637-81-0Relevant articles and documents
Synthesis, in Vitro Biological Evaluation, and Molecular Docking of New Triazoles as Potent Antifungal Agents
Li, Xiang,Liu, Chao,Tang, Sheng,Wu, Qiuye,Hu, Honggang,Zhao, Qingjie,Zou, Yan
, p. 42 - 49 (2016)
Based on the structure of the active site of CYP51 and the structure-activity relationships of azole antifungal compounds that we designed in a previous study, a series of 1-{1-[2-(substitutedbenzyloxy)ethyl]-1H-1,2,3-triazol-4-yl}-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ols (6a-n) were designed and synthesized utilizing copper-catalyzed azide-alkyne cycloaddition. Preliminary antifungal tests against eight human pathogenic fungi in vitro showed that all the title compounds exhibited excellent antifungal activities with a broad spectrum in vitro. Molecular docking results indicated that the interaction between the title compounds and CYP51 comprised π-π interactions, hydrophobic interactions, and the narrow hydrophobic cleft.
Thiacalix[4]arene derivatives containing multiple aromatic groups: High efficient extractants for organic dyes
Yang, Chuang,Wang, Zusheng,Guo, Hongyu,Jiao, Ziyu,Yang, Fafu
, p. 1383 - 1388 (2015)
Click reaction of alkynylthiacalix[4]arene with ethyl 2-azidoacetate, followed by ammonolysis with hydrazine hydrate and Schiff-base condensation with benzaldehyde or salicyic aldehyde, afforded two novel thiacalix[4]arene derivatives containing multiple aromatic groups in yields of 86% and 90%. Their complexation properties for four organic dyes were investigated by liquid-liquid extraction experiments, complexation UV-Vis spectra and mass spectrum. The highest extraction percentage was 97% for Neutral red. The UV-Vis spectra and ESI-MS spectrum indicated the 1:1 complexes in DMSO solution. The association constants were as high as 1 ～ 8×104 M-1. These complexation experiments showed that thiacalix[4]arene receptors possess excellent complexation capabilities for dyes. [Figure not available: see fulltext.]
Click synthesis and dye extraction properties of novel thiacalix[4]arene derivatives with triazolyl and hydrogen bonding groups
Guo, Hong-Yu,Yang, Fa-Fu,Jiao, Zi-Yu,Lin, Jian-Rong
, p. 450 - 452 (2013)
Using a click reaction between alkynylthiacalix[4]arene and ethyl 2-azidoacetate followed by an ammonolysis with ethanolamine, leucinol and hydrazine hydrate, respectively, three novel thiacalix[4]arene derivatives 4, 5 and 6 with triazolyl and hydrogen bonding groups (NH and OH) were synthesized in high yields. They exhibited excellent extraction capability for six anionic and cationic dyes. The flexible cavity, π-triazole rings and hydrogen bonding groups all play crucial roles in dye complexation.
Synthesis of near-infrared absorbing and fluorescing thiophene-fused BODIPY dyes with strong electron-donating groups and their application in dye-sensitised solar cells
Kubota, Yasuhiro,Kimura, Kosei,Jin, Jiye,Manseki, Kazuhiro,Funabiki, Kazumasa,Matsui, Masaki
, p. 1156 - 1165 (2019)
Thiophene-fused BODIPY dyes with two diethylaminophenyl groups as strong donors demonstrated near-infrared (NIR) absorption (λmax: 783-812 nm, ?: 119500-145900) and fluorescence (Fmax: 862-916 nm, Φf: 0.02-0.12) in dichloromethane. When applied to dye-sensitised solar cells, these dyes exhibited a panchromatic incident photon-to-current efficiency (IPCE) response from 400 to 850 nm, with the onset of the IPCE response at ～950 nm.
Synthesis and Bioactivity of Novel Trisubstituted Triazole Nucleosides
Wen, Yi-Ning,Zhang, Zhi-Feng,Liu, Ning-Ning,Xiang, Yu-Hong,Zhang, Zhuo-Yong,Andrei, Graciela,Snoeck, Robert,Schols, Dominique,Zhang, Qing-Shan,Wu, Qin-Pei
, p. 147 - 160 (2016)
A series of novel trisubstituted 1,2,3-triazole purine nucleosides were efficiently synthesized via Huisgen 1,3-dipolar cycloaddition in good yields. Bioactivity against cytomegalovirus (CMV) and varicella-zoster virus (VZV) in human embryonic lung cell cultures was evaluated and all compounds show low antiviral activity.
