Synthesis and anticancer evaluation of new 3-allyl-N-(4-fluorophenyl)-4-substituted thiazol-2(3H)-imines on A431 skin cancer cells, revealing cytotoxicity, apoptosis, and cell cycle modulation

Abdel-Wahab, Bakr F., Kishta, Mohamed S., Mohamed, Hanan A., Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897 and El-Hiti, Gamal A. 2025. Synthesis and anticancer evaluation of new 3-allyl-N-(4-fluorophenyl)-4-substituted thiazol-2(3H)-imines on A431 skin cancer cells, revealing cytotoxicity, apoptosis, and cell cycle modulation. Journal of Molecular Structure 1346 , 143195. 10.1016/j.molstruc.2025.143195

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Abstract

Five novel 3-allyl-N-(4-fluorophenyl)-4-substituted thiazol-2(3H)-imines were synthesized in high yields. The synthesis involved a one-pot reaction using an equimolar mixture of 4-flouroaniline, allyl isothiocyanate, and 2-bromomethyl ketone in boiling dry ethanol, in the presence of triethylamine as a base for 4 h. The structures of the synthesized heterocycles were established using spectroscopy data and confirmed by X-ray crystallography. The synthesized heterocycles exhibit strong anticancer potential. The MTT assay indicated dose-dependent cytotoxicity. ELISA results revealed a significant reduction in TNF-α protein levels in A431 cells, suggesting anti-inflammatory activity. The compounds also influenced apoptosis-related proteins, increasing pro-apoptotic Bax and decreasing anti-apoptotic Bcl-2. Flow cytometry revealed that these compounds induced considerable late apoptosis and necrosis.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Elsevier
ISSN:	0022-2860
Date of Acceptance:	1 July 2025
Last Modified:	08 Jul 2025 10:00
URI:	https://orca.cardiff.ac.uk/id/eprint/179578

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