- "Clicked" bivalent ligands containing curcumin and cholesterol as multifunctional Aβ oligomerization inhibitors: Design, synthesis, and biological characterization
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In our effort to develop multifunctional compounds that cotarget beta-amyloid oligomers (AβOs), cell membrane/lipid rafts (CM/LR), and oxidative stress, a series of bivalent multifunctional Aβ oligomerization inhibitors (BMAOIs) containing cholesterol and curcumin were designed, synthesized, and biologically characterized as potential treatments for Alzheimer's disease (AD). The in vitro assay results established that the length of spacer that links cholesterol and curcumin and the attaching position of the spacer on curcumin are important structural determinants for their biological activities. Among the BMAOIs tested, 14 with a 21-atom-spacer was identified to localize to the CM/LR of human neuroblastoma MC65 cells, to inhibit the formation of AβOs in MC65 cells, to protect cells from AβOs-induced cytotoxicity, and to retain antioxidant properties of curcumin. Furthermore, 14 was confirmed to have the potential to cross the blood-brain barrier (BBB) as demonstrated in a Caco-2 cell model. Collectively, these results strongly encourage further optimization of 14 as a new hit to develop more potent BMAOIs.
- Lenhart, James A.,Ling, Xiao,Gandhi, Ronak,Guo, Tai L.,Gerk, Phillip M.,Brunzell, Darlene H.,Zhang, Shijun
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Read Online
- Synthesis and incorporation of a caged tyrosine amino acid possessing a bioorthogonal handle
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Reversing a bioconjugation in a spatial and temporal fashion has widespread applications, especially toward targeted drug delivery. We report the synthesis and incorporation of an unnatural amino acid with an alkyne modified dimethoxy-ortho-nitrobenzyl ca
- Padilla, Marshall S.,Farley, Christopher A.,Chatkewitz, Lindsay E.,Young, Douglas D.
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- Supramolecular Assembly of Coronene Derivatives for Drug Delivery
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Possessing a small size and C3-symmetrical rigid backbone, a coronene derivative was synthesized from β-cyclodextrins and hexa-cata-hexabenzocoronene, and then a water-soluble and biocompatible nanographene/polysaccharide supramolecular assembl
- Yu, Jie,Chen, Yong,Zhang, Yu-Hui,Xu, Xun,Liu, Yu
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- Synthesis of Novel 1,2,3-Triazole-dihydro[3,2-c[chromenones as Acetylcholinesterase Inhibitors
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A novel series of 1,2,3-triazole-dihydro[3,2-c]chromenone derivatives were synthesized through an efficient three-step reaction starting from 4-hydroxybenzaldehyde. All the newly synthesized compounds were characterized by infrared and NMR spectroscopy as
- Saeedi, Mina,Ansari, Shirin,Mahdavi, Mohammad,Sabourian, Reyhaneh,Akbarzadeh, Tahmineh,Foroumadi, Alireza,Shafiee, Abbas
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- Efficient energy transfer between coronene-modified permethyl-β-cyclodextrins and porphyrin for light induced DNA cleavage
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A novel supramolecular assembly was constructed by the noncovalent complexation of hexa-cata-hexabenzocoronene modified permethyl-β-cyclodextrins with tetrasodium tetraphenylporphyrintetrasulfonate in water, exhibiting highly efficient excited energy tran
- Yu, Jie,Zhang, Ying-Ming,Li, Pei-Yu,Liu, Yu
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- Zinc(ii) triazole: Meso -arylsubstituted porphyrins for UV-visible chloride and bromide detection. Adsorption and catalytic degradation of malachite green dye
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Three new triazole meso-arylporphyrins (4a-c) were synthesized by the copper(i)-catalyzed azide alkyne cycloaddition (CuAAC) "click"reaction in high yield. The corresponding zinc(ii) coordination compounds (5a-c) have also been prepared. All 4a-c and 5a-c
- Aouadi, Ka?ss,Brahmi, Jihed,Guergueb, Mouhieddinne,Guerineau, Vincent,Loiseau, Frédérique,Najmudin, Shabir,Nasri, Habib,Nasri, Soumaya
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- A Facile Eco-Friendly One-Pot Five-Component Synthesis of Novel 1,2,3-Triazole-Linked Pentasubstituted 1,4-Dihydropyridines and their Biological and Photophysical Studies
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An eco-friendly one-pot five-component synthesis of novel 1,2,3-triazole-linked pentasubstituted 1,4-dihydropyridines under ultrasonic and microwave irradiation in polyethylene glycol (PEG) 400 is described. All newly synthesised compounds were evaluated
- Singh, Harjinder,Sindhu, Jayant,Khurana, Jitender M.,Sharma, Chetan,Aneja, Kamal R.
