Modification of fish oil triglycerides into 1,2,3-triazole-fatty acid esters as potent antitubercular agents

This study aimed to develop 1,2,3-triazole derivatives from fish oil triglycerides as potential antitubercular agents. The synthetic route consisted of three main steps: hydrolysis of fish oil to obtain free fatty acids (2, yield 86%), propargylation of the free fatty acids to produce propargyl esters (3, yield 59%), and azide-alkyne [3 + 2] cycloaddition of the propargyl esters to afford 1,2,3-triazole esters (5, yield 85%). Linoleic acid was identified as the predominant fatty acid. All compounds were characterized using FTIR, NMR, and HRMS analyses. The final compound (5) demonstrated moderate inhibitory activity against Mycobacterium tuberculosis shikimate kinase (47.86%), whereas the free fatty acids (2) exhibited the strongest inhibition (98.68%) against the enzyme. These findings suggest that linoleic acid and the triazole derivative of the fatty acid represent promising candidates for further development of antitubercular agents.•Commercial fish oil was successfully modified to form 1,2,3-triazole ester derivatives.•The synthetic route involved hydrolysis, propargylation, and azide-alkyne [3 + 2] cycloaddition.•The synthesized compounds showed Mycobacterium tuberculosis shikimate kinase inhibitory activity, thus, it can be considered as potential antitubercular candidates.