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

作　　者：孙楠[1] 王欣[2] 丁志彬[1] 张齐[1] 徐徐[1,3,4] 徐海军[1,3] 王石发[1,3,4] 

机构地区：[1]南京林业大学化学工程学院,南京210037 [2]南京农业大学植物保护学院,南京210095 [3]江苏省生物质绿色燃料与化学品重点实验室,南京210037 [4]广西林产化学与工程重点实验室,南宁530008

出　　处：《有机化学》2016年第10期2489-2495,共7页Chinese Journal of Organic Chemistry

基　　金：江苏省高校自然科学研究(No.14KJ220001);国家自然科学基金(No.31470529);广西林产化学与工程重点实验室开放基金(No.JSBEM2014010)资助项目~~

摘　　要：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.

关 键 词：诺蒎酮 蒎烷基噻唑衍生物 抑菌活性 抗炎活性 杀虫活性 

分 类 号：TQ252.5[化学工程—有机化工]