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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 4: 1452 - 1461

DOI: https://doi.org/10.6023/cjoc202210023

ARTICLES

Design, Synthesis and in vitro Anti-Cancer Activity of Novel Ethyl 4-Oxo-2-iminothiazolidin-5-ylidene Acetates

  • Yumei Zhong ,
  • Xiaoying Zou ,
  • Xiaoya Zhuo ,
  • Yihan Wang ,
  • Jiayi Shen ,
  • Lüyin Zheng ,
  • Wei Guo
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  • Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University,Ganzhou, Jiangxi 341000
* Corresponding author. ;

Received date: 2022-10-21

  Revised date: 2022-11-23

  Online published: 2022-12-14

Supported by

National Natural Science Foundation of China(22167002); National Natural Science Foundation of China(21867001); Education Department of Jiangxi Province(GJJ201429); Graduate Innovation Research Project of Gannan Normal University(YCX21A027)

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Abstract

A series of novel ethyl 4-oxo-2-iminothiazolidin-5-ylidene acetate derivatives were synthesized through the three- component coupling annulation of amines, isothiocyanates and diethyl but-2-ynedioates. The obtained compounds were assayed in vitro for their anti-cancer activities against human liver cancer (HepG2) and human breast cancer (MCF-7) cell lines by standard methyl thiazolyl tetrazolium (MTT) method, most of which exhibited significant cytotoxicity. In particular, ethyl (Z)-2-((Z)-2-((3,4-dichlorophenyl)imino)-3-(3-(4-methylpiperazin-1-yl)propyl)-4-oxothiazolidin-5-ylidene)-acetate (4r) displayed the highest level of cytotoxicity compared with cisplatin, and its IC50 values for HepG2 and MCF-7 cells were 0.88 and 0.80 μmol/L, respectively. Their preliminary structure-activity relationship was also discussed. The remarkable cytotoxic nature of these substances against cancer cells could be considered as promising chemotherapeutic agents to be developed in future.

Key words： ethyl 4-oxo-2-iminothiazolidin-5-ylidene acetate; anti-cancer activity; structure-based drug design; structure- activity relationship

Cite this article

Yumei Zhong , Xiaoying Zou , Xiaoya Zhuo , Yihan Wang , Jiayi Shen , Lüyin Zheng , Wei Guo . Design, Synthesis and in vitro Anti-Cancer Activity of Novel Ethyl 4-Oxo-2-iminothiazolidin-5-ylidene Acetates[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1452 -1461 . DOI: 10.6023/cjoc202210023

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