In silico assessments, Design, synthesis, and biological evaluation of 5-methylisoxazole-4-carboxamide derivatives

Abstract

Isoxazole, a five-membered heterocyclic compound containing oxygen and nitrogen atoms, exhibited potent antioxidant, antibacterial, anticancer, anti-inflammatory, and antiviral activities. The 5-methylisoxazole-4-carboxylic acid molecule serves as a core structure for synthesizing various derivatives through amide bond formation. The main aim of the present work is synthesis of 12 derivatives from 5-methylisoxazole-4-carboxylic acid and evaluating their biological activities, including antimicrobial, antioxidant, and anticancer properties. Results indicate that several synthesised derivatives demonstrated significant biological activity. Notably, molecules 2, 12, and 14 exhibited superior antioxidant activity compared to the standard ascorbic acid, with molecule 14 showing the highest scavenging activity. In antimicrobial study, various compounds elicited potent inhibitory effects against Pseudomonas aeruginosa and Staphylococcus aureus. The anticancer activity revealed that most compounds reduced cell viability in the MCF-7 cell line, with IC50 values generally below 200 μg/mL, except for molecules 2, 11, and 13. This study highlights the potential of 5-methylisoxazole-4-carboxylic acid derivatives as promising candidates for further development in therapeutic applications due to their broad-spectrum biological activities.