Chinese Journal of Organic Chemistry >
Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives
Received date: 2016-04-20
Revised date: 2016-05-16
Online 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.
Sun Nan , Wang Xing , Ding Zhibing , Zhang Qi , Xu Xu , Xu Haijun , Wang Shifa . Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2016 , 36(10) : 2489 -2495 . DOI: 10.6023/cjoc201604042
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