Synthesis, characterization and biological activities of sulfonamide tagged 1,2,3-triazoles

Abstract

The present paper elicits a marvelous synthesis of a series of sulfonamide containing 1,4-disubstituted 1,2,3-triazoles through click reaction of terminal alkynes with aromatic azides. The synthesized triazoles were characterized by FTIR, ¹H NMR,¹³C NMR and HRMS techniques. Further, the structures of synthesized compounds 6u (CCDC 1954932) and 6z₃ (CCDC 1954931) were also confirmed by X-ray crystallography. The synthesized triazoles were evaluated for in vitro antibacterial activity against S. aureus, B.subtilis, E. coli and K. pneumoniae by serial dilution method. Among the series, compound 4-bromo-N-(2-(1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl)propan-2-yl)benzenesulfonamide, 6z₄ (MIC = 0.025 µM/mL) and 4-bromo-N-(2-(1-(naphthalen-1-yl)-1H-1,2,3-triazol-4-yl)propan-2-yl)benzenesulfonamide 6z₆ (MIC = 0.027 µM/mL) exhibited the appreciable antibacterial activity against Staphylococcus aureus and Bacillus subtilis. Further, the molecular docking studies of above potent analogs with dihydropteroate synthase was performed to have an insight for binding interactions. Synthesized molecules were also explored for antioxidant activity, reflecting compound 6m as better radical scavenging agent with IC₅₀ value of 1.96 µM/mL.

Graphical Abstract

Keywords:

• Biological evaluation
• click chemistry
• crystal structure
• sulfonamide
• 123-triazole

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

Authors are highly thankful to the Council of Scientific and Industrial Research (CSIR) for financial assistance.