Sulfonamide Derived Esters: Synthesis, Characterization, Density Functional Theory and Biological Evaluation through Experimental and Theoretical Approach

Muhammad Danish,Muhammad Asam Raza,Ayesha Bibi,Nadia Noreen,Abdullah Mohamed Asiri,Muhammad Nadeem Arshad

doi:10.17344/acsi.2019.5720

Muhammad Danish, Muhammad Asam Raza + Show 4 more

Open Access

https://doi.org/10.17344/acsi.2019.5720

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Abstract

A series of new solid esters was synthesized by using greener chemistry strategy involving simple reaction of an alcohol with sulfonamide ligand. Characterization study of these methyl (1), ethyl (2) isopropyl (3) and n-butyl (4) ester of 4-((4-chlo-rophenylsulfonamido)methyl)cyclohexanecarboxylic acid was done by using FTIR, NMR mass spectrometry and X-ray crystallography. The compounds were optimized with Gaussian software according to basis set B3LYP/6-31G(d,p) and their different parameters related to structure were calculated. Furthermore, all compounds of the series were screened for their in vitro biological applications involving anti-bacterial (Chromohalobactor salixgens, Halomonas halofila, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Shiegella sonnei), anti-fungal (Aspergillus niger), anti-oxidant (DPPH scavenging activity) and enzyme inhibition (acetylcholine esterase and butyrylcholine esterase) study. Sulfonamide based esters were also docked against selected enzymes (AChE and BChE) using MOE software for their mode of binding. Results obtained from these biological evaluations showed that such compounds have potential against targeted activity.

Highlights

Infectious diseases due to bacteria or fungi are the major leading causes of morbidity all over the world.[1,2,3,4] The development of resistance in microbes against the present antibiotics is growing on a daily basis.[5]
Variety of carboxylate esters derived from sulfonamides are found to serve in the field of health by giving meritorious biological applications
The reaction gives water as by-product, the strategy is a type of green synthesis which is advantageous and environmentally friendly having no hazardous or harmful effects on the environment

Summary

Introduction

Infectious diseases due to bacteria or fungi are the major leading causes of morbidity all over the world.[1,2,3,4] The development of resistance (antibacterial) in microbes against the present antibiotics is growing on a daily basis.[5]. Researchers throughout the world are engaged in synthesizing and designing new drugs having widespread activity to overcome this issue.[6,7,8,9] Sulfonamides form the foundation for the first drugs mainly employed as preventive and chemotherapeutic agents against different ailments.[10] Sulfa drugs, having sulfonamide functionality, revolutionized the medicinal field due to their extensive biological activities.[11] Folic acid, an important compound for synthesis of bacterial nucleic acids, is inhibited by sulfonamides which leads to death of bacterial cells. Carboxylate ester formation implemented by reacting alcohol with carboxylic acid is such an example. Besides their applications in artificial flavoring of food and in perfume making,[12] esters of various compounds are found to show promising biological applications. Variety of carboxylate esters derived from sulfonamides are found to serve in the field of health by giving meritorious biological applications. As anti-microbial agents, esters of N-substituted sulfonamide are found to give anti-bacterial activity against four bacterial strains, i.e. Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli and Staphylococcus au-

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