芳氨基代-α-呋喃葡萄糖衍生物的合成及抗肿瘤活性

doi:10.11944/j.issn.1000-0518.2015.09.150019

摘要/Abstract

摘要：

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)。

关键词: 芳氨基代葡萄糖衍生物, 合成, 抗肿瘤活性

Abstract:

Four novel 1,2-O-isopropylidene-5-arylamino-α-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 MTT method. The results indicate that the anti-tumor activitives of compound 1a1 is better than other three kinds of target compounds on three kinds of tumor cells, especially on A431(IC₅₀:(6.54±1.34) μmol/L).

Key words: arylaminogluofuranose derivatives, synthesis, anti-tumor activity

孙宝丽,张娅玲,王丽丽,张喜全,顾红梅,李宝林. 芳氨基代-α-呋喃葡萄糖衍生物的合成及抗肿瘤活性[J]. 应用化学, 2015, 32(9): 987-993.

SUN Baoli,ZHANG Yaling,WANG Lili,ZHANG Xiquan,GU Hongmei,LI Baolin. Synthesis and Anti-tumor Activities of Arylamino-α-glucofuranose Derivatives[J]. Chinese Journal of Applied Chemistry, 2015, 32(9): 987-993.

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