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

Abstract

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 constructed by orthogonally orientated O-H…O(carbonyl) and N-H…O(amide) hydrogen bonds. The synthesized 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.