14)
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- Coumarin-triazole hybrids: Design, microwave-assisted synthesis, crystal and molecular structure, theoretical and computational studies and screening for their anticancer potentials against PC-3 and DU-145
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This study presents the synthesis of series of α,β-unsaturated carbonyl linked coumarin-triazole hybrids, 7(a-e) by microwave irradiation conditions. The target compounds were synthesized in four steps starting from 4-hydroxycoumarin, 1 and substituted aromatic primary amines, 3. Spectroscopic analysis provide the structure proofs of synthesized new compounds 6e and 7(a-e), and the molecular structure of one of the intermediate compound 6e was confirmed by single crystal X-ray diffraction studies. The crystal structure analysis shows that the C-H…π, C-O…π and π—π intermolecular interactions stabilizes the crystal structure, the intermolecular interactions are quantified through Hirshfeld surface analysis. To substantiate the X-ray crystal structure, the density functional theory calculations were performed. Further, the target compounds coumarin-triazole hybrids, were screened in vitro for their anticancer activity against PC-3 and DU-145 cell lines. The result shows that, amongst the series, compound 7c was more potent against PC-3 and DU-145 cell lines.
- Vagish, Channa Basappa,Kumara, Karthik,Vivek, Hamse Kameshwar,Bharath, Srinivasan,Lokanath, Neratur Krishnappagowda,Ajay Kumar, Kariyappa
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- Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates
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Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.
- Bhimapaka, China Raju,Karri, Shailaja,Kuncha, Madhusudana,Kurma, Siva Hariprasad,Sistla, Ramakrishna
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supporting information
(2020/06/22)
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- Formation of epoxychromeno[4,3-c]isoquinolines through diastereoselective one-pot IMDA reaction of 4-chloro-3-[(1E)-3-oxo-3-phenyl-1-propen-1-yl]-2H-chromen-2-one and furfurylamine
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Abstract: An intramolecular Diels–Alder mediated reaction of (2E)-3-(4-chloro-2-methylene-2H-chromen-3-yl)-1-phenyl-2-propen-1-one, which was obtained in situ from the reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde and Wittig reagent, with furfuryl
- Alizadeh, Abdolali,Amir Ashjei Asalemi, Kaveh,Farajpour, Behnaz,Halvagar, Mohammad Reza
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p. 3393 - 3399
(2020/07/20)
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- Design, synthesis, bioactivity, and computational studies of some morpholine-clubbed coumarinyl acetamide and cinnamide derivatives
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Abstract: The novel derivatives of morpholine-clubbed 3-substituted coumarinyl acetamide and cinnamide derivatives 5a–5j and 6a–6j have been synthesized via various 2-chloro-N-phenyl acetamide and cinnamoyl chloride derivatives, respectively. The required motif has been generated through Vilsmeier–Haack reaction on 4-hydroxycoumarin annelation of morpholine followed by imine formation and subsequently condensation with various 2-chloro-N-phenylacetamide and cinnamoyl chloride to furnish the desired molecule. The synthesized molecules were characterized by various spectroscopic methods viz IR, 1H NMR, 13C NMR. Their antimicrobial activities against various strains of bacteria and fungi have been evaluated, and computational studies have also been performed for all the newly synthesized analogs. Graphical Abstract: [Figure not available: see fulltext.].
- Chauhan, Prakashsingh M.,Thummar, Sandeep N.,Chikhalia, Kishor H.
