Synthesis, characterization and anticancer investigation of some novel 2,5-disubstituted-1,3-thiazol-4-(5H)-ones and 1-substituted-1H-pyrazolo[3,4-d] thiazole derivatives

• Published in: Journal of molecular structure Vol. 1322; p. 140352
• Main Authors: Radwan, Eman M., Omran, Mohamed M., Almaaty, Ali H. Abu, El-Hawashey, Mohammed A., Farouk, N.A., Sophy, Mohamed Ahmed Elian
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-02-2025
• Subjects: Anti-Tumor; Apoptosis; HepG2; MCF-7; Thiazolinone; Anti-Tumor; HepG2; Thiazolinone; MCF-7; Apoptosis
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.140352

•2,5-Disubstituted-1,3-thiazole derivatives have been synthesized and characterized by various spectroscopy techniques.•Cytotoxic activity was approved against the MCF7 and HepG2 cell lines.•The anticancer mechanism of compounds (5, 6, and 8a) was shown through apoptosis assessments.•Cell cycle analyses prediction of active compounds, particularly compound (6) shown as a promising lead-like feature.
Fused pyrazoles and 2,5-disubstituted thiazolinone derivatives are attractive molecules for drug design development that are widely recognized as significant biological activity exhibition scaffolds. A considerable number of them were utilized as anti-cancer medications. In this current study, hybrid molecules that exhibited kinase inhibitory activity in addition to anti-tumor properties were synthesized. Our plan was to create a series of disubstituted-1,3-thiazolinone on fused pyrazolo[3,4-d]-thiazole derivatives as efficient anti-cancer drugs with low cytotoxicity and significant biological availability properties using 2-hydroxy acetophenone thiosemicarbazene and ethyl chloroacetate to provide 2-[2-(2-hydroxy phenyl)ethylidene)hydrazinyl]-1,3-thiazole-(5H)-one (3) as the essential precursor to heterocyclization processes. Compounds (3–8) were prepared and identified using infrared, 1H, and 13C NMR spectral data. These synthesized compounds were evaluated for their in vitro cytotoxic activity against the two cancer cell lines (MCF-7 breast cancer and HepG2 liver cancer). The preliminary screening of their compounds for their anti-cancer activity revealed that compound (6) possessed the highest anti-cancer activity. It's interesting to note that these substances, when compared to the reference medicines Erlotinib and Lapatinib, respectively, significantly caused apoptosis in the HepG2 and MCF-7 cell lines using flow cytometry analysis, suggesting potentially high therapeutic ratios.
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