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- 1,2,3-Triazole tethered β-lactam-Chalcone bifunctional hybrids: Synthesis and anticancer evaluation
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The manuscript describes the synthesis of novel 1,2,3-triazole tethered β-lactam-chalcone bifunctional hybrids via click chemistry approach utilizing azide-alkyne cycloaddition reactions and their evaluation as anticancer agents against four human cancer
- Singh, Pardeep,Raj, Raghu,Kumar, Vipan,Mahajan, Mohinder P.,Bedi,Kaur, Tandeep,Saxena
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- Design and synthesis of 1,4-disubstituted 1,2,3-triazoles: Biological evaluation, in silico molecular docking and ADME screening
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In this study, propargyl compounds were synthesized from 4-hydroxybenzaldehyde and 3?methoxy-4-hydroxybenzaldehyde (2a-2b). As a result of click reactions of synthesized propargyl compounds (2a-b) with organic azides (4a-4e), carbonyl compounds (5a-5 h) h
- ?e?me, Mustafa,?zgeri?, Fatma Betül,?ahin, ?rfan,Güng?r, ?zge,Tümer, Ferhan
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- Discovery of new 1,4-disubstituted 1,2,3-triazoles: in silico ADME profiling, molecular docking and biological evaluation studies
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In this work, eight new 1,2,3-triazoles (6a–h) were synthesized from acetylenes’ “click” reaction with p-substituted azide derivatives. The structures of the compounds were characterized using standard analytical and spectroscopic methods (elemental analy
- ?e?me, Mustafa,?ahin, ?rfan,Tümer, Ferhan,Yüce, Neslihan
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- Synthesis, antiproliferative, docking and DFT studies of benzimidazole derivatives as EGFR inhibitors
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In the present work, new benzimidazole linked 1,2,3-triazole hybrids have been synthesized and screened for antiproliferative and EGFR kinase inhibitory activities.The structures of these hybrids were elucidated using IR, NMR, mass spectrometry and elemen
- Alam, Mohammad Mahboob,Alzahrani, Hessah Abdullah,Elhenawy, Ahmed A.,Malebari, Azizah M.,Nazreen, Syed
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- Just Add the Gold: Aggregation-Induced-Emission Properties of Alkynylphosphinegold(I) Complexes Functionalized with Phenylene-Terpyridine Subunits
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A series of organometallic complexes containing an alkynylphosphinegold(I) fragment and a phenylene-terpyridine moiety connected together by flexible linker have been prepared using the specially designed terpyridine ligands. The compounds were studied cr
- Abramova, Evgenia O.,Paderina, Aleksandra V.,Slavova, Sofia O.,Kostenko, Ekaterina A.,Eliseenkov, Eugene V.,Petrovskii, Stanislav K.,Gitlina, Anastasia Yu.,Boyarskiy, Vadim P.,Grachova, Elena V.
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supporting information
p. 18715 - 18725
(2021/12/09)
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- BCL-2 INHIBITOR
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Disclosed herein is a compound of Formula (I) for inhibiting both Bcl-2 wild type and mutated Bcl-2, in particular, Bcl-2 G101V and D103Y, and a method of using the compound disclosed herein for treating dysregulated apoptotic diseases.
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Paragraph 0982-0984
(2021/10/22)
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- Design, synthesis, characterization, and anticancer activity of a novel series of O-substituted chalcone derivatives
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A new series of O-substituted chalcone derivatives bearing an/a allyl-, prenyl- or propargyl-substituent at different positions of rings A and B and their derivatives as drug leads, was designed, synthesized, and characterized. The chalcone derivatives we
- Ngameni, Bathélémy,Cedric, Kamdoum,Mbaveng, Armelle T.,Erdo?an, Musa,Simo, Ingrid,Kuete, Victor,Da?tan, Arif
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supporting information
(2021/02/03)
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- Synthesis and structural characterization of novel O-substituted phenolic and chalcone derivatives with antioxidant activity
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A series of novel 4-O-alkyltriazolylphenolic derivatives is first synthesized with good to excellent yields via the click reaction of 3-methoxy-4-O-propargylbenzaldehyde or 3-allyl-4-O-propargylacetophenone and aromatic azide derivatives. Next, the chalco
- Ngameni, Bathélémy,Erdo?an, Musa,Kuete, Victor,Dalk?l??, Erdin,Ngadjui, Bonaventure T,Da?tan, Arif
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p. 159 - 165
(2020/07/03)
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- Preparation method and application of propyne aryl ether compound
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The invention particularly relates to a method for preparing propyne aryl ether compounds from aryl phenol, halogenated propyne and derivatives of the halogenated propyne, and belongs to the technical field of preparation of the propyne aryl ether compoun
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Paragraph 0079-0080
(2021/08/28)
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- Novel 1,2,3-triazolo phosphonate derivatives as potential antibacterial agents
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We describe the synthesis, characterization, and in vitro antibacterial evaluation of a library of novel compounds based on 1,2,3-triazolo phosphonate framework along with the evaluation of DNA gyrase inhibitory potential of a promising molecule in silico
- Telu, Jhonsee Rani,Kuntala, Naveen,Kankanala, Kavitha,Banothu, Venkanna,Pal, Sarbani,Anireddy, Jaya Shree
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p. 969 - 982
(2021/02/26)
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- Synthesis, characterization and UV–visible study of schiff base-acetylene functionalized organosilatrane receptor for the dual detection of Zn2+ and Co2+ ions
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The present article describes the synthesis of Schiff base-acetylene functionalized organosilatranes (6a–6e) and their characterization by 1H and 13C NMR spectroscopy and ESI-QTOF mass spectrometry. The UV–visible study of the organosilatrane 6a unveiled their high selectivity towards the recognition of Zn2+ and Co2+ ions without exhibiting any significant interference from other competitive metal ions. The calculated value of association constant with 6a for Zn2+ and Co2+ ions was 0.11 × 106 M?1 and 0.24 × 106 M?1 and the limit of detection was 0.28 × 10?6 M and 0.82 × 10?6 M respectively. Furthermore, DFT calculations were performed to get an insight into the interacting behaviour of sensor 6a towards Zn2+ and Co2+ ions.
