Synthesis,characterization, and anticancer evaluation of novel 4-hydrazinothiazole analogs |
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Authors: | Shorook Yasser Break Aisha Hossan Asmaa Farouk |
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Affiliation: | 1. Department of Chemistry, Faculty of Science, King Khalid University, Abha, Saudi Arabia;2. National Research Center, Textile Research and Technology Institute, Cairo, Egypt |
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Abstract: | Single-step synthesis of novel 4-hydrazinothiazole derivatives 6a–e was achieved under mild conditions using the sequential four-components method involving isothiocyanate, aminoguanidine, carbonyl adduct, and α-haloketone derivatives. Deprotection of these hydrazinothiazoles was influenced by acylation, providing a novel group of diacylated molecular structures with a broader scope for the design of thiazolyl-containing drugs 7a and 7b . FTIR, 1H/13C NMR, LC–MS spectroscopy, and CHN elemental analyses were used to study the compound chemical structures. Using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on human periodontal ligament fibroblast (HPDLF) cells, the 4-hydrazinothiazole derivatives were screened for cytotoxicity in an in vitro cytotoxicity investigation. The 4-hydrazinothiazole compound 6b bearing an isopropylidene-hydrazino group demonstrated strongly potent cytotoxicity against CAKI1 (IC50 = 1.65 ± 0.24 μM) and A498 (IC50 of 0.85 ± 0.24 μM). Furthermore, the chloroacetyl-containing thiazole compound 7a displayed efficient inhibition of growth against the test cell lines CAKI1 and A498 at low micromolar concentrations, IC50 0.78 and 0.74 μM, respectively. |
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Keywords: | 4-hydrazinothiazoles antirenal cancer activity aromatization cytotoxicity isopropylidene |
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