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Synthesis and antitumor activity of novel N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)-2-(piperazin-1-yl)acetamides

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Abstract

A series of novel N-(5-benzyl-4-(tert-butyl) thiazol-2-yl)-2-(piperazin-1-yl)acetamides were designed, synthesized and evaluated for their antitumor activities in vitro. The structures of the synthesized compounds were characterized by 1H NMR, 13C NMR and elemental analysis. In general, compounds 5a, 5c and 6a showed potent antiproliferative activity against HeLa (human cervical cancer) and A549 (human lung cancer) cell lines. Compound 6a, with the best inhibitory activity against HeLa cells (IC50 = 1.6 ± 0.8 μM), was selected to investigate the induced changes of cell morphology in the HeLa cell line by means of acridine orange (AO)/ethidium bromide (EB) double staining and cell cycle analysis using flow cytometry. The results indicated that compound 6a could induce cell apoptosis and cause G1-phase arrest in the cell division cycle.

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Acknowledgments

The authors would like to thank professor Jian-Nan Xiang, College of Chemistry and Chemical Engineering, Hunan University and Professor Kemin Wang (State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan Province, China

    Zhilin Wu, Na Ding, Yuting Tang, Jiao Ye, Junmei Peng & Aixi Hu

  2. School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan Province, China

    Zhilin Wu

  3. Institute of Pharmacy and Pharmacology, University of South China, Hengyang, Hunan Province, China

    Junmei Peng

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  1. Zhilin Wu
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Wu, Z., Ding, N., Tang, Y. et al. Synthesis and antitumor activity of novel N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)-2-(piperazin-1-yl)acetamides. Res Chem Intermed 43, 4833–4850 (2017). https://doi.org/10.1007/s11164-017-2915-6

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