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Synthesis, Characterization, Crystal Structure, and Antitumor Activity of 2-Phenylthiazole–Coumarin Derivatives

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Abstract

2-(4-Methoxyphenyl)-1,3-thiazole4-carboxylic acid was synthesized by condensation, alkylation, and saponification reactions using 4-hydroxythiobenzamide and ethyl 3-bromopyruvate as raw materials. It was then reacted with α,ω-dibromoalkanes to obtain ω-bromoalkyl 2-(4-methoxyphenyl)-1,3-thiazole-4-carboxylates which were condensed with 7-hydroxycoumarins. The structure of the synthesized ω-(2-oxo-2H-chromen-7-yloxy)alkyl 2-(4-methoxyphenyl)-1,3-thiazole-4-carboxylates was confirmed by IR, NMR, and mass spectra and single crystal X-ray diffraction. Their antiproliferation activity against MCF-7 and cisplatin-resistant MCF-7/DDP human breast cancer cell lines was evaluated by using CCK-8 assay. All compounds showed some inhibitory effect at a concentration of 50 µM, and two compounds were found to be potent on both cancer cell lines.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Marine Biotechnology/Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, 222005, Lianyungang, China

    K. Q. Chen, M. Q. Song, W. L. Wu, X. S. Xia, J. H. Hong, S. Yang, J. J. Qian, Q. Yang, J. P. Zou & D. H. Shi

  2. School of Pharmacy, Jiangsu Ocean University, 222005, Lianyungang, China

    K. Q. Chen, M. Q. Song, W. L. Wu, X. S. Xia, J. H. Hong, S. Yang, J. J. Qian, Q. Yang, J. P. Zou & D. H. Shi

  3. Co-Innovation Center of Jiangsu Marine Bioindustry and Technology, 222005, Lianyungang, China

    D. H. Shi

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  1. K. Q. Chen
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Chen, K.Q., Song, M.Q., Wu, W.L. et al. Synthesis, Characterization, Crystal Structure, and Antitumor Activity of 2-Phenylthiazole–Coumarin Derivatives. Russ J Org Chem 58, 1341–1347 (2022). https://doi.org/10.1134/S1070428022090214

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