Sulfonamide tethered 1,4-disubstituted 1,2,3-triazoles: Synthesis and antibacterial evaluation

Abstract

A series of twenty one sulfonamide tethered 1,4-disubstituted 1,2,3-triazoles was synthesized in good yields through a facile expeditious click synthetic protocol involving Cu(I) mediated cyclization between terminal alkynes containing ester linkage and 4-azidobenzenesulfonamide. All the synthesized triazoles were characterized using FTIR,¹H NMR,¹³C NMR and HRMS techniques. Synthesized compounds were also evaluated for in vitro antibacterial activity against two Gram positive bacteria (Staphylococcus aureus, Bacillus subtilis) and two Gram negative bacteria (Klebsiella pneumoniae, Escherichia coli) by serial dilution method. In the series, compound 6 l, 3-(1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)propyl 4-bromobenzoate with Minimum Inhibitory Concentration (MIC) 0.0134 µmol/mL exhibited appreciable antibacterial activity against all bacterial strains comparable with standard drug Ciprofloxacin (MIC 0.0189 µmol/mL). Further, molecular docking study was also performed to gain insight for binding interactions with dihydropteroate synthase enzyme.

Graphical Abstract

Keywords:

• Click chemistry
• sulfonamide
• substituted 1,2,3-triazole
• antibacterial activity
• molecular docking

Acknowledgments

Funding as Senior Research Fellowship (SRF) from UGC is highly acknowledged. Authors also acknowledge APJ Abdul Kalam Central instrumentation laboratory, Guru Jambheshwar University of Science & Technology, Hisar, India, for NMR, IR and HRMS spectra of the synthesized compounds.

Declaration of interest

The authors declare there is no conflict of interest.