Synthesis of 1,2,3-triazoles linked into chains with other carbo- and heterocycles by a reaction between β-azolyl enamines and azides
Efimov, Ilya V.,Beliaev, Nikolai A.,Bakulev, Vasiliy A.,Beryozkina, Tetyana V.
, p. 167 - 172 (2018)
[Figure not available: see fulltext.] The reactions of β-azolyl enamines with azides proceeded under solvent-free conditions in the absence of base at 110°С by one of the possible routes, selectively forming 1,4-disubstituted 1,2,3-triazoles. The proposed reaction mechanism includes cycloaddition of the starting reagents, leading to 1,2,3-triazoline intermediates, followed by elimination of dimethylamine and the formation of aromatic triazole ring.
Metal ions recognition by 1,2,3-triazolium calix[4]arene esters synthesized via click chemistry
Li, Haibing,Zhan, Junyan,Chen, Mingliang,Tian, Demei,Zou, Zhilong
, p. 43 - 47 (2010)
Two triazole-modified calix[4]arene diesters were synthesized via Huisgen 1,3-dipolar cycloaddition between azides esters and alkynylcalixarenes. Their structures had been deduced from 1H NMR, element analysis and ESI-MS. Two-phase extraction experiments indicated that triazole-modified calix[4]arene diethylester 3a exhibited Cs+ selectivity. Springer Science+Business Media B.V. 2009.
Inhibition of acetylcholinesterase by coumarin-linked amino acids synthetized via triazole associated with molecule partition coefficient
De Sousa, Bianca L.,Leite, Jo?o P.V.,Mendes, Tiago A.O.,Varej?o, Eduardo V.V.,Chaves, Anna C.S.,da Silva, Júnio G.,Agrizzi, Ana P.,Ferreira, Priscila G.,Pilau, Eduardo J.,Silva, Evandro,dos Santos, Marcelo H.
, p. 652 - 664 (2021/02/16)
A previous study for the identification of acetylcholinesterase (AChE) inhibitors demonstrated that the hybrid between tyrosol, the 1,2,3-triazole nucleus, and the coumarin group, namely 7-({1-[2-(4-hydroxyphenyl)ethyl]-1H-1,2,3-triazol-4-yl}methoxy)-4-methyl-2H-chromen-2-one (10), has a high enzyme inhibitory activity. Here, we synthesized analogues of 10 via triazole with pharmacophoric groups represented by tyrosine, phenylalanine, tryptophan, and glycine in addition to evaluating the impact of coumarin-linked amino acids on AChE inhibition. We obtained eight triazoles, six of which are undescribed. In general, the presence of carboxylic acid decreased the inhibitory activity, while aromatic amino acids increased enzymatic inhibition compared to glycine. The derivative containing tyrosine, structurally most similar to 10, presented the lowest inhibition percentage, indicating that phenolic hydroxyl is not the preponderant factor for inhibition. Molecular docking was not enough to explain in vitro experiments. On the other hand, MlogP (logP calculated by the Moriguchi method) was related positively to enzymatic inhibition. To increase the hydrophobicity of the molecules, we tested the esterified triazole derivatives comparatively with the enzyme. The compound ethyl 2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)- 1H-1,2,3-triazol-1-yl)acetate (6) presented an increment of inhibitory activity of 46.97 ± 1.75% at 100 μmol L-1. We also associated the best activity with the lowest van der Waals volume and molar mass values.
Regioselective reduction of 1h-1,2,3-triazole diesters
Bendesky, Justin,Butler, Christopher R.,Schoffstall, Allen Milton
, (2021/09/24)
Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents
Tang, Kai-Wei,Hsu, Wen-Li,Chen, Cheng-Ru,Tsai, Ming-Hsien,Yen, Chia-Jung,Tseng, Chih-Hua
, p. 3589 - 3599 (2021/03/03)
Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds 7b-e, 8c-d, 10a-b and 10e inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid (10e) with the most potent inhibitory effect was chosen for further examination. The results revealed that compound 10e, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound 10e, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound 10e, is used as a promising lead compound for the development of a new treatment for fibrosis. This journal is
