Synthesis of novel amides with antiradical capacity from 2-mercaptobenzimidazole and cinnamic acids: Evaluation through donor-acceptor maps and QSAR

The structures of thioethers I-III and the new amidic compounds 1(a-f)-3(a-f) derived from 2-mercaptobenzimidazole (MBZ) and cinnamic acids were confirmed by NMR and elemental analysis. Antioxidant activity was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH circle) radical scavenging assay and 2,2-azinobis (3-ethyl benzothiazoline-6-sulfonic acid) ABTS circle+ radical cation decolorization method. Besides, donor-acceptor maps (DAM) and electrophilicity were calculated using DFT/B3LYP method with a 6-311G(d,p) basis set. MBZ, I-III and (1a-3a) compounds showed higher activity in vitro antioxidant assays, confirming with in silico studies that they are the best candidates. The findings found in antiradical activity suggest that these compounds could be promising in the development of new antitumor and antimicrobial agents. QSAR Molecular properties and topological descriptors of the synthesized compounds 1(a-f)-3(a-f) were calculated. The QSAR model indicates that the size and molecular shape are relevant for the antiradical activity for this family of compounds. (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

The structures of thioethers I-III and the new amidic compounds 1(a-f)-3(a-f) were confirmed by NMR and elemental analysis. Antioxidant activity of these compounds were evaluated and showed promising results for the development of new antitumor and antimicrobial agents. QSAR model indicates that size and molecular shape are relevant for the antiradical activity of this compound family.