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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 3: 821 - 829

DOI: https://doi.org/10.6023/cjoc201807022

Articles

Synthesis and Antitumor Activity of Novel Isolongifolic-Alkyl Dihydropyrimidinethione Derivatives

  • Ma Chonghui ,
  • Wu Chenliang ,
  • Wang Yunyun ,
  • Huang Zhenzhen ,
  • Zhang Qiangjian ,
  • Dong Fuhao ,
  • Gu Wen ,
  • Shan Y ,
  • Wang Shifa
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  • a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b Jiangsu Key Laboratory for the Research and Utilization of Plant Resources, Institute of Botany, Jiangsu Province and Chinese Academy of Sciences, Nanjing 210014;
    c Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037

Received date: 2018-07-11

  Revised date: 2018-09-24

  Online published: 2018-10-20

Supported by

Project supported by the National Natural Science Foundation of China (No. 31470592).

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Abstract

In this work, twelve dihydropyrimidinethione derivatives have been synthesized from isolongifolanone by aldol and cyclization reactions. The chemical structures were characterized by 1H NMR, 13C NMR and high resolution mass spectrometry (HRMS), and the structure of compound 3e was determined by X-ray single crystal diffraction. Their in vitro cytotoxicity against three cancer cell lines breast (MDA-MB-231), cervix (HeLa), liver (HepG-2) and one normal cell line mouse macrophages (Raw-264.7) were investigated. It was shown that these 12 compounds had good antitumor activity with IC50 values of 3.12~44.28 μmol/L. Among them, compounds 3j, 3g, and 3k had the best antitumor activity against MDA-MB-231 cells (IC50=3.12 μmol/L), HeLa cells (IC50=4.04 μmol/L) and HepG-2 cells (IC50=5.43 μmol/L), respectively. In addition, compound 3j arrested the cells in the G0/G1 phase of the MDA-MB-231 cell cycle and induced the early apoptosis of MDA-MB-231 cells in a dose-dependent manner.

Key words： isolongifolanone; dihydropyrimidinethione derivatives; antitumor activity

Cite this article

Ma Chonghui , Wu Chenliang , Wang Yunyun , Huang Zhenzhen , Zhang Qiangjian , Dong Fuhao , Gu Wen , Shan Y , Wang Shifa . Synthesis and Antitumor Activity of Novel Isolongifolic-Alkyl Dihydropyrimidinethione Derivatives[J]. Chinese Journal of Organic Chemistry, 2019 , 39(3) : 821 -829 . DOI: 10.6023/cjoc201807022

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