Synthesis, characterization, In-silico and In-vitro investigation of sulfonamide based esters

•Three esters of sulfonamide were synthesized using ecofriendly environment.•Characterization was done through modern spectral and XRD techniques.•In silico DFT studies was used to compare experimental and theoretical parameters•In-vitro antimicrobial, antioxidant and enzyme inhibition potential were evaluated in order to explore their biological potential. In this study three new esters; methyl 4-((4-methoxyphenylsulfonamido)methyl)cyclohexane carboxylate; C16H23NO5S (I), ethyl 4-((4-methoxyphenylsulfonamido)methyl)cyclohexane carboxylate; C17H25NO5S (II) and isopropyl 4-((4-methoxyphenylsulfonamido)methyl)-cyclohexane carboxylate; C18H27NO5S (III) were synthesized in crystalline (I and II) and amorphous (III) form. Structural confirmation of these synthesized compounds was done using fourier transform infrared (FTIR), nuclear magnetic resonance (NMR), Mass and single crystal X-ray diffraction. The synthesized compounds were further subjected to their computational studies. All the synthesized compounds were screened for their in-vitro biological applications in term of antimicrobial, enzyme inhibition and free radical scavenging studies using spectrophotometric protocols. It was depicted from result that III gave higher antibacterial as well as antifungal activity comparable to the standard drugs. While, ester I showed profound antiradical scavenging activity against DPPH (2,2-diphenyl-1-picrylhydrazyl) radical. The compounds were also screened against esterase family; Acetylcholine esterase (AChE) and Butyrylcholine esterase (BChE) and it was found that I gave excellent inhibition activity towards AChE (91.1±0.7 %) as well as against BChE (84.1±0.9 %). In order to check the interactions of the compounds towards active sites of the respective enzyme, docking studies were carried out which confirmed that such compounds have good interaction to the amino acids residues on the active sites.