Synthesis, biological evaluation and molecular docking study of N-arylbenzo[d]oxazol-2-amines as potential α-glucosidase inhibitors.
A novel series of N-arylbenzo[d]oxazol-2-amines (4a-4m) were synthesized and evaluated for their α-glucosidase inhibitory activity. Compounds 4f-4i, 4k and 4m displayed potent inhibitory activity against α-glucosidase with IC50values in the range of 32.49±0.17-120.24±0.51μM as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of α-glucosidase with an IC50value of 32.49±0.17μM. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of α-glucosidase with a Kivalue of 31.33μM. Binding interaction of compound 4g with α-glucosidase was explored by molecular docking simulation.
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
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism*
D000588:Amines; D065089:Glycoside Hydrolase Inhibitors; D010080:Oxazoles; D000520:alpha-Glucosidases
Benzoxazole; Enzyme kinetic study; Molecular docking; Structure–activity relationship; α-Glucosidase inhibitor