Three isomeric 4-[(n-bromophenyl)carbamoyl]butanoic acids ( n=2, 3 and 4) as DNA intercalator: Synthesis, physicochemical characterization, antimicrobial activity, antioxidant potential and in silico study

A series of three isomeric 4-[(n-bromophenyl)carbamoyl]butanoic acids ( n = 2, 3 and 4) were synthesized and their structures were confirmed by FTIR, NMR, MS, micro elemental analysis (CHN) and single crystal X-ray crystallography. Kinks are noted in the molecular structures of the n = 2 and n = 3 compounds, namely about the methylene-C-C(carbonyl) and N-C(phenyl) bonds; no such twist about the former bond is seen in the n = 4 molecule. In the molecular packing, supramolecular tapes are evident, being con-structed by orthogonally orientated O-H...O(carbonyl) and N-H...O(amide) hydrogen bonds. The synthe-sized compounds interact with salmon sperm DNA via an intercalative mode as confirmed by the UV-visible spectroscopic and viscometric techniques. The results of antimicrobial activity performed against five bacterial and two fungal strains show that these compounds have < 50% inhibition. Compound 3 has shown the maximum of 78% DPPH scavenging activity. SwissADME webserver was used for in silico study of the screened compounds and it was found that they obey the rules of drug-likeness and exhibit good potential for bioavailability. (c) 2022 Elsevier B.V. All rights reserved.

Automated summary

In this study, a series of isomeric 4-[(n-bromophenyl)carbamoyl]butanoic acids were synthesized and their structures were confirmed through various analytical techniques. The compounds showed antimicrobial activity against bacterial and fungal strains and exhibited good potential for bioavailability.