Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 821-829.DOI: 10.6023/cjoc201807022 Previous Articles     Next Articles



马崇慧a, 吴陈亮a, 王芸芸a, 黄真真b, 张强健a, 董阜豪a, 谷文a,c, 单宇b, 王石发a,c   

  1. a 南京林业大学化学工程学院 南京 210037;
    b 江苏省中国科学院植物研究所 南京 210014;
    c 南京林业大学林业资源高效加工利用协同创新中心 南京 210037
  • 收稿日期:2018-07-11 修回日期:2018-09-24 发布日期:2018-10-20
  • 通讯作者: 单宇, 王石发;
  • 基金资助:


Synthesis and Antitumor Activity of Novel Isolongifolic-Alkyl Dihydropyrimidinethione Derivatives

Ma Chonghuia, Wu Chenlianga, Wang Yunyuna, Huang Zhenzhenb, Zhang Qiangjiana, Dong Fuhaoa, Gu Wena,c, Shan Yb, Wang Shifaa,c   

  1. 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:2018-07-11 Revised:2018-09-24 Published:2018-10-20
  • Contact: 10.6023/cjoc201807022;
  • Supported by:

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

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