1516-58-1Relevant articles and documents
Preparation of aryl azides from aromatic amines in N-methyl-2-pyrrolidonium bisulfate
Hajipour, Abdol Reza,Mohammadsaleh, Fatemeh
, p. 451 - 455 (2011)
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Revisiting the thermal decomposition of five ortho-substituted phenyl azides by calorimetric techniques
Cardillo, Paolo,Gigante, Lucia,Lunghi, Angelo,Zanirato, Paolo
, p. 191 - 198 (2010)
The thermal decomposition (TD) of 2-azidophenylmethanol (1), 2-azidobenzenecarbaldehyde (2), 1-(2-azidophenyl)-1-ethanone (3), (2-azidophenyl)(phenyl)methanone (4) and 1-azido-2-nitrobenzene (5) was analysed by DSC, TG and C80 calorimetric techniques under both oxidative and non-oxidative conditions. The TD of these azides in solution is well known to give the corresponding benzoxazoles, generally in good yields, with the exception of azide 1. When both the outcomes from the solid phase and in 'solution phase' TD reactions combined with the results from EI-MS experiments were considered, sufficient information was available to estimate the azides intrinsic molecular reactivity (MIR).
Synthesis and antimicrobial potential of nitrofuran-triazole congeners
Kamal, Ahmed,Hussaini, S. M. Ali,Sucharitha, M. Lakshmi,Poornachandra,Sultana, Faria,Ganesh Kumar
, p. 9388 - 9397 (2015)
A series of 5-nitrofuran-triazole congeners were designed and synthesized by carrying out suitable structural modifications of the previously reported counterparts and were evaluated for their antimicrobial potential against both Gram-positive and Gram-ne
Design, synthesis & biological evaluation of ferulic acid-based small molecule inhibitors against tumor-associated carbonic anhydrase IX
Abid, Mohammad,Alajmi, Mohamed F.,Aneja, Babita,Daniliuc, Constantin G.,Hasan, Phool,Hassan, Md. Imtaiyaz,Hussain, Afzal,Khan, Parvez,Mohsin, Mohd.,Queen, Aarfa,Rizvi, M. Moshahid A.,Shamsi, Farheen
, (2020)
Carbonic anhydrase IX (CAIX) is an emerging drug target for hypoxia associated cancers. To identify potent and selective inhibitors of CAIX, a small library of ferulic acid (FA) derivatives bearing triazole moiety has been designed, synthesized and evaluated against different human CA isoforms (CAII, CAVA & CAIX). Though most of the compounds showed CAIX inhibition in the micromolar range, compound 7i selectively inhibits CAIX in the nanomolar range (IC50 = 24 nM). In silico analysis revealed binding of 7i with the catalytically important amino acid residues of CAIX. Further, cell-based studies indicate that 7i inhibits the activity of CAIX, decreases the epithelial to mesenchymal transitions, induces apoptosis, inhibits cell migration and colonization potential of cancer cells. Taken together, these results emphasized the use of 7i as a prospective pharmacological lead molecule in CAIX targeted anticancer therapeutics.
Synthesis, characterization, and pharmacological studies of ferrocene-1H-1,2,3-triazole hybrids
Haque, Ashanul,Hsieh, Ming-Fa,Hassan, Syed Imran,Haque Faizi, Md. Serajul,Saha, Anannya,Dege, Necmi,Rather, Jahangir Ahmad,Khan, Muhammad S.
, p. 536 - 545 (2017)
A series of ferrocene-1H-1,2,3-triazole hybrids namely 1-(4-nitrophenyl)-4-ferrocenyl-1H-1,2,3-triazole (1), 1-(4,4′-dinitro-2-biphenyl)-4-ferrocenyl-1H-1,2,3-triazole (2), 1-(3-chloro-4-fluorophenyl)-4-ferrocenyl-1H-1,2,3-triazole (3), 1-(4-bromophenyl)-
Synthesis, characterization and thermal behavior study of new 1,2,3-triazole derivatives containing 1,3,4-oxadiazole ring
Nahi, Riyadh J.,Kuwait, Zainab I.
