Abstract
•Synthesis of new benzohydrazide based imines and thiazolidine-4-one derivatives and fully characterized by various spectroscopic techniques.•In vitro screening against alpha glucosidase and alpha amylase activities.•Identification of a new class of alpha glucosidase and alpha amylase activities.•Limited structure activity relationship was established to understand the contribution of different substituents.•In silico studies of most active compounds were performed to understand the binding interactions with enzyme.
Benzohydrazide based imine derivatives (1c-16c) and thiazolidine-4-one derivatives (1d-16d) were synthesized and characterized with different spectroscopic techniques i.e. HREI-MS, 1HNMR and 13CNMR. The synthesized analogs were examined for antidiabetic potential and hence evaluated against α-glucosidase and α-amylase enzyme. Benzohydrazide based imine derivatives showed outstanding α-glucosidase inhibition ranging from 5.60 ± 0.30 to 38.10 ± 0.30 µM when compared with acarbose (IC50 = 38.45 ± 0.80 µM). Compound 5c (IC50 = 5.60 ± 0.30 µM) has m/p-dihydroxyl groups at phenyl ring while compound 15c (IC50 = 7.30 ± 0.10 µM) has one p‑hydroxyl group present at phenyl ring were most potent in the imine series. Molecular docking study further support that hydrogen bonding is predominant. Thiazolidin-4-one derivatives (1d-16d) were screen against α-amylase enzyme and were found to show excellent potential with IC50 values ranging from 0.40 ± 0.05 to 22.11 ± 1.20 µM when compared with standard acarbose (IC50 = 0.91 ± 0.20 µM). The most potent analog in the series was 5d (IC50 = 0.40 ± 0.05 µM) when compared with standard. Molecular docking study was carried out for active site determination and to rationalize the activities of the active compounds.
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