Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2489-2495.DOI: 10.6023/cjoc201604042 Previous Articles     Next Articles



孙楠a, 王欣b, 丁志彬a, 张齐a, 徐徐a,c,d, 徐海军a,c, 王石发a,c,d   

  1. a 南京林业大学化学工程学院 南京 210037;
    b 南京农业大学植物保护学院 南京 210095;
    c 江苏省生物质绿色燃料与化学品重点实验室 南京 210037;
    d 广西林产化学与工程重点实验室 南宁 530008
  • 收稿日期:2016-04-20 修回日期:2016-05-16 发布日期:2016-06-08
  • 通讯作者: 王石发,
  • 基金资助:


Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives

Sun Nana, Wang Xingb, Ding Zhibinga, Zhang Qia, Xu Xua,c,d, Xu Haijuna,c, Wang Shifaa,c,d   

  1. a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b College of Plant Protection, Nanjing Agricultural University, Nanjing 210095;
    c Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037;
    d Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008
  • Received:2016-04-20 Revised:2016-05-16 Published:2016-06-08
  • Supported by:

    Project supported by the Natural Science Foundation of the Jiangsu Highter Education Institutions (No.14KJ220001), the National Natural Science Foundation of China (No.31470529), and the Open Funding of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products (No.JSBEM2014010).

Novel pinanyl thiazole derivatives were synthesized from nopinone which was a derivative from β-pinene by con-densation and cyclization, and their bioactivities were also examined in this paper. Nopinone obtained from oxidation of β-pinene was condensed with thiosemicarbazide into nopinone thiosemicarbazone, and thiazole derivatives 2a~2l were prepared via cyclization of nopinone thiosemicarbazone with α-haloketones. The structures of compounds 2a~2l were characterized with 1H NMR, 13C NMR, IR and HRMS, and the antibacterial activity, anti-inflammatory activity on human umbilical vein endothelial cells (HUVECs), and insecticidal activity on crape myrtle aphids of compounds 2a~2l were also examined. Test results showed that compound 2b was a more potent bactericide and fungicide than others because of its good activities against bacteria and fungi, compound 2a had strong anti-inflammatory activity towards HUVECs and had the similar effect to that of aspirin, and compounds 2e, 2h, 2i and 2k had a certain insecticidal activities against crape myrtle aphids.

Key words: nopinone, pinanyl thiazole derivatives, bacteriostatic activity, anti-inflammatory activity, insecticidal activity