The biguanide–sulfonamide derivatives: synthesis, characterization and investigation of anticholinesterase inhibitory, antioxidant and DNA/BSA binding properties

Abstract

A number of new biguanidine-sulfonamide derivatives (1–16) were synthesized and their structures were characterized by spectroscopic and analytical methods. Crystal structures of the compounds 1, 4, 8, 10 and 14 were determined by single crystal X-ray diffraction studies. X-ray crystallographic data showed the π-electron delocalization through the biguanide units. The AChE and BChE cholinesterase inhibitor, DPPH antioxidant and DNA/BSA binding properties of the synthesized compounds were evaluated. Results of cholinesterase inhibitory properties have shown that the compounds containing electron-withdrawing (–F, –Cl) groups have higher AChE/BChE inhibitory and antioxidant activities. Compound 3 showed higher BChE inhibitory activity than tacrine with IC50 value of 28.4 µM. The compounds interact with DNA via minor groove binding mode. The compounds with a naphthyl group in its structure strongly binds with DNA/BSA biomolecules. Communicated by Ramaswamy H. Sarma