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

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 pi-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 mu M. 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

Automated summary

A series of new biguanidine-sulfonamide derivatives were synthesized and their structures were characterized. Crystal structures of compounds 1, 4, 8, 10, and 14 were determined by X-ray diffraction. The compounds showed cholinesterase inhibitory, antioxidant, and DNA/BSA binding properties. Compounds with electron-withdrawing groups exhibited higher inhibitory and antioxidant activities, and compound 3 showed stronger BChE inhibitory activity than tacrine. The compounds interacted with DNA through minor groove binding, with naphthyl groups showing strong binding with DNA/BSA biomolecules.