Citation: 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 shu

Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives

Sun Nan ^a ,
Wang Xing ^b ,
Ding Zhibing ^a ,
Zhang Qi ^a ,
Xu Xu ^a,c,d ,
Xu Haijun ^a,c ,
Wang Shifa ^a,c,d,*,,

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

Corresponding author: Wang Shifa, wsfyyq@njfu.com.cn
Received Date: 20 April 2016
Revised Date: 16 May 2016

Fund Project: National Natural Science Foundation of China 31470529Open Funding of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products JSBEM2014010Natural Science Foundation of the Jiangsu Highter Education Institutions 14KJ220001

Figures(1)

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.
- nopinone,
- pinanyl thiazole derivatives,
- bacteriostatic activity,
- anti-inflammatory activity,
- insecticidal activity
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