Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

• Published in: Bioorganic Chemistry
• Main Author: Taha M.; Ismail N.H.; Javaid K.; Imran S.; Anouar E.H.; Wadood A.; Atia-Tul-Wahab; Ali M.; Khan K.M.; Saad S.M.; Rahim F.; Choudhary M.I.
• Format: Article
• Language: English
• Published: Academic Press Inc. 2015
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84942794211&doi=10.1016%2fj.bioorg.2015.09.001&partnerID=40&md5=ab9d824d62006e2a5510d5dd701506c3
• ISSN: 452068
• DOI: 10.1016/j.bioorg.2015.09.001

2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of νC=O, νN=C and νCH (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds. © 2015 Elsevier Inc. All rights reserved.