88958-17-2Relevant academic research and scientific papers
Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents
Finiuk, Nataliya,Klyuchivska, Olha,Manko, Nazar,Matiychuk, Vasyl,Obushak, Mykola,Pokhodylo, Nazariy,Stoika, Rostyslav
, (2021/08/05)
Three series of novel 1H-1,2,3-triazole-4-carboxamides: 1-aryl-5-alkyl/aryl-1H-1,2,3-triazole-4-carboxamides, 1-aryl-5-amino-1H-1,2,3-triazole-4-carboxamides and 1,2,3-triazolo[1,5-a]quinazoline-3-carboxamides were synthesized via base-mediated click azide reactions. Compounds were evaluated for their antimicrobial activities against primary pathogens: Gram-positive and Gram-negative bacterial strains Escherichia coli, Klebsiella pneumonia, Acinetobacter baumannii, Pseudomonas aeruginosa, Staphylococcus aureus, as well as fungal strain Cryptococcus neoformans var. grubii and Candida albicans. Compounds exhibiting moderate to good activities were selected for SAR analysis. Several 5-methyl-1H-1,2,3-triazole-4-carboxamides 4d, 4l, 4r, showed potent antibacterial effect against S. aureus. On the contrary, 5-amino-1H-1,2,3-triazole-4-carboxamide 8b and [1,2,3]triazolo[1,5-a]quinazoline-3-carboxamide 9a were active against pathogenic yeast C. albicans. Thus, compound 4l under 1 μM demonstrated 50% growth inhibition against S. aureus. At the same concentration, the compound 9a killed approx. 40% of C. albicans cells. In general, these compounds demonstrated selective action and no significant impact on the viability of human keratinocytes of HaCaT line.
Synthesis of 1H-1,2,3-triazole-4-carbonitriles as building blocks for promising 2-(triazol-4-yl)-thieno[2,3-d]pyrimidine drug candidates
Sekh, Taras V.,Shyyka, Olga Y.,Pokhodylo, Nazariy T.,Obushak, Mykola D.
, p. 3175 - 3186 (2021/08/30)
A new synthetic route leading to functionalized 1H-1,2,3-triazole-4-carbonitriles has been developed. A set of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonitriles was obtained in high yields from readily available starting 1H-1,2,3-triazole-4-carboxylic aci
Picolinamide compound containing triazole or quinolinone structure and application of picolinamide compound
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Paragraph 0104; 0125-0126, (2020/01/12)
The invention provides a picolinamide compound containing a triazole or quinolinone structure and application of the picolinamide compound. According to a technical scheme in the invention, extensiveresearch is conducted on the picolinamide compound, and
A new 1,2,3-triazole and its rhodamine B derivatives as a fluorescence probe for mercury ions
Ding, Guohua,Feng, Huajie,He, Mengxiong,He, Wenying,Li, Jianling,Liao, Yuanhao,Liu, Rongqiang,Liu, Wei,Shi, Zaifeng,Wu, Luyong
, (2020/04/17)
A newly synthesized compound, 5-methyl-1-phenyl-1H-1,2,3-triazole-4- carboxylic acid (MPC) was analyzed for its quantum chemical parameters and theoretical spectrum by computational chemistry. The calculated spectrum was in accord with the experimental me
Discovery of novel pyrrolopyrimidine/pyrazolopyrimidine derivatives bearing 1,2,3-triazole moiety as c-Met kinase inhibitors
Wang, Linxiao,Liu, Xiaobo,Duan, Yongli,Li, Xiaojing,Zhao, Bingbing,Wang, Caolin,Xiao, Zhen,Zheng, Pengwu,Tang, Qidong,Zhu, Wufu
, p. 1301 - 1314 (2018/05/14)
Six series of pyrrolo[2,3-d]pyrimidine and pyrazolo[3,4-d]pyrimidine derivatives bearing 1,2,3-triazole moiety were designed and synthesized, and some bio-evaluation was also carried out. As a result, four points can be summarized: Firstly, some of compounds exhibited excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μm level. In particular, the most promising compound 16d showed equal activity to lead compound foretinib against A549, HepG2, and MCF-7 cell lines, with the IC50 values of 4.79?±?0.82, 2.03?±?0.39, and 2.90?±?0.43?μm, respectively. Secondly, the SARs and docking studies indicated that the in vitro antitumor activity of pyrrolo[2,3-d]pyrimidine derivatives bearing 1,2,3-triazole moiety was superior to the pyrazolo[3,4-d]pyrimidine derivatives bearing 1,2,3-triazole moiety. Thirdly, three selected compounds (16d, 18d, and 20d) were further evaluated for inhibitory activity against the c-Met kinase, and the 16d could inhibit the c-Met kinase selectively by experiments of enzyme-based selectivity. What is more, 16d could induce apoptosis of HepG2 cells and inhibitor the cell cycle of HepG2 on G2/M phase by acridine orange staining and cell cycle experiments, respectively.
Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety as c-Met kinase inhibitors
Tang, Qidong,Wang, Linxiao,Tu, Yayi,Zhu, Wufu,Luo, Rong,Tu, Qidong,Wang, Ping,Wu, Chunjiang,Gong, Ping,Zheng, Pengwu
, p. 1680 - 1684 (2016/07/27)
A series of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety were designed, synthesized, and evaluated for their c-Met kinase inhibitory activities and antiproliferative activities against 4 cancer cell lines (HT-29, A549, MCF-7, and PC-3) in vitro. Most compounds showed moderate to excellent potency, with the most promising analog 34 showing a c-Met IC50value of 1.68?nM. Structure–activity relationship studies indicated that electron-withdrawing groups (X?=?CF3, R1?=?F, R2?=?4-F) were required to decrease the higher electron density on the 5-atom linker to a proper degree to improve the inhibitory activity.
Discovery and biological evaluation of novel 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety as c-Met kinase inhibitors
Zhou, Shunguang,Liao, Huimin,Liu, Mingmei,Feng, Guobing,Fu, Baolin,Li, Ruijuan,Cheng, Maosheng,Zhao, Yanfang,Gong, Ping
, p. 6438 - 6452 (2015/02/02)
A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and five typical cancer cell lines (A549, H460, HT-29, MKN-45 and U87MG). Most compounds showed moderate to excellent antiproliferative activity. In this study, a promising compound 34, with a c-Met IC50 value of 1.04 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The SAR analyses indicated that compounds with halogen group, especially fluoro group, at 4-position on the phenyl ring (moiety B) have potent antitumor activity, and methylation on the 5-atom linker played an important role in the c-Met enzymatic activity.
Synthesis and anticancer activity evaluation of new 1,2,3-triazole-4- carboxamide derivatives
Pokhodylo, Nazariy,Shyyka, Olga,Matiychuk, Vasyl
, p. 2426 - 2438 (2014/05/06)
Anticancer screening of several novel 1,2,3-triazoles has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a multicomponent reaction which gave a wide
Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives
Pohodylo,Matiichuk,Obushak
, p. 275 - 279 (2014/04/17)
Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl) ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3- triazol-4-yl)-4,9-dihydro-3H-β-carbolines that can be transformed into β-carboline and tetrahydro-β-carboline derivatives.
Synthesis of polynuclear azoles linked through carbamate and urea bridges
Golobokova,Pokatilov,Proidakov,Kazantseva,Shevchenko,Vereshchagin,Kizhnyaev
experimental part, p. 566 - 574 (2012/07/02)
Polynuclear azoles linked through carbamate and urea fragments were synthesized by reactions of the corresponding azolecarboxylic acid azides with heterocyclic alcohols and amines. Pleiades Publishing, Ltd., 2012.
