新型蒎烷基噻唑衍生物的合成及其生物活性研究
收稿日期: 2016-04-20
修回日期: 2016-05-16
网络出版日期: 2016-06-08
基金资助
江苏省高校自然科学研究（No.14KJ220001）、国家自然科学基金（No.31470529）和广西林产化学与工程重点实验室开放基金（No.JSBEM2014010）资助项目.
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).
以β-蒎烯的衍生物诺蒎酮为原料，合成了系列新型蒎烷基噻唑衍生物，并对其生物活性进行了研究.β-蒎烯经高锰酸钾氧化所得到的诺蒎酮与氨基硫脲进行缩合反应，得到诺蒎酮缩氨基硫脲；诺蒎酮缩氨基硫脲再与α-卤代酮进行环化，得到新型蒎烷基噻唑衍生物2a~2l.采用FTIR，1H NMR，13C NMR和HRMS对化合物2a~2l的结构进行了表征.探讨了化合物2a~2l的抑菌活性、对人脐静脉内皮细胞（HUVECs）的抗炎活性以及对紫薇蚜虫的杀虫活性.结果表明，化合物2b具有很好的抗菌活性，对细菌和真菌的抑制效果分别与阿米卡星和酮康唑的效果相当；化合物2a则具有显著的抗炎活性，化合物2e、2h、2i和2k对紫薇蚜虫具有一定的杀虫活性.
孙楠 , 王欣 , 丁志彬 , 张齐 , 徐徐 , 徐海军 , 王石发 . 新型蒎烷基噻唑衍生物的合成及其生物活性研究[J]. 有机化学, 2016 , 36(10) : 2489 -2495 . DOI: 10.6023/cjoc201604042
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.
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