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【目的】将噻唑环构建至异长叶烷酮分子中,得到具有新型生物活性化合物,拓展松节油的应用领域,提高松节油的利用价值。【方法】异长叶烷酮与氨基硫脲缩合,生成异长叶烷酮缩氨基硫脲;异长叶烷酮缩氨基硫脲再与α-溴代苯乙酮衍生物发生环化反应,得到11种异长叶烷基噻唑类化合物2a—2k。采用FT-IR、1H NMR、13C NMR、HPLC-MS等手段,对合成产物的结构进行了表征。采用最低抑制浓度(MIC)法和MTT法分别研究了异长叶烷基噻唑类化合物的抑菌活性和抗肿瘤活性。【结果】化合物4-(4-氯苯基)-2-(2-(1,1,5,5)-四甲基四氢-1H-2,4α-桥亚甲基萘-8(2H,5H,8αH)-亚基)肼基)噻唑(2b)和4-(2-萘基)-2-(2-(1,1,5,5)-四甲基四氢-1H-2,4α-桥亚甲基萘-8(2H,5H,8αH)-亚基)肼基)噻唑(2j)对枯草芽孢杆菌与荧光假单胞菌抑制效果较好,其最低抑制浓度(MIC)为7.5μg/mL,化合物2b对真菌(白色念球菌与热带假丝酵母菌)的抑制效果优于其他化合物,其MIC值均为15.6μg/mL;异长叶烷酮缩氨基硫脲对人体肝癌细胞HepG2的半抑制浓度(IC50)为(34.5±0.8)μg/mL,表明其对HepG2具有较好的抗癌活性。【结论】异长叶烷酮缩氨基硫脲可作为潜在的抗肿瘤药物。
【Objective】 The purpose of this study was to construct the thiazole ring into the iso-long-leaf alkanone and obtain the new bio-active compounds and expand the application field of turpentine, so as to improve the utilization value of turpentine. 【Method】 The condensation of isoprenylalone with thiosemicarbazone led to the production of isoprenone thiosemicarbazone. The cyclodextrin thiosemicarbazone was cyclized with α-bromoacetophenone derivatives, Eleven different-length alkylthiazoles 2a-2k were obtained. The structure of the synthesized product was characterized by FT-IR, 1H NMR, 13C NMR and HPLC-MS. The antibacterial activity and anti-tumor activity of different long-chain alkylthiazoles were studied by the methods of minimum inhibitory concentration (MIC) and MTT. [Results] The compound 4- (4-chlorophenyl) -2- (2- (1,1,5,5) tetramethyltetrahydro-1H-2,4α-methanonaphthalene-8 (5H) -8αH) -ylidene) hydrazino) thiazole (2b) and 4- (2-naphthyl) -2- (2H, 5H, 8αH) -ylidene) hydrazino) thiazole (2j) has a better inhibitory effect on Bacillus subtilis and Pseudomonas fluorescens, and its minimum inhibitory concentration (MIC) Was 7.5μg / mL. The inhibitory effect of compound 2b on fungi (Candida albicans and Candida tropicalis) was better than other compounds, and its MIC value was 15.6μg / mL. The inhibitory effect of isopyrogyn thiosemicarbazone on human The half-inhibitory concentration (IC50) of HepG2 cells was (34.5 ± 0.8) μg / mL, indicating that HepG2 had good anticancer activity. 【Conclusion】 Isoprenaline-thiosemicarbazone can be used as a potential anti-tumor drug.