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p. 1261 - 1277
(2018/05/22)
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- Unexpected synthesis of three components from the reaction of 4-chloro-3-formylcoumarin with hydroxylamine hydrochloride
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A mild and simple oximation reaction of 4-chloro-3-formylcoumarin with hydroxylamine hydrochloride in basic medium gave unexpected three components via oxime.Those compounds were separatedin good yields by preparative TLC and by chemical means using diffe
- Elkhateeb, Ahmed,Alshehri, Ashwag S.,Kirsch, Gilbert,Abdel-Hafez
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p. 379 - 384
(2016/05/09)
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- An efficient route for synthesis and reactions of seleno[2, 3-c]coumarin
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Synthesis of new selenium-containing coumarin moiety via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selenium and sodium borohydride gave 3-cyano-4-coumarinselenol which reacted with different halo-acids, such as chloroacetonitrile, eth
- Abdel-Hafez, Shams H.,Elkhateeb, Ahmed,Gobouri, Adel A.,El Azab, Islam H.,Kirsch, Gilbert
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p. 1054 - 1062
(2016/07/06)
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- Coumarin sulfonamides derivatives as potent and selective COX-2 inhibitors with efficacy in suppressing cancer proliferation and metastasis
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Cyclooxygenase-2 is frequently overexpression in malignant tumors and the product PGE2promotes cancer cell progression and metastasis. We designed novel series of coumarin sulfonamides derivatives to improve biological activities of COX-2 inhib
- Lu, Xiao-Yuan,Wang, Zhong-Chang,Ren, Shen-Zhen,Shen, Fa-Qian,Man, Ruo-Jun,Zhu, Hai-Liang
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supporting information
p. 3491 - 3498
(2016/07/21)
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- Design and synthesis for coumarin piperazine antineoplastic compound
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The invention discloses a coumarin piperazine derivative and a preparing method thereof.The structure of the coumarin piperazine derivative is shown in the formula (please see the formula in the description), wherein R1 is selected from -CH2CH3 and others shown in the description.
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Paragraph 0023; 0024; 0025
(2016/10/10)
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- Diastereoselective synthesis of novel tetra-and pentacyclic annulated coumarino-δ-sultam pyrrolidine, pyrrolizidine, pyrrolothiazole and isoxazolidine derivatives: Via intramolecular 1,3-dipolar cycloadditions
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A facile and efficient strategy towards the novel tetra- and pentacyclic annulated coumarino-δ-sultam pyrrolidine, pyrrolizidine, pyrrolothiazole and isoxazolidine via intramolecular 1,3-dipolar cycloadditions of nitrones or azomethine ylides is described
- Ghandi, Mehdi,Zarezadeh, Nahid,Abbasi, Alireza
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p. 67805 - 67816
(2016/08/02)
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- Antiproliferative and antioxidative effects of novel hydrazone derivatives bearing coumarin and chromene moiety
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[InlineMediaObject not available: see fulltext.] A series of new hybrid molecules with a hydrazone fragment were synthesized and characterized by Fourier transform-infrared spectroscopy, nuclear magnetic resonance, mass spectrometry, and elemental analysi
- Angelova, Violina T.,Vassilev, Nikolay G.,Nikolova-Mladenova, Boryana,Vitas, Jasmina,Malba?a, Radomir,Momekov, Georgi,Djukic, Mirjana,Saso, Luciano
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p. 2082 - 2092
(2016/10/03)
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- Carbohydrate hydrolyzing enzymes inhibitory and free radical scavenging activities of substituted 2H-chromene-3-carboxylates, 2H-chromenyl Knoevenagel derivatives and 6H-chromenoquinolinones
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Three series of compounds namely ethyl 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates 3a-q, 2H-chromenyl Knoevenagel derivatives 7a-j and 6H-chromenoquinolinones 9a-l have been prepared. The synthesized compounds 3a-q, 7a-j and 9a-g have been screened for anti-oxidant and anti-diabetic activity. Compound 3i shows the most potent ABTS inhibitory activity when compared to trolox. Compounds 3b, 3d, 3j and 3l show α-amylase inhibitory activity.
- Vishnu,Srikanth,Tiwari, Ashok K.,Kumar, D. Anand,Raju, B. China
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p. 1332 - 1341
(2015/11/10)
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- Carbohydrate hydrolyzing enzymes inhibitory and free radical scavenging activities of substituted 2H-chromene-3-carboxylates, 2H-chromenyl Knoevenagel derivatives and 6H-chromenoquinolinones
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Three series of compounds namely ethyl 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates 3a-q, 2H-chromenyl Knoevenagel derivatives 7a-j and 6H-chromenoquinolinones 9a-l have been prepared. The synthesized compounds 3a-q, 7a-j and 9a-g have been screened for anti-oxidant and anti-diabetic activity. Compound 3i shows the most potent ABTS inhibitory activity when compared to trolox. Compounds 3b, 3d, 3j and 3l show α-amylase inhibitory activity.
