Synthesis, in vitro alpha-glucosidase inhibitory potential of benzimidazole bearing bis-Schiff bases and their molecular docking study

• Published in: Bioorganic Chemistry
• Main Author: Rahim F.; Zaman K.; Taha M.; Ullah H.; Ghufran M.; Wadood A.; Rehman W.; Uddin N.; Shah S.A.A.; Sajid M.; Nawaz F.; Khan K.M.
• Format: Article
• Language: English
• Published: Academic Press Inc. 2020
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85074862203&doi=10.1016%2fj.bioorg.2019.103394&partnerID=40&md5=553bb620ea57fe0c97e3cfb8c6bc9b7a

Voglibose and acarbose are distinguished α-glucosidase inhibitors used for controlling of diabetes mellitus. Unfortunately, these distinguished and clinically used inhibitors have also numerous side effects. Subsequently, there is still needed to develop safer therapy. Despite of a broad spectrum of biological importance of benzimidazole, it is occasionally evaluated for α-glucosidase activity. Current study deals with the synthesis and biological screening of benzimidazole bearing bis-Schiff bases (1–19) for their α-glucosidase inhibitory activity. All analogues exhibited excellent to good inhibitory potential (IC50 = 2.20 ± 0.1to 88.60 ± 1.70 µM) when compared with standard drug acarbose (IC50 = 38.45 ± 0.80 µM). A structure activity relationship has been established on the basis of electronic effects and position of different substituents present on phenyl ring. In order to rationalize the binding interactions of most active analogues with the active site of α-glucosidase enzyme, molecular docking study was conducted. © 2019 Elsevier Inc.