35523-91-2Relevant academic research and scientific papers
Design, synthesis and biological evaluation of potential anti-AD hybrids with monoamine oxidase B inhibitory and iron-chelating effects
Guo, Jianan,Mi, Zhisheng,Jiang, Xiaoying,Zhang, Changjun,Guo, Zili,Li, Linzi,Gu, Jinping,Zhou, Tao,Bai, Renren,Xie, Yuanyuan
, (2020/12/29)
A series of active hybrids combining 3-hydroxypyridin-4(1H)-one and coumarin pharmacophores were designed and synthesized as potential agents for the treatment of Alzheimer's disease (AD). All the compounds exhibited excellent iron-chelating activities (p
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
Vagish, Channa Basappa,Kumara, Karthik,Vivek, Hamse Kameshwar,Bharath, Srinivasan,Lokanath, Neratur Krishnappagowda,Ajay Kumar, Kariyappa
, (2021/02/05)
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.
Synthesis and Biological Evaluation of New Ibuprofen-1,3,4-oxadiazole-1,2,3-triazole Hybrids
Rayam, Parsharamulu,Polkam, Naveen,Kummari, Bhaskar,Banothu, Venkanna,Gandamalla, Durgaiah,Yellu, Narsimha Reddy,Anireddy, Jaya Shree
, p. 296 - 305 (2018/12/13)
A new hybrid polydentate template comprising distinctive pharmacophoric groups, namely, ibuprofen, 1,3,4-oxadiazole, and 1,2,3-triazole linked through a thioether bridge was achieved by one-pot synthesis by exploring multicomponent Cu-catalyzed “click chemistry” approach. The target structures were characterized by NMR, IR, and LC-Mass. The X-ray analysis of 2-(1-(4-isobutylphenyl)ethyl)-5-(((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-1,3,4-oxadiazole (8a) confirmed the assigned structure. The in vitro antibacterial and anticancer activity of these compounds revealed that 2-(1-(4-isobutylphenyl)ethyl)-5-(((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)thio)-1,3,4-oxadiazole (8b) demonstrated more potent antibacterial activity against Gram-negative strains (Escherichia coli and Pseudomonas aeruginosa) and 2-(((1-(2,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-5-(1-(4 isobutylphenyl)ethyl)-1,3,4-oxadiazole (8e) exhibited anticancer activity with IC50 of 27.50 and 31.03?μg/mL against HeLa and MCF-7 cell lines, respectively.
Triazole-Based Inhibitors of the Wnt/β-Catenin Signaling Pathway Improve Glucose and Lipid Metabolisms in Diet-Induced Obese Mice
Obianom, Obinna N.,Ai, Yong,Li, Yingjun,Yang, Wei,Guo, Dong,Yang, Hong,Sakamuru, Srilatha,Xia, Menghang,Xue, Fengtian,Shu, Yan
, p. 727 - 741 (2019/01/21)
Wnt/β-catenin signaling pathway is implicated in the etiology and progression of metabolic disorders. Although lines of genetic evidence suggest that blockage of this pathway yields favorable outcomes in treating such ailments, few inhibitors have been used to validate the promising genetic findings. Here, we synthesized and characterized a novel class of triazole-based Wnt/β-catenin signaling inhibitors and assessed their effects on energy metabolism. One of the top inhibitors, compound 3a, promoted Axin stabilization, which led to the proteasome degradation of β-catenin and subsequent inhibition of the Wnt/β-catenin signaling in cells. Treatment of hepatocytes and high fat diet-fed mice with compound 3a resulted in significantly decreased hepatic lipid accumulation. Moreover, compound 3a improved glucose tolerance of high fat diet-fed mice without noticeable toxicity, while downregulating the genes involved in the glucose and fatty acid anabolisms. The new inhibitors are expected to be further developed for the treatment of metabolic disorders.
Design, combinatorial synthesis and biological evaluations of novel 3-amino-1'-((1-aryl-1H-1,2,3-triazol-5-yl)methyl)-2'-oxospiro[benzo[a] pyrano[2,3-c]phenazine-1,3'-indoline]-2-carbonitrile antitumor hybrid molecules
Lu, Yuanyuan,Wang, Linlin,Wang, Xiaobing,Xi, Tao,Liao, Jianmin,Wang, Zhixiang,Jiang, Feng
, p. 125 - 141 (2017/04/26)
A combinatorial chemical library of fifty-nine novel 3-amino-1'-((1-aryl-1H-1,2,3-triazol-5-yl)methyl)-2'-oxospiro[benzo[a]pyrano[2,3-c]phenazine-1,3'-indoline]-2-carbonitrile, designed as hybrid molecules of phenazine, pyran, indole and 1,2,3-triazole pharmacophores, were constructed in this study. Cytotoxic evaluation indicated that some compounds exhibited moderate cytotoxicity against HCT116, MCF7, HepG2 and A549 cancer cell lines in vitro, in which compound 36 was found to have best antiproliferative activity against the A549 cancer cell line with IC50 value of 5.4 μM. All compounds had low or no effect against L02 and HUVEC non-cancer cell lines. Compound 36 was further confirmed to mainly locate mitochondria in A549 cancer cells via laser-scanning confocal microscopy. Moreover, compound 36 was proved to increase ROS production and induce cell cycle arrest in S phase. Western blot analysis illustrated Bax/Bcl-2 ratio was increased at dose-dependent manner, and both cleaved caspase-3 and cleaved caspase-9 was enhanced by treated with compound 36. All the above evidences in vitro indicated that compound 36 might induce the apoptosis of A549 cancer cells via a mitochondria-dependent pathway.
One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
Zhao, Fen,Chen, Zhen,Xie, Kai,Yang, Rui,Jiang, Yu-Bo
, p. 109 - 113 (2016/01/25)
A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.
New syntheses of DNA adducts from methylated anilines present in tobacco smoke
Branco, Paula S.,Antunes, Alexandra M. M.,Marques, M. Matilde,Chiarelli, M. Paul,Lobo, Ana M.,Prabhakar, Sundaresan
, p. 1223 - 1233 (2007/10/03)
A new synthetic pathway for the formation of deoxyguanosine- monoarylamine adducts is described, involving the generation and use of arylnitrenes as electrophilic synthons. Photolysis of aryl azides, the most common method for generating arylnitrenes, was
