Design, synthesis, characterization and antimicrobial evaluation of amide tagged 1,4-disubstituted 1,2,3-triazoles

Abstract

A series of amide tagged 1,4-disubstituted 1,2,3-triazole has been designed and synthesized in good yield through Cu (I) catalyzed click chemistry strategy. The synthesized triazoles were characterized by various spectral techniques like FT-IR, ¹H NMR, ¹³C NMR, and high-resolution mass spectrometery. The synthesized amide-tagged disubstituted triazoles were assessed for in vitro antimicrobial activity against two Gram-positive bacteria- Staphylococcus aureus, Bacillus subtilis; two Gram-negative bacteria- Escherichia coli, Klebsiella pneumonia and two fungi-Candida albicans, Aspergillus niger. Most of the synthesized compounds displayed good activity, among these, compound 6 m, 4-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide and compound 6t, 2-(4-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide with MIC values 0.020 and 0.017 µmol/mL respectively revealed appreciable efficacy against tested microbial strains. Further, molecular docking study also disclosed that docked compounds 6 m and 6t bound efficiently with the active site of receptor S. aureus DNA gyrase.

Graphical Abstract

Keywords:

• Amide tagged 1,2,3-triazole
• antimicrobial activity
• click chemistry
• molecular docking

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.