- Vishnu,Srikanth,Tiwari, Ashok K.,Kumar, D. Anand,Raju, B. China
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p. 1332 - 1341
(2016/02/23)
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- The novel derivatives of 3-(iminomethyl)-2H-chromen-2-one with thiourea and piperazine structural motive: Rationale, synthesis, antimicrobial and anti-tb evaluation
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The emergence and rapid spread of Multi Drug Resistant (MDR) infectious microbial flora embracing a variety of bacterial, fungal as well as mycobacterium strains are causing a threat to public health worldwide. To cure this dilemma, a library of two serie
- Lakum, Harshad P.,Shah, Dhruvin R.,Chikhalia, Kishor H.
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p. 324 - 341
(2015/04/14)
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- Diversified construction of chromeno[3,4-c]pyridin-5-one and benzo[c]chromen-6-one derivatives by domino reaction of 4-Alkynyl-2-oxo-2H- chromene-3-carbaldehydes
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Silver-catalyzed three-component, tandem reactions of 4-alkynyl-2-oxo-2H- chromene-3-carbaldehydes, amines and various nucleophiles result in the formation of highly functionalized chromeno[3,4-c]pyridin-5-ones in high yields. Gold-catalyzed [4+2] cycloadditions of 4-alkynyl-2-oxo-2H-chromene-3- carbaldehydes with alkynes or alkenes have also been achieved to afford benzo[c]chromen-6-ones efficiently.
- Xiao, Jian,Chen, Yuye,Zhu, Shuai,Wang, Liang,Xu, Lubin,Wei, Hongtao
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p. 1835 - 1845
(2014/06/09)
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- Novel 2H-chromen derivatives: Design, synthesis and anticancer activity
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A series of novel dihydropyrazole derivatives linked with 2H-chromen were designed and synthesized. All of the compounds have been screened for their antiproliferative activity against MGC-803, Bcap-37, SGC-7901 and HepG 2 cell lines in vitro. The results revealed that compounds 4a and 10a exhibited strong inhibitory activity against HepG2 cell and manifested obvious un-toxic effect on GES-1 and L-02 cell lines. Some title compounds were tested against telomerase, compound 10a showed the most potent inhibitory activity with IC50 value at 0.98 ± 0.11 μM, it could fit well into the active site of TERT. The further molecular mechanism of antiproliferation was explored, the data suggested that compound 10a could inhibit hTERT expression and Wnt/β-catenin signaling.
- Qiang, Dong Zhi,Shi, Jing Bo,Song, Bao An,Liu, Xin Hua
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p. 5607 - 5617
(2014/01/23)
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- Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis
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A series of sulfonamides containing coumarin moieties had been prepared that showed a very interesting profile for the inhibition of two human carbonic anhydrase inhibitors. These compounds were evaluated for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA II and the tumor-associated isozyme hCA IX. The most potent inhibitor against hCA II and IX were compounds 5d (IC50 = 23 nM) and 5l (IC50 = 24 nM), respectively. These sulfonamides containing coumarin moieties may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly. Eighteen compounds were scrutinized by CoMFA and CoMSIA techniques of 3D quantitative structure-activity relationship. Nine of the compounds were evaluated for cytotoxicity against human macrophage.
- Wang, Zhong-Chang,Qin, Ya-Juan,Wang, Peng-Fei,Yang, Yong-An,Wen, Qing,Zhang, Xin,Qiu, Han-Yue,Duan, Yong-Tao,Wang, Yan-Ting,Sang, Ya-Li,Zhu, Hai-Liang
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- Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates
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2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H) -ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100°C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed.
- Kumar, J. Ashok,Saidachary,Mallesham,Sridhar,Jain, Nishant,Kalivendi, Shashi Vardhan,Rao, V. Jayathirtha,Raju, B. China
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p. 389 - 402
(2013/10/01)
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- Synthesis of 4-Aminocoumarin derivatives with N-Substitutents containing hydroxy or amino groups
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Reactions of 4-hydroxycoumarin (1a) and 4-chlorocoumarin-3-carbaldehyde (1b) with amino alcohols or alkylene diamines led to the formation of the corresponding N-substituted 4-aminocoumarins 3, 5 and 6. However, 4-hydroxycoumarin-3-carbaldehyde (8) reacted with 2-aminoethanol and ethylenediamine to give N-substituted 3-(aminomethylene)-chromane-2,4-diones 9a, b. The structure and the E-configuration of compound 6 were proven by X-ray crystal structure analysis. Products 9a, b displayed signals of both E-and Z-isomers in their NMR spectra. All novel products have been characterized by means of spectral (IR, NMR, MS) data and elemental analyses.