- Devi, Anita,Diksha,Kaur, Jashan Deep,Priyanka,Saini, Anamika,Satija, Pinky,Singh, Gurjaspreet,Suman,Sushma
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- 1,2,3-triazole derivative: Synthesis, characterization, DFT, molecular docking study and antibacterial-antileishmanial activities
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In this study, 4-((1-(4-chlorobenzyl)-1H-1,2,3-triazole-4-yl)methoxy)-3-methoxybenzaldehyde (I) was synthesized and molecular structure of compound I was confirmed by FTIR and NMR (1H and 13C NMR) spectroscopic methods. The geometric
- ?elik, Fatih,Ustaba?, Re?at,Süleymano?lu, Nevin,Direkel, ?ahin,Güler, Halil ?brahim,ünver, Yasemin
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- Designing of chalcone functionalized 1,2,3-triazole allied bis-organosilanes as potent antioxidants and optical sensor for recognition of Sn2+ and Hg2+ ions
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This article presents the design, synthesis and characterization of a series of new acetylenic bis-chalcones (5a-5c) and chalcone functionalized 1,2,3-triazole allied bis-organosilanes (6a-6c) using aldol condensation followed by the Cu(I) catalyzed click
- Chowdhary, Kavita,Espinosa-Ruíz, Cristóbal,Esteban, Maria Angeles,González-Silvera, D.,Priyanka,Singh, Akshpreeet,Singh, Gurjaspreet,Singh, Jandeep,Sushma
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- Design, synthesis, antitrypanosomal activity, DNA/RNA binding and in vitro ADME profiling of novel imidazoline-substituted 2-arylbenzimidazoles
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Novel imidazoline benzimidazole derivatives containing diversely substituted phenoxy moieties were synthesized with the aim of evaluating their antitrypanosomal activity, DNA/RNA binding affinity and in vitro ADME properties. The presence of the diethylaminoethyl subunit in 18a–18c led to enhanced antitrypanosomal potency, particularly for 18a and 18c, which contain unsubstituted and methoxy-substituted phenoxy moieties. They were found to be > 2-fold more potent against African trypanosomes than nifurtimox. Fluorescence and CD spectroscopy, thermal denaturation assays and computational analysis indicated a preference of 18a–18c toward AT-rich DNA and their minor groove binding mode. Replacement of the amidine group with less basic and ionisable nitrogen-containing moieties failed to improve membrane permeability of the investigated compounds. Due to structural diversification, the compounds displayed a range of physico-chemical features resulting in variable in vitro ADME properties, leaving space for further optimization of the biological profiles.
- Kelly, John M.,Taylor, Martin C.,Baji?, Miroslav,Bokuli?, Ana,Jeli?, Dubravko,Ko?trun, Sanja,Krstulovi?, Luka,Popov, Andrea Bistrovi?,Rai?-Mali?, Silvana,Stojkovi?, Marijana Radi?,Zonji?, Iva
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- Design, synthesis and biological evaluation of new antioxidant and neuroprotective multitarget directed ligands able to block calcium channels
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We report herein the design, synthesis and biological evaluation of new antioxidant and neuroprotective multitarget directed ligands (MTDLs) able to block Ca2+ channels. New dialkyl 2,6-dimethyl-4-(4-(prop-2-yn-1-yloxy)phenyl)-1,4-dihydropyridi
- Angona, Irene Pachòn,Bonet, Alexandre,Borges, Fernanda,Daniel, Solene,Ismaili, Lhassane,Jó?wiak, Krzysztof,Maj, Maciej,Marco-Contelles, José,Martin, Helene,Refouvelet, Bernard,Silva, Tiago Barros,Wnorowski, Artur
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- Synthesis, characterization and biological evaluation of novel dihydropyranoindoles improving the anticancer effects of HDAC inhibitors
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The dihydropyranoindole scaffold was identified as a promising target for improving the anti-cancer activity of HDAC inhibitors from the preliminary screening of a library of compounds. A suitable methodology has been developed for the preparation of novel dihydropyranoindoles via the Hemetsberger indole synthesis using azido-phenylacrylates, derived from the reaction of corresponding alkynyl-benzaldehydes with methyl azidoacetate, followed by thermal cyclization in high boiling solvents. Anti-cancer activity of all the newly synthesized compounds was evaluated against the SH-SY5Y and Kelly neuroblastoma cells as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Biological studies showed that the tetracyclic systems had significant cytotoxic activity at higher concentration against the neuroblastoma cancer cells. More importantly, these systems, at the lower concentration, considerably enhanced the SAHA toxicity. In addition to that, the toxicity of designated systems on the healthy human cells was found to be significantly less than the cancer cells.
- Arndt, Greg M.,Bingul, Murat,Black, David StC,Cheung, Belamy B.,Kumar, Naresh,Marshall, Glenn M.
