ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

[DIPEA][OAc]-Mediated and Ultrasound-Assisted Synthesis of Isoniazid Based 1,2,3-Triazoles as Antitubercular and Antioxidant Agents

Madiha M. Siddiqui, Amol A. Nagargoje, Mubarak H. Shaikh, Dipti D. More, Rashiqua A. Siddiqui, Dharmarajan Sriram, Vijay M. Khedkar, and Bapurao B. Shingate

Department of Chemistry, Dr. Babasaheb Ambedkar, Marathwada University, Chhatarpati Sambhajinagar, India

E-mail: bapushingate@gmail.com

Received: 22 July 2025  Accepted: 22 December 2025

Abstract:

The functional modification of isoniazid has always been a hotspot in the drug development. In this paper, we have described ultrasound-assisted and [DIPEA][OAc-mediated synthesis of isoniazid based 1,2,3-triazole derivatives via click chemistry approach in excellent yields (upto 95%) and short reaction time (30 min). The synthesized derivatives were evaluated for their in vitro antitubercular activity against the Mycobacterium tuberculosis H37Rv strain. Notably, the compound 12i exhibited remarkable activity with lower MIC value 1.56 µg/mL. All the synthesised compounds were screened for their antioxidant potential and showed comparable IC₅₀ values ranging from 10.01 ± 0.21 to 15.04 ± 0.01 µg/mL with the the standard, ascorbic acid. Molecular docking study revealed strong and specific binding interactions with the active site of the Mycobacterial InhA enzyme, in good correlation with experimental data. These results highlight the therapeutic potential of this isoniazid based 1,2,3-triazole derivatives as promising dual-function therapeutic candidates combining direct antitubercular effects with oxidative stress modulation.

Graphical abstract

Keywords: 1,2,3-Triazole; Click reaction; Isoniazid; Antitubercular activity; Antioxidant activity; Molecular docking

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-025-04619-y

Chemical Papers 80 (5) 5207–5222 (2026)