- Ivanov, Ivo C.,Angelova, Violina T.,Vassilev, Nikolay,Tiritiris, Ioannis,Iliev, Boyan
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p. 1031 - 1040
(2013/09/24)
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- Synthesis and antimicrobial activity of new heterocyclic compounds containing thieno[3,2-c]coumarin and pyrazolo[4,3-c]coumarin frameworks
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Reaction of 4-chlorocoumarin-3-carbonitrile with ethyl thioglycolate and ethyl glycinate hydrochloride leads to a series of title products. Hydrazinolysis of amino thienocoumarin carboxylate afforded the hydrazino derivative which underwent various reactions to build new heterocyclic rings containing thienocoumarin moiety. Chloro acetylation of aminoester compound afforded the chloro acetyl amino which underwent nucleophilic substitution reactions with various amines. The following treatment with formaldehyde under Mannich conditions afforded the corresponding imidazo derivatives. Reaction of chloroacetylamino with potassium thiocyanate yielded ethylpyrimidothieno coumarin sulfanylacetate which was used as a versatile precursor for synthesis of other heterocycles. On the other hand, reaction of chloro coumarin carbonitrile with hydrazine gave the aminopyrazolocoumaine which reacted with bifunctionally compounds to give the substituted pyrimido derivatives. Diazotization and coupling of aminopyrazole with ethylcyanoacetate yielded ethylaminotriazinopyrazolocoumarine carboxylate. Several of the compounds obtained demonstrated considerable antifungal and antibacterial activity in the in vitro test systems.
- El-Dean, Adel M. Kamal,Zaki, Remon M.,Geies, Ahmed A.,Radwan, Shaban M.,Tolba, Mahmoud S.
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p. 553 - 564
(2013/10/21)
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- NIR-fluorescent coumarin-fused BODIPY dyes with large Stokes shifts
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A series of novel non-symmetrical coumarin-fused BODIPY dyes were synthesised. Their absorption and emission properties are strongly influenced by substitution in the coumarin moiety. Diethylamino-substituted dyes showed near-IR emission with large Stokes shifts (up to 144 nm) and good fluorescence quantum yields.
- Bochkov, Andrei Y.,Akchurin, Igor O.,Dyachenko, Oleg A.,Traven, Valery F.
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p. 11653 - 11655
(2013/12/04)
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- One-pot synthesis of biaryl lactones by Sonogashira cross-coupling reactions of 4-chloro-3-formylcoumarin and subsequent domino [5+1] cyclization/deacetylation reactions with 1,3-dicarbonyl compounds
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Biaryl lactones were prepared by a new palladium(0) and base-catalyzed one-pot reaction of 4-chloro-3-formylcoumarin with alkynes and 1,3-dicarbonyl compounds. Copyright
- Iaroshenko, Viktor O.,Abbasi, Muhammad S. A.,Villinger, Alexander,Langer, Peter
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supporting information; experimental part
p. 803 - 806
(2012/05/04)
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- Synthesis of some tetrazole fused pyrido[2,3-c]coumarin derivatives from a one-pot three-component reaction via intramolecular 1,3-dipolar cycloaddition reaction of azide to nitriles
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Some novel tetrazole fused pyrido[2,3-c]coumarin derivatives 5/7/9 were synthesized from a one-pot three-component reaction of 4-chloro-3- formylcoumarins 2, sodium azide 3, and alkyl/aryl acetonitriles 4/6/8.
- Borah, Pallabi,Seetham Naidu, P.,Bhuyan, Pulak J.
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p. 5034 - 5037,4
(2020/07/31)
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- Synthesis of new substituted chromen[4,3-c]pyrazol-4-ones and their antioxidant activities
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A series of new coumarin derivatives 4 containing a 4-arylbut-3-en-2-one moiety were synthesized by condensation of 3-acetylcoumarin 1 with aryl aldehydes 2 in chloroform in the presence of piperidine. The interactions of 3-formyl-4-chlorocoumarin (3) with nitrogen-containg nucleophiles leading to the corresponding substituted chromen-[4,3- c]pyrazol-4-ones 5 are described. The structures of the obtained compounds were established on the basis of 1D NMR, 2D NMR and IR and further the compounds were evaluated for possible antioxidant activities. The coumarinic chalcone 4a has been found to be the most active (IC50 = 2.07 μM) in this study.