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- Kojic acid–natural product conjugates as mushroom tyrosinase inhibitors
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As part of our effort to develop potential tyrosinase inhibitors, we have conjugated the well-known tyrosinase inhibitor kojic acid (KA) with several phenolic natural products such as umbelliferone, sesamol, thymol, carvacrol, eugenol, isoeugenol, vanilli
- Ashooriha, Morteza,Emami, Saeed,Kardan, Mostafa,Khoshneviszadeh, Mahsima,Khoshneviszadeh, Mehdi,Rafiei, Alireza,Yazdian-Robati, Rezvan
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- New 1,2,3-triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation
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A new series of 1,2,3-triazole–(thio)barbituric acid hybrids 8a–n was designed and synthesized on the basis of potent pharmacophores with urease inhibitory activity. Therefore, these compounds were evaluated against Helicobacter pylori urease. The obtained result demonstrated that all the synthesized compounds, 8a–n, were more potent than the standard urease inhibitor, hydroxyurea. Moreover, among them, compounds 8a, 8c–e, 8g,h, and 8k,l exhibited higher urease inhibitory activities than the other standard inhibitor used: thiourea. Docking studies were performed with the synthesized compounds. Furthermore, molecular dynamic simulation of the most potent compounds, 8e and 8l, showed that these compounds interacted with the conserved residues Cys592 and His593, which belong to the active site flap and are essential for enzymatic activity. These interactions have two consequences: (a) blocking the movement of a flap at the entrance of the active site channel and (b) stabilizing the closed active site flap conformation, which significantly reduces the catalytic activity of urease. Calculation of the physicochemical and topological properties of the synthesized compounds 8a–n predicted that all these compounds can be orally active. The ADME prediction of compounds 8a–n was also performed.
- Asgari, Mohammad S.,Azizian, Homa,Nazari Montazer, Mohammad,Mohammadi-Khanaposhtani, Maryam,Asadi, Mehdi,Sepehri, Saghi,Ranjbar, Parviz R.,Rahimi, Rahmatollah,Biglar, Mahmood,Larijani, Bagher,Amanlou, Massoud,Mahdavi, Mohammad
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- Propargylated monocarbonyl curcumin analogues: synthesis, bioevaluation and molecular docking study
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In the current experimental study, we have synthesised new monocarbonyl curcumin analogues bearing propargyl ether moiety in their structure and evaluated for in vitro antifungal and radical scavenging activity. The antifungal activity was carried out aga
- Nagargoje, Amol A.,Akolkar, Satish V.,Subhedar, Dnyaneshwar D.,Shaikh, Mubarak H.,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 1902 - 1913
(2020/08/12)
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- Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: Cytotoxic effects on human cancer cells
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A new series of diverse 1,2,3-triazole-acridinedione/xanthenedione and 1,2-isoxazole-acridinedione/xanthenedione heterocyclic hybrids have been synthesized via 1,3-dipolar coupling reaction of N/O-substituted-acridinedione-alkyne or O-substituted-xanthene
- Albuquerque, Hélio,Almeida Paz, Filipe A.,Bachari, Khaldoun,Djemoui, Amar,Helguero, Luisa A.,Lahrech, Mokhtar Boualem,Lemouari, Najet,Mendes, Ricardo F.,Naouri, Abdelkader,Ouahrani, Mouhamad Ridha,Rocha, Djenisa H. A.,Silva, Artur M. S.,Talhi, Oualid
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- Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2 (TMS-EDTA)
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In the present work, novel 5-((1-benzyl-1,2,3-triazol-4-yl)methoxybenzylidene)-2-(arylamino)thiazol-4-one thiazolone incorporated triazole derivatives have been designed as tyrosinase inhibitors. The compounds were synthesized through click reaction in good yield. Moreover, the antityrosinas activity of the synthesized derivatives was evaluated. In the search for establishing a click copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction under strict conditions, in terms of a novel air-stable, a recyclable and efficient magnetic catalyst was planned for new triazole derivatives as a well-organized copper iodide supported on the functionalized Fe3O4@SiO2 core-shell (CuI/Fe3O4@SiO2(TMS-EDTA) nanoparticles). The engineered nanocatalyst synthesized for the first time and characterized by different methods, including FT-IR spectroscopy, XRD, FESEM, EDX, TEM, TGA, and BET analysis. The excellent catalytic performance in ethanol with high surface area (351.7 m2g?1) and short reaction time for diverse functional groups (120–200 min), no use of toxic solvents, reusability of the catalyst, and using eco-friendly conditions are the advantageous of this work. Moreover,the nanocatalyst can be used at least five times without any significant decrease in the yield of the reaction. The thiazolidine-triazole derivatives 9a, 9c, 9e, and 9 g showed promising tyrosinase inhibitory activity with IC50 values in the range of 5.90–9.81 μM. The compounds were found to be considerably more potent tyrosinase inhibitors than the reference inhibitor kojic acid (IC50 = 18.36 μM).