, p. 416 - 422 (2019)
In this present work, a series of new 1-(substituted-phenyl)-1H-1,2,3-triazolyl-4-carboxylic acid derivatives was synthesized via copper (I) catalyzed azide-alkyne cycloaddition reaction. Since these synthesized 1,2,3-triazole compounds containing a carbo
1,2,3-Triazole-quinazolin-4(3H)-one conjugates: evolution of ergosterol inhibitor as anticandidal agent
Masood, Mir Mohammad,Irfan, Mohammad,Khan, Parvez,Alajmi, Mohamed F.,Hussain, Afzal,Garrison, Jered,Rehman, Md. Tabish,Abid, Mohammad
, p. 39611 - 39625 (2018)
The present study describes the synthesis of 1,2,3-triazole-quinazolinone conjugates (5a-q) from ethyl 4-oxo-3-(prop-2-ynyl)-3,4-dihydroquinazoline-2-carboxylate and phenyl azide/substituted phenyl azides employing Cu(i) catalysed Huisgen 1,3-dipolar cycloaddition. The corresponding acids (6a-q) were obtained by hydrolysis of esters (5a-q) to study the effect of these functionalities on the biological activity. All synthesized compounds were screened for in vitro anticandidal evaluation against Candia albicans, Candida glabrata and Candida tropicalis strains. The results indicated that compound 5n showed potent anticandidal activity with IC50 in the range of 8.4 to 14.6 μg mL?1. Hemolytic activity using human red blood cells (hRBCs) and cytotoxicity by MTT assay on human embryonic kidney (HEK-293) cells revealed the non-toxic nature of the selected compounds. Growth kinetic study with compound 5n showed its fungicidal nature as no significant growth of Candida cells was observed even after 24 h. Cellular ergosterol content was determined in the presence of different concentrations of 5n to measure the activity of lanosterol 14α-demethylase indirectly. The results showed significant disruption of the ergosterol biosynthetic pathway through inhibition of lanosterol 14α-demethylase activity supported by docking studies (PDB: 5v5z). Overall, this study demonstrates the anticandidal potential of 5n which can serve as the lead for further structural optimization and SAR studies.
Ionic liquids/[bmim][N3] mixtures: Promising media for the synthesis of aryl azides by SNAr
D'Anna, Francesca,Marullo, Salvatore,Noto, Renato
, p. 6224 - 6228 (2008)
(Formula Presented) The nucleophilic aromatic substitution of some activated aryl or heteroaryl halides has been performed in ionic liquid solution, using the 1-butyl-3-methylimidazolium azide as a nucleophile. The reaction course was studied varying the
A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: Design, synthesis, and biological evaluation
Wei, Gaofei,Luan, Weijing,Wang, Shuai,Cui, Shanshan,Li, Fengran,Liu, Yongxiang,Liu, Yang,Cheng, Maosheng
, p. 1507 - 1514 (2015)
A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(i) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds exhibited exc
Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids
Awolade, Paul,Cele, Nosipho,Kerru, Nagaraju,Singh, Parvesh
, p. 2201 - 2218 (2020/06/17)
Abstract: Antimicrobial resistance has become a significant threat to global public health, thus precipitating an exigent need for new drugs with improved therapeutic efficacy. In this regard, molecular hybridization is deemed as a viable strategy to afford multi-target-based drug candidates. Herein, we report a library of quinoline—1H-1,2,3-triazole molecular hybrids synthesized via copper(I)-catalyzed azide-alkyne [3 + 2] dipolar cycloaddition reaction (CuAAC). Antimicrobial evaluation identified compound 16 as the most active hybrid in the library with a broad-spectrum antibacterial activity at an MIC80 value of 75.39?μM against methicillin-resistant S. aureus, E. coli, A. baumannii, and multidrug-resistant K. pneumoniae. The compound also showed interesting antifungal profile against C. albicans and C. neoformans at an MIC80 value of 37.69 and 2.36?μM, respectively, superior to fluconazole. In vitro toxicity profiling revealed non-hemolytic activity against human red blood cells (hRBC) but partial cytotoxicity to human embryonic kidney cells (HEK293). Additionally, in silico studies predicted excellent drug-like properties and the importance of triazole ring in stabilizing the complexation with target proteins. Overall, these results present compound 16 as a promising scaffold on which other molecules can be modeled to deliver new antimicrobial agents with improved potency. Graphic abstract: [Figure not available: see fulltext.].
Synthesis, Characterization, and Cytotoxic Evaluation of New Triazole Derivatives of Osthol
Banday, J. A.,Chisti, H. N.,Rather, Z. K.
, p. 986 - 993 (2021/07/22)
Abstract: Osthol [7-methoxy-8-(3-methylbut-2-en-1-yl)chromen-2-one] isolated fromPrangos pabularia was used as a startingmaterial for the synthesis of its various derivatives via modifications of thelactone ring. The resulting compounds were fully charact