新型蒎烷基噻唑衍生物的合成及其生物活性研究

Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives

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.

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.