- Darroudi, Mahdieh,Ranjbar, Sara,Esfandiar, Mohammad,Khoshneviszadeh, Mahsima,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi,Sarrafi, Yaghoub
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- Design, synthesis and antibacterial activity evaluation of novel 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives
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In this paper, a novel series of 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives are synthesized in two steps. The first step involved Ugi multicomponent reaction of β-alanine, o-(propargyl)benzaldehyde and i
- Zarei, Samaneh,Komeili, Golzar,Bahadorikhalili, Saeed,Yahya-Meymandi, Azadeh,Karami-Zarandi, Morteza,Larijani, Bagher,Biglar, Mahmood,Sadat Ebrahimi, Seyed Esmaeil,Mahdavi, Mohammad
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p. 4254 - 4261
(2020/09/21)
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- Synthesis of coumarin-sulfonamide derivatives and determination of their cytotoxicity, carbonic anhydrase inhibitory and molecular docking studies
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Carbonic anhydrases isoforms CA IX, and XII are known to be highly expressed in various human tissues and malignancies. CA IX is a prominent target for especially colorectal cancers, because it is overexpressed in colorectal cancer and this overexpression
- Zengin Kurt, Belma,Sonmez, Fatih,Ozturk, Dilek,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
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- Anti-cancer potential of novel glycosylated 1,4-substituted triazolylchalcone derivatives
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A series of glycosylated 1,4-substituted triazolyl chalcone derivatives (8a-f and 14a-r) were synthesized in high yield using 1,3-cycloaddition (Click chemistry) of D-glucosyl azides with a variety of propargylated chalcone derivatives followed by de-O-ac
- Manna, Tapasi,Pal, Kunal,Jana, Kuladip,Misra, Anup Kumar
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supporting information
(2019/08/26)
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- Design, synthesis, structural characterization and in vitro evaluation of new 1,4-disubstituted-1,2,3-triazole derivatives against glioblastoma cells
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A new series of 1,4-disubstituted-1,2,3-triazole derivatives were synthesized through the copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (Click chemistry) and their inhibitory activities were evaluated against different human glioblastoma (GBM) c
- da Silva, Veronica D.,de Faria, Bruna M.,Colombo, Eduardo,Ascari, Lucas,Freitas, Gabriella P.A.,Flores, Leon? S.,Cordeiro, Yraima,Rom?o, Luciana,Buarque, Camilla D.
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- Design, synthesis,: In silico docking studies and biological evaluation of novel quinoxaline-hydrazide hydrazone-1,2,3-triazole hybrids as α-glucosidase inhibitors and antioxidants
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A new series of quinoxaline-hydrazidehydrazone-1,2,3-triazole hybrids, 14a-j, 15a-j and 16a-e, was designed, synthesized and screened for in vitro α-glucosidase and antioxidant activities. For the synthesis of the target compounds, quinoxaline hydrazides were condensed with benzaldehyde triazoles in the presence of AcOH (cat) in ethanol. The key step in the preparation of compounds 8a-j was the Cu(i)-catalyzed [3+2] cycloaddition reaction (CuAAC) with appropriate alkynes (6, 7) and azides, and 13a-j were prepared from simple aldehydes utilizing the same click reaction as the final step. Quinoxaline hydrazides (3, 3a) were synthesized from o-phenylenediamine and pyruvic acid via three-step reactions comprising cyclization, alkylation and hydrazidation. Among these hybrids, 14a (IC50 = 21.92 μg mL-1), 14b (IC50 = 22.32 μg mL-1), 14c (IC50 = 23.58 μg mL-1) and 15a (IC50 = 24.50 μg mL-1) showed good α-glucosidase inhibition compared with the standard acarbose (IC50 = 22.32 μg mL-1). Further, the scavenging abilities of the synthesized compounds as antioxidants were studied using the DPPH, H2O2, and NO methods; as per the obtained results, compounds 14a, 14b, 14c and 15a displayed good antioxidant activity. Docking studies of the active compounds and acarbose as a standard with α-glucosidase (PDB ID: 2ZEO) were performed to determine the molecular interactions between the inhibitors and the active site of the enzyme. Better binding energies of the active compounds than of the standard acarbose were observed. Therefore, our new hybrid molecules may be useful for further optimization in developing new lead molecules with both α-glucosidase inhibition and antioxidant activities.
