异长叶烯基噻唑类化合物的合成及其抑菌、抗肿瘤活性研究

以异长烯酮为原料,通过缩合、亲核取代和环化等手段合成了11种新型异长叶烯基噻唑类化合物,同时采用1H NMR、13C NMR、LC-MS和FT-IR对化合物进行了鉴定,从而确定了化合物的结构。对目标化合物进行了抑菌活性实验,结果表明:(E)-4-(4-甲氧基苯基)-2-(2-(1,1,5,5-四甲基-3,4,5,6-四氢-1H-2,4a-亚甲基-7(2H)-亚基)肼基)噻唑(2e)与(E)-4-(4-甲基苯基)-2-(2-(1,1,5,5-四甲基-3,4,5,6-四氢-1H-2,4a-亚甲基-7(2H)-亚基)肼基)噻唑(2g)对细菌(大肠杆菌与金黄色葡萄球菌)具有较好的抑制效果,最低抑菌质量浓度(MIC)为7.8 mg/L。(E)-4-氯苯基-2-(2-(1,1,5,5-四甲基-3,4,5,6-四氢-1H-2,4a-亚甲基-7(2H)-亚基)肼基)噻唑(2b)对真菌(白念球菌与热带假丝酵母)抑制效果优于其他化合物,其MIC值为15.6 mg/L。采用噻唑蓝(MTT)法对目标化合物进行了人体肝癌细胞(HepG 2)抗癌活性测试,化合物2g(IC50=43.9±0.9 mg/L)对HepG 2具有较好的抗癌活性。

Synthesis of Isolongifolanyl Thiazole Compounds and Their Antibacterial and Antitumor Activities

Eleven new kinds of isolongifolanyl thiazole compounds were synthesized by condensation, nucleophilic substitution and cyclization from isolongifolenone. The structures of the target compounds were characterized by 1H NMR, 13C NMR, LC-MS and FT-IR, respectively. Antibacterial evaluation of the compounds was carried out by minimum inhibitory concentrations assay (MIC). The results showed that the antibacterial activities of (E)-4-(4-methoxyphenyl)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)thiazole(2e) and (E)-2-(2-(1,1,5,5-tetramethyl-3,4,5, 6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)-4-(p-tolyl) thiazole (2g) were better than those of others against Escherichia coli and Staphylococcus aureus. Their MIC were 7. 8 mg/L. The antibacterial activity of ( E )-4-( 4-chlorophenyl)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)thiazole (2b) was better than those of others against fungus. Its MIC value aganist Candida albicans and Candida tropicalis was 15. 6 mg/L. Their antitumor activities against HepG2 were evaluated by thiazole blue test(MTT). Compound 2g (IC50 =43. 9 ± 0. 9 mg/L) was found to be the most potent derivative overall the tested compounds against HepG2.