- Al-Ayed, Abdullah Sulaiman
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experimental part
p. 10292 - 10302
(2012/02/14)
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- A rapid access to new coumarinyl chalcone and substituted chromeno[4,3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities
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A series of new coumarin derivatives 4 containing a chalcone moiety were synthesized by condensation of 3-acetyl-4-hydroxycoumarin 1 with aryl or heteroaryl aldehydes 2 in the presence of piperidine in chloroform. The interaction of 3-formyl-4-chloro-coumarin 3 with nitrogen compound nucleophiles are described and lead to the corresponding substituted chromen[4,3-c] pyrazol-4-ones 5. The structures of the obtained compounds were established on the basis of IR|1D|2D NMR, while crystal structure of 3-acetyl-4-hydroxy coumarin 1 was determined using X-ray diffraction and further were evaluated for possible antibacterial and antioxidant activities. The coumarinic chalcone 4d has been found to be the most active (IC50 = 2.07 μM) in this study.
- Hamdi, Naceur,Fischmeister, Cedric,Puerta, M. Carmen,Valerga, Pedro
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experimental part
p. 522 - 530
(2012/05/04)
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- Synthesis and antimicrobial screening of 4H-2-acetyl-3-acetyamido furo[3,2-c] benzopyran 4-one, 11H-2,4-dimethyl-3,4-dihydro-3-amino-4-hydroxy- pyrimido [3,2-d]furo [3,2-c] benzopyran-11-one and 4H-2-acetyl-3-(3′- methyl-1′,2′,4′-triazol-4′-yl) furo[3,2-c] benzopyran 4-one
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A suspension of 4H-2-acctyl-3-amino furo [3,2-c] benzopyran 4-onc 5a-d in aqueous sodium hydroxide is treated with acetyl chloride to give 4H-2-acelyl-3-acclylamido furo[3,2-c] benzopyran 4-onc 6a-d. The compounds 6a-d and hydrazine hydrate in absolute alcohol is relluxed to give 11H-2,4-dimethyl-3,4-dihydro-3-amino-4-hydroxy-pyrimido[3,2-d] furo [3,2c]benzopyran-11-one 7a-d which in formic acid is relluxed for 5 hr to give 4H-2-acetyl-3-(3′-methyl-1′,2′,4′-triazol-4′-yl) furo[3.2-c]benzopyran 4-one 8a-d. The structures of all these compounds have been established on the basis of the spectral and analytical data. All compounds have showed good antimicrobial activity.
- Mulwad,Hegde
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scheme or table
p. 1558 - 1564
(2010/03/24)
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- 3,4-DISUBSTITUTED COUMARIN AND QUINOLONE COMPOUNDS
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The present invention relates to 3,4-disubstituted coumarin and quinolone derivatives and processes for their preparation. The invention also related to methods for treating infection of Hepatitis C virus by administering a 3,4-disubstituted coumarin or q
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- 3,4-Disubstituted coumarin and quinolone compounds
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The present invention relates to 3,4-disubstituted coumarin and quinolone derivatives and processes for their preparation. The invention also related to methods for treating infection of Hepatitis C virus by administering a 3,4-disubstituted coumarin or q
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Page/Page column 27-28
(2008/06/13)
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- Reactions of 4-chloro-3-formylcoumarin with arylhydrazines
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The interaction of 3-formyl-4-coumarin with arylhydrazine hydrochlorides in the presence of sodium acetate gave the corresponding 3-arylhydrazonomethyl-4- chlorocoumarin, and with phenylhydrazine, 4-bromo- and 4-chlorophenylhydrazine hydrochlorides in the
- Strakova,Petrova,Belyakov,Strakovs
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p. 1608 - 1616
(2007/10/03)
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- Synthesis of coumarin derivatives from 4-oxo-4H-1-benzopyran-3- carboxaldehyde via 3-(arylaminomethylene)chroman-2,4-dione
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K-10 Montmorillonite mediated condensation of aldehyde 1 with arylamine 2 affords chroman-2,4-dione 5 which gives tricoumarol 8 by acid hydrolysis, 4-arylamino-3-formylcoumarin 11 and 1-benzopyrano[4,3-b]quinoline 12 on heating with POCl3. 2000
- Bandyopadhyay, Chandrakanta,Ranabir Sur, Kumar,Patra, Ranjan,Sen, Arunabha
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p. 3583 - 3587
(2007/10/03)
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