- Settypalli, Triloknadh,Chunduri, Venkata Rao,Maddineni, Aruna Kumari,Begari, Nagaraju,Allagadda, Rajasekhar,Kotha, Peddanna,Chippada, Appa Rao
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p. 15435 - 15452
(2019/10/08)
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- A strategic approach to the synthesis of ferrocene appended chalcone linked triazole allied organosilatranes: Antibacterial, antifungal, antiparasitic and antioxidant studies
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A series of ferrocene appended chalcone allied triazole coupled organosilatranes (FCTSa 7–FCTSa 12) were synthesised with the aim of amalgamating the pharmacological action of the constituting moieties into a single molecular scaffold. All the synthesised
- Singh, Gurjaspreet,Arora, Aanchal,Kalra, Pooja,Maurya, Indresh Kumar,Ruizc, Cristobal Espinosa,Estebanc, M. Angeles,Sinha, Shweta,Goyal, Kapil,Sehgal, Rakesh
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p. 188 - 195
(2018/12/11)
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- Highly efficient and recyclable pre-catalysts based on mono- and dinuclear heteroleptic Cu(I) dithio- PPh3 complexes to produce variety of glycoconjugate triazoles
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Highly efficient and reusable pre-formed mono- and dinuclear heteroleptic copper(I) dithiocarbamate and dithiocarbimate complex based catalysts, [Cu(PPh3)2(L)] and [Cu2(PPh3)4(L)] (L = N-(4-methylpyri
- Singh, Avadhesh K.,Yadav, Chote Lal,Mishra, Kunj Bihari,Singh, Santosh K.,Gupta, Ajit N.,Tiwari, Vinod Kumar,Drew, Michael G.B.,Singh, Nanhai
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p. 152 - 163
(2019/04/25)
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- Click chemistry approach to characterize curcumin-protein interactions in vitro and in vivo
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Curcumin, a bis-α, β-unsaturated β-diketon dietary compound from turmeric, is among the most promising dietary compounds for preventing chronic diseases. Previous research has shown that curcumin is highly reactive toward protein thiols to form curcumin-p
- Yang, Haixia,Sukamtoh, Elvira,Du, Zheyuan,Wang, Weicang,Ando, Manami,Kwakwa, Yaa Nyamekye,Zhang, Jianan,Zhang, Guodong
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- First Anti-ToCV Activity Evaluation of Glucopyranoside Derivatives Containing a Dithioacetal Moiety through a Novel ToCVCP-Oriented Screening Method
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Tomato chlorosis virus (ToCV) is a newly reported plant virus that has rapidly spread to all parts of the world, resulting in a serious decline in tomato quality and yield due to the lack of effective control agents. In this study, the ToCV coat protein (
- Xie, Dandan,Zhang, Jian,Yang, Huanyu,Liu, Yuewen,Hu, Deyu,Song, Baoan
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p. 7243 - 7248
(2019/06/04)
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- New thiosemicarbazide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors: Design, synthesis, and biological evaluation
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A new series of thiosemicarbazide-1,2,3-triazole hybrids 10a-o has been synthesized, characterized by 1H NMR, 13C NMR, and screened for their in vitro α-glucosidase inhibitory activity. All of the synthesized compounds displayed excellent α-glucosidase inhibitory activity with IC50 values in the range of 75.0 ± 0.5 to 253.0 ± 0.5 μM, as compared to the standard drug acarbose (IC50 = 750.0 ± 1.5 μM). Among the synthesized compounds, compound 10h (IC50 = 75.0 ± 0.5)with 4-methoxy group at phenyl part of thiosemicarbazide moiety and 2,6-dichloro substituents at benzyl moiety was found to be the most potent compound. Kinetic analysis revealed that compound 10h is a competitive inhibitor for α-glucosidase. Docking study of compound 10h in the active site of α-glucosidase showed that this compound interacted with residues His239, His279, Glu304, Gly306, and Arg312.
- Bakherad, Zohreh,Mohammadi-Khanaposhtani, Maryam,Sadeghi-Aliabadi, Hojjat,Rezaei, Sepideh,Fassihi, Afshin,Bakherad, Mohammad,Rastegar, Hossein,Biglar, Mahmood,Saghaie, Lotfollah,Larijani, Bagher,Mahdavi, Mohammad
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p. 192 - 200
(2019/05/14)
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- A new series of Schiff base derivatives bearing 1,2,3-triazole: Design, synthesis, molecular docking, and α-glucosidase inhibition
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A series of new Schiff bases bearing 1,2,3-triazole 12a?o was designed, synthesized, and evaluated as α-glucosidase inhibitors. All the synthesized compounds showed promising inhibition against α-glucosidase and were more potent than the standard drug aca
- Nasli-Esfahani, Ensieh,Mohammadi-Khanaposhtani, Maryam,Rezaei, Sepideh,Sarrafi, Yaghoub,Sharafi, Zeinab,Samadi, Nasser,Faramarzi, Mohammad Ali,Bandarian, Fatemeh,Hamedifar, Haleh,Larijani, Bagher,Hajimiri, Mirhamed,Mahdavi, Mohammad
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- Dipropargyl substituted diphenylpyrimidines as dual inhibitors of monoamine oxidase and acetylcholinesterase
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Alzheimer's disease (AD) is a multifactorial neurological disorder involving complex pathogenesis. Single target directed drugs proved ineffective and since last few years' different pharmacological strategies including multi-targeting agents are being ex
- Kumar, Bhupinder,Kumar, Vijay,Prashar, Vikash,Saini, Suresh,Dwivedi, Ashish Ranjan,Bajaj, Beenu,Mehta, Devashish,Parkash, Jyoti,Kumar, Vinod
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p. 221 - 234
(2019/06/05)
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- Synthesis of novel perillyl-dihydropyrimidinone hybrids designed for antiproliferative activity
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A series of fifteen novel dihydropyrimidinone hybrid compounds were synthesized in good yields via a multicomponent reaction combined with the Huisgen reaction. The antiproliferative activity was investigated against nine tumor cell lines, and four hybrid
- Vendrusculo, Vinicius,De Souza, Vanessa P.,M. Fontoura, Luiz Ant?nio,M. D'Oca, Marcelo G.,Banzato, Thais P.,Monteiro, Paula A.,Pilli, Ronaldo A.,De Carvalho, Jo?o Ernesto,Russowsky, Dennis
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p. 1553 - 1564
(2018/10/02)
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- Synthesis and biological evaluation of chalcone-triazole hybrid derivatives as 15-LOX inhibitors
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An efficient aldol condensation/click reaction sequence is employed for the synthesis of chalcone-triazole-based derivatives in moderate to good yields. The ability of target compounds to inhibit 15-lipoxygenase enzyme was investigated and moderate to low inhibitory activities were observed for the synthesized compounds.
