Design, synthesis and molecular docking studies of 5-fluoro 1-aryl/alkyl sulfonyl benzimidazole derivatives for treatment of Parkinson’s disease

Abstract

Novel sulfonyl derivatives of 5-fluoro-substituted benzimidazole were synthesized and characterized by ¹H-NMR, ¹³C-NMR, ¹⁹F-NMR and mass spectrometry. Molecular docking study against monoamine oxidase B (MAO-B), responsible for Parkinson’s disease (PD), was performed. The binding energy and interactions with active amino acid residues in the binding site of newly synthesized derivatives, as well as conventional inhibitors (Selegiline and Rasagiline), were investigated and presented. According to the docking scores predicted by ADV (AutoDock vina) and AD (AutoDock), most of the synthesized derivatives have higher binding affinity toward MAO-B than the conventional inhibitors. This study shows that these fluoro-substituted benzimidazole derivatives can be developed into essential drugs for the treatment of PD. The antibacterial property of these compounds was investigated by disk diffusion test and minimum inhibitory concentration (MIC), against gram-negative and gram-positive bacteria. And the results were further verified by the bacteria kill test with respect to time. All the synthesized compounds demonstrated considerable antibacterial activity against both bacterial strains. Therefore, this work focuses on defining the efficiency of different types of sulfonyl derivatives of fluorinated benzimidazole in biomedical research for the treatment of PD highlighting their versatile biological properties.

Graphical Abstract

Keywords:

• Benzimidazole
• sulfonation
• antibacterial
• Parkinson
• docking

Acknowledgements

We would like to express special thanks to Prof. Swapan Mazumder (Professor, Tripura University, Tripura, India) for some ¹³C-NMR experiments required for the manuscript. This research was supported by Coochbehar Panchanan Barma University, West Bengal, India.

Author contribution

Subarna Roy: Conceptualization, investigation, formal analysis, and original draft preparation, Subhadeep Sen: Conceptualization, investigation, supervision, analysis, writing–review and editing, Samiran Saha: Investigation, formal analysis, Sandip Kumar Deb: Investigation, formal analysis, Bhagat Singh: Analysis, writing–review and editing, Goutam Biswas: Conceptualization, formal analysis, and writing–review and editing. All authors have read and agreed to the published version of the manuscript.

Data availability

All data generated or analyzed during this study are included in this published article (and its supporting information files).

Disclosure statement

The authors declare that they have no conflict of interests.

Additional information

Funding

The authors thank West Bengal DST Memo No. 403(Sanc.)/STBT-11012(25)/9/2021-ST SEC for support.