Synthesis, antioxidant and anti-diabetic potential of novel benzimidazole substituted coumarin-3-carboxamides

A series of benzimidazole tethered coumarin-3-carboxamide analogues were synthesised and screened for their antioxidant potential using DPPH and ABTS assay. And alpha-amylase inhibition potential also verified using DNSA method.The compound 10j with picoline substitution on the carboxamide linker emerged as most potent analogue for DPPH radical scavenging with IC50value 89.57 mu M in comparison with the stan-dard ascorbic acid (IC50 value 92.67 mu M) and the compound 10f with 3,5-dimethoxy phenyl substituted carboxamide linker exhibited strongest scavenging activity (IC50 = 93.45 mu M) against ABTS radical com-pared with the standard drug Trolox (IC50 = 96.24 mu M). However, all the compounds in the series showed moderate alpha-amylase inhibition and the compound 10f again emerged as best antidiabetic analogue in the series with IC50 67.52 mu M in comparison with metformin standard (IC50 = 54.13 mu M). Molecular docking study with the receptor protein alpha-amylase (PDB ID 4 x 9y) using Autodock Vina tool rationalised the results obtained.(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

A series of benzimidazole tethered coumarin-3-carboxamide analogues were synthesized and tested for their antioxidant potential using DPPH and ABTS assays. The compounds also demonstrated moderate alpha-amylase inhibition. Compound 10j showed the highest DPPH radical scavenging activity with an IC50 value of 89.57 μM, while compound 10f exhibited the strongest scavenging activity against ABTS radicals with an IC50 value of 93.45 μM. Compound 10f also emerged as the best antidiabetic analogue with an IC50 value of 67.52 μM.