- Asadipour, Ali,Noushini, Saeedeh,Moghimi, Setareh,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Shabani, Shabnam,Firoozpour, Loghman,Foroumadi, Alireza
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- Efficient synthesis of α-substituted-α-arylmethyl phosphonates using trichloroacetimidate C–C coupling method
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A simple convenient protocol for the synthesis of diethyl α,α-diaryl methylphosphonate derivatives 5a-f, 6b-f, 7a-f and 8a-f, diethyl α-alkenyl α-aryl methylphosphonates 9a-d and 10a-d and α-(oxoalkyl) α-aryl methylphosphonate 11a-d and 12a-d is described. Trichloroacetimidates 3a-d were treated with activated arenes, styrene, allyltrimethylsilane or silylenol ethers C-nucleophiles in the presence TMSOTf to afford the desired products in good yields and short reaction time.
- Fathalla, Walid,Pazdera, Pavel,El-Rayes, Samir,Ali, Ibrahim.A.I.
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p. 1681 - 1691
(2018/03/01)
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- Anti-leishmanial click modifiable thiosemicarbazones: Design, synthesis, biological evaluation and in silico studies
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Leishmaniasis is a devastating tropical disease with limited therapeutic options. Depending on recently reported active anti-leishmanial compounds, we designed and synthesized a series of click modifiable 1,2,3-triazole and thiosemicarbazone hybrids. Most
- Temraz, Mohamed G.,Elzahhar, Perihan A.,El-Din A. Bekhit, Alaa,Bekhit, Adnan A.,Labib, Hala F.,Belal, Ahmed S.F.
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p. 585 - 600
(2018/04/17)
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- blue calyx a su-glucose derivative and its preparation method and application
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The invention relates to glucose derivatives of glaucocalyxin A. The glucose derivatives have a structure represented by a formula I or a formula II, wherein R1 represents hydrogen or methoxyl, R2 represents hydrogen or acetyl, and n represents 0 or 1. Th
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Paragraph 0083; 0084; 0085; 0086
(2017/08/25)
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- Quinazoline derivatives as selective CYP1B1 inhibitors
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CYP1B1 is implicated to have a role in the development of breast, ovarian, renal, skin and lung carcinomas. It has been suggested that identification of potent and specific CYP1B1 inhibitors can lead to a novel treatment of cancer. Flavonoids have a compact rigid skeleton which fit precisely within the binding cavity of CYP1B1. Systematic isosteric replacement of flavonoid ‘O’ atom with ‘N’ atom led to the prediction that a ‘quinazoline’ scaffold could be the basis for designing potential CYP1B1 inhibitors. A total of 20 quinazoline analogs were synthesized and screened for CYP1B1 and CYP1A1 inhibition in Sacchrosomes. IC50 determinations of six compounds with capability of inhibiting CYP1B1 identified quinazolines 5c and 5h as the best candidates for CYP1B1 inhibition, with IC50 values in the nM range. Further selectivity studies with homologous CYPs, belonging to the CYP1, CYP2 and CYP3 family of enzymes, showed that the compounds are likely to be free from critical drug-drug interaction liability. Molecular modelling studies were performed to rationalize the observed enzymatic inhibitions. Further biological studies in live yeast and human cells, harboring CYP1A1 and CYP1B1 enzymes, have illustrated the most potent compounds' cellular permeability and capability of potently inhibiting CYP1B1 enzyme expressed within live cells.
- Mohd Siddique, Mohd Usman,McCann, Glen J.P.,Sonawane, Vinay R.,Horley, Neill,Gatchie, Linda,Joshi, Prashant,Bharate, Sandip B.,Jayaprakash, Venkatesan,Sinha, Barij N.,Chaudhuri, Bhabatosh
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p. 320 - 327
(2017/03/10)
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- Curcuminoid-BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
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Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluo
- Weiss, Henning,Reichel, Jeannine,G?rls, Helmar,Schneider, Kilian Rolf Anton,Micheel, Mathias,Pr?hl, Michael,Gottschaldt, Michael,Dietzek, Benjamin,Weigand, Wolfgang
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supporting information
p. 2264 - 2272
(2017/11/16)
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- Click inspired synthesis of triazole-linked vanillin glycoconjugates
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The 1,3-dipolar cycloaddition of deoxy-azido sugars 1 with alkyne derivatives of p-vanillin, 3-methoxy-4-(prop-2-ynyloxy)benzaldehyde (2) and 2-methoxy-1-(prop-2-ynyloxy)-4-((prop-2-ynyloxy)methyl)benzene) (4) to afford regioselective triazole-linked vanillinglycoconjugates 5 and 6 was investigated in the presence of CuI/DIPEA in dichloromethane. All the developed glycoconjugates were characterized on the basis of IR, NMR, and MS. [Figure not available: see fulltext.]
- Dwivedi, Pratibha,Mishra, Kunj B.,Pritika,Mishra, Bhuwan B.,Tiwari, Vinod K.
