SYNTHESIS AND CHARACTERIZATION OF SOME NEW 5-(4-SUBSTITUTED PHENYL) THIAZOL-2-YL-3-SUBSTITUTED 1, 3, 4-OXADIAZOLE-2-THIONE DERIVATIVES FOR ANTIOXIDANT AND ANTICANCER ACTIVITY
Arman Raja, Anurag Patel, Arpit Singh, Anshika Dubey, Sonam Pal
ABSTRACT
A series of novel 5-(4-substituted phenyl)thiazol-2-yl-3-substituted-1,3,4-oxadiazole-2-thione derivatives were synthesized via a multi-step reaction starting from Claisen–Schmidt condensation of 4-substituted acetophenones with 4-methylthiazol-2-amine, followed by cyclization with thiosemicarbazide. The synthesized compounds were purified by recrystallization and structurally characterized using IR, ?1;H NMR, ?1;?3;C NMR, and mass spectrometry. Yields ranged from 60% to 85%, and purity was confirmed using TLC. Biological evaluation revealed promising antioxidant activity, assessed via the DPPH radical scavenging method, and anticancer activity, evaluated through MTT assays against HeLa and MCF-7 cell lines. Compounds bearing electron-withdrawing groups such as nitro and chloro at the para-position of the phenyl ring exhibited enhanced activity, indicating significant structure–activity relationship (SAR) trends. Physicochemical parameters were found to align with Lipinski’s Rule of Five, supporting their potential as drug-like molecules. These findings underscore the therapeutic relevance of the thiazole–oxadiazole scaffold and suggest these derivatives as promising candidates for further pharmacological development targeting oxidative stress and cancer-related disorders. Future work will involve molecular docking, ADMET profiling, and in vivo validation to support clinical translation.
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