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Vol. 35 No. 11 (2023): Vol 35 Issue 11, 2023

Copyright (c) 2023 SUSMITA BASAK, K. ISHWAR BHAT

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Design, Synthesis, Evaluation of Antitubercular and Antioxidant Activity of Isoxazoline Derivatives Derived from Novel Chalcone Intermediates

https://doi.org/10.14233/ajchem.2023.30580
SUSMITA BASAK
Department of Pharmaceutical Chemistry, NGSM Institute of Pharmaceutical Sciences, Nitte (Deemed to be University), Deralkatte-575018, Mangalore, India
https://orcid.org/0000-0003-3122-0308
K. ISHWAR BHAT
Department of Pharmaceutical Chemistry, NGSM Institute of Pharmaceutical Sciences, Nitte (Deemed to be University), Deralkatte-575018, Mangalore, India
https://orcid.org/0000-0002-7545-7780

Corresponding Author(s) : K. ISHWAR BHAT

bhatishwark@nitte.edu.in

Asian Journal of Chemistry, Vol. 35 No. 11 (2023): Vol 35 Issue 11, 2023

Abstract

Tuberculosis (TB), a bacterial infection caused by Mycobacterium tuberculosis (M-TB) is a fatal disease associated with a high degree of mortality. Present work involved synthesis of a series of novel isoxazoline derivatives (ISOA1-ISOA8) the new antitubercular agents using newly synthesized chalcones (CHL1-CHL8). This was done by subjecting the chalcones to a reaction with hydroxylamine hydrochloride in presence of acetic acid and sodium acetate. The structure of the synthesized compounds was elucidated by IR, 1H NMR and mass spectra. In silico studies of isoxazoline were performed for antitubercular activity by using an enoyl acyl carrier protein (EACP) reductase enzyme. Compound ISOA4 exhibited the best interaction among all these compounds having a docking score of -5.94 compared to standard drug pyrazinamide -6.1. Using in vitro models, purified compounds were tested for their antioxidant and antitubercular properties. Compound ISOA5 showed a significant antioxidant activity compared to ascorbic acid as a standard drug. This study claims new isooxazolines to possess high antioxidant and antitubercular potential, however they must be evaluated for preclinical and clinical significance.

Keywords

Isoxazolines Chalcones Antitubercular activity Antioxidant activity Mycobacterium tuberculosis
BASAK, S., & BHAT, K. I. (2023). Design, Synthesis, Evaluation of Antitubercular and Antioxidant Activity of Isoxazoline Derivatives Derived from Novel Chalcone Intermediates. Asian Journal of Chemistry, 35(11), 2782–2788. https://doi.org/10.14233/ajchem.2023.30580
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