芳氨基代-α-呋喃葡萄糖衍生物的合成及抗肿瘤活性

Synthesis and Anti-tumor Activities of Arylamino-α-glucofuranose Derivatives

分别以2-甲基-5-硝基苯甲酸、2-氯-5-硝基苯甲酸为原料,经羧基氯化、Friedel-Crafts酰基化、羰基还原、硝基还原和还原胺化反应合成了4种新型的1,2-O-异丙叉基-5-芳氨基代-α-呋喃葡萄糖衍生物。利用IR、NMR和HRMS等技术手段对反应所及中间体及目标化合物进行了结构测定和表征,并采用MTT法将目标化合物对3种人体肿瘤细胞的抗肿瘤活性进行了初步评价。结果表明,目标化合物1a1对肿瘤细胞的生长抑制作用优于其它3种目标化合物,特别是对A431细胞表现出更明显的生长抑制活性(IC50:(6.54±1.34)μmol/L)。

Four novel 1,2-O-isopropylidene-5-arylamino-a-glucofuranose derivatives were prepared using 2-methyl-5-nitrobenzoicacid and 2-chloro-5-nitrobenzoic acid, respectively, as the starting materials by a synthetic route including chlorination of carboxylic acid, Friedel-Crafts acylation, reduction of carbonyl, reduction of nitro and reductive amination. The structures of intermediates and target compounds were characterized by IR, NMR and HRMS. The anti-tumor activities of target compounds on three kinds of cells were tested preliminarily by MTF method. The results indicate that the anti-tumor activitives of compound lal is better than other three kinds of target compounds on three kinds of tumor ceils, especially on A431 （ IC50 ： （6. 54±1.34） μmol/L）.