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- Cu2O spheres as an efficient source of catalytic Cu(I) species for performing azide-alkyne click reactions
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We report herein the high yield synthesis of Cu2O spheres displaying well-defined shapes and monodisperse sizes that could be employed as the source of highly catalytic active Cu(I) species towards click reactions between several of alkynes and azides to produce a variety of 1,2,3-triazoles under ligand-free and ambient conditions (in an open reactor). The utilization of Cu2O spheres enabled superior performance as compared to a conventional protocol in which CuSO4is employed in combination with sodium ascorbate as the catalyst system. In addition, the compounds were obtained in synthetically useful yields, and seven of them have not been previously reported. We believe the results reported herein shed new insights into the optimization of activity and versatility of click reactions towards the synthesis of target molecules in environmentally friendly conditions.
- Rodrigues, Thenner S.,da Silva, Anderson G.M.,de Oliveira, Lucas C.,da Silva, Adalberto M.,Teixeira, Róbson R.,Camargo, Pedro H.C.
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supporting information
p. 590 - 595
(2017/01/16)
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- Synthesis and molecular docking studies of novel 2-phenyl-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}oxazol-5(4H)-one derivatives
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2-Phenyl-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}oxazol-5(4H)-one derivatives were synthesized by click chemistry reactions. Exploration of molecular interaction of the obtained compounds, performed through molecular docking studies with
- Sathish Kumar,Anantha Lakshmi
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p. 1057 - 1063
(2017/06/29)
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- Design and synthesis of 1,2,3-triazole-etodolac hybrids as potent anticancer molecules
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A series of novel 1,2,3-triazole-etodolac hybrids (6a-l) were designed and synthesized as potent anti-cancer molecules. The synthesis strongly relied on Huisgen's 1,3-dipolar cycloaddition between etodolac azide 3 and substituted terminal alkynes 5a-l. Th
- Kummari, Bhaskar,Polkam, Naveen,Ramesh, Perla,Anantaraju, Hasithashilpa,Yogeeswari, Perumal,Anireddy, Jaya Shree,Guggilapu, Sravanthi Devi,Babu, Bathini Nagendra
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p. 23680 - 23686
(2017/07/07)
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- Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities
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The present study was carried out in an attempt to synthesize a new class of antimicrobial and antiplasmodial agents by copper catalyzed click chemistry to afford 25 compounds 10-14(a-e) of 1,4-disubstituted-1,2,3-triazole derivatives of chalcones and flavones. The structures of the newly synthesized compounds were established by elemental analysis, IR, 1H NMR, 13C NMR and Mass spectral data. The newly synthesized compounds were evaluated for their antibacterial activity against Gram positive bacteria (Staphylococcus aureus, Enterococcus faecalis), Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Shigella boydii, Klebsiella pneumoniae) and antifungal activity against (Candida albicans, Candida tropicalis, Candida parapsilosis, Cryptococcus neoformans, Dermatophyte) as well as molds (Aspergillus niger, Aspergillus fumigatus). The antiplasmodial and cytotoxic activities of these compounds were also evaluated against human malaria parasite Plasmodium falciparum strain 3D7 and human hepato-cellular carcinoma cells (Huh-7), respectively. Compounds 10a, 10c, 10d, 12c and 14e showed promising antibacterial activity while compounds 10e, 11d, 11e, 12c, 13a, 13b, 13e, 14a and 14d showed good antifungal activity as compared to the corresponding standard drugs. Compound 10b was found to be the most active against Plasmodium falciparum while the remaining compounds showed moderate to weak antiplasmodial activity. However, cytotoxic activities of all compounds were found ineffective against Huh-7 cells.
- Kant, Rama,Kumar, Dharmendra,Agarwal, Drishti,Gupta, Rinkoo Devi,Tilak, Ragini,Awasthi, Satish Kumar,Agarwal, Alka
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- 1. - 2, 3 - triazole - flavonoid compound matrine ternary the yoke unites and use
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The invention discloses a 1,2,3-triazole-flavonoid compound-sophocarpidine ternary conjugate and the use. The 1,2,3-triazole-flavonoid compound-sophocarpidine ternary conjugate has a structure as shown in the specification. The 1,2,3-triazole-flavonoid co
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Paragraph 0059; 0060
(2016/10/09)
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- Bivalent multifunctional ligands targeting Aβ oligomers as treatment for Alzheimer's disease
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Bivalent multifunctional Aβ oligomerization inhibitors (BMAOIs) that target multiple risk factors involved in Alzheimer's disease are provided. The BMAOIs are useful for the treatment and/or prevention of Alzheimer's disease, as well as for diagnostic ima
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Page/Page column 23
(2016/03/12)
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- Synthesis of novel symmetrical 1,4-disubstituted 1,2,3-bistriazole derivatives via 'click chemistry' and their biological evaluation
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A series of symmetric bis-1,2,3-triazole compounds 2-5(a-f) were synthesized as potential antioxidant agents via click chemistry. Their structures were confirmed by 1H-NMR and 13C-NMR. All of the synthesized compounds were subjected
- Dü?dü, Esra,ünlüer, Dilek,?elik, Fatih,Sancak, Kemal,Karao?lu, ?engül Alpay,?zel, Arzu
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