Synthesis and biological evaluation of novel 2,4,5-triarylimidazole-1,2,3-triazole derivatives via click chemistry as α-glucosidase inhibitors.
A novel series of 2,4,5-triarylimidazole-1,2,3-triazole derivatives were synthesized via copper(I)-catalyzed azide-alkyne click chemistry, and evaluated for their α-glucosidase inhibitory activity. All tested compounds showed potent α-glucosidase inhibitory activity with IC50ranging from 15.16±0.18 to 48.15±0.37μM, in comparison to the standard drug, acarbose (IC50=817.38±6.27μM). Among all the tested compounds, 5j was found to be the most active compound with IC50value of 15.16±0.18μM and behaved as a noncompetitive inhibitor with a Kiof 14.78μM. In addition, molecular docking study was carried out to explore the binding interactions of these compounds with α-glucosidase enzyme.
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, PR China. Electronic address: wanggch123@163.com.
Guangcheng
G
Wang
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, PR China.
Zhiyun
Z
Peng
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, PR China.
Jing
J
Wang
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, PR China.
Juan
J
Li
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, PR China.
Xin
X
Li
D057930:Click Chemistry; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D062105:Molecular Docking Simulation; D012441:Saccharomyces cerevisiae / Q000737:chemistry / Q000201:enzymology / Q000378:metabolism; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000520:alpha-Glucosidases / Q000378:metabolism*
D065089:Glycoside Hydrolase Inhibitors; D007093:Imidazoles; D014230:Triazoles; D000520:alpha-Glucosidases
1,2,3-Triazole; 2,4,5-Triarylimidazole; Click chemistry; Enzyme kinetic study; Molecular docking; α-Glucosidase inhibitor