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

Keywords:

• Biguanidine–sulfonamide
• cholinesterase inhibition
• antioxidant
• DNA/BSA binding

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Data availability statement

Data will be made available on request.

Additional information

Funding

We are grateful to Kahramanmaras Sutcu Imam University Research Unit (Project Number: 2019/6-22 M and 2020/6-14D) for the financial support. Furthermore, we would like to thank the Higher Education Council Research Board (YÖK 100/2000 PhD. Scholarship Priority Areas Program field: 02.01.02 “Molecular Pharmacology and Pharmaceutical Research”) for granting the Scholarship (to Özge Güngör). Scientific Research Projects Coordination Unit of Kahramanmaras Sutcu Imam University for post doc (DOSAP) Scholarship (Özge Güngör).