Synthesis of New Amide Linked Biphenoloxy 1,2,3-Triazoles as Antitubercular and Antimicrobial Agents

Abstract

New 1,2,3-triazoles bearing biphenoloxymethyl and acetanilido moieties (5a-5l) have been synthesized, starting from 4-phenylphenol (1) following click chemistry approach. The synthesized compounds have been thoroughly characterized by their ¹H NMR, ¹³C NMR and HRMS spectral data. These compounds were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H₃₇Rv and antimicrobial activity against pathogenic microbia. Among the screened compounds, 5a and 5i have displayed notable antitubercular activity with MIC 25 µg/mL. Compounds 5a, 5b, 5c, 5 g, 5i and 5 l have shown effective inhibition against most of tested pathogens. Molecular docking results of compounds 5a and 5i show the binding modes of the synthesized compounds into the active site of mycobacterial enoyl reductase. The synthesized compounds have also been analyzed for their ADME properties. By considering all these results, the present research work will offer a promising lead series for discovery of emerging potent antitubercular agents.

Keywords:

• Antimicrobial activity
• antitubercular activity
• click chemistry
• molecular docking
• study
• 1,2,3-triazole

Acknowledgments

Authors are grateful to Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad for antitubercular evaluation. One of the authors, STD is grateful to U.G.C., New Delhi, India for financial assistance in the form of NET Senior Research Fellowship. Authors also acknowledge Schrodinger Inc. for providing the academic license for GLIDE program to carry out the molecular docking studies.

Disclosure statement

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