多肟基柚皮素衍生物的合成与细胞毒活性

Syntheses and Cytotoxicities of Polyoxime Naringin Derivatives

以天然产物柚皮素(1)为原料,分别与α-溴代苯乙酮、α-溴代-4-氯苯乙酮、1-(2-溴乙基)-3-吲哚甲醛、α-溴代丙酮进行醚化反应得到7-(2-氧代-2-苯基乙氧基)柚皮素、7-(2-氧代-2-(4-氯苯基)乙氧基)柚皮素、7-(2-(3-甲酰基吲哚)乙氧基)柚皮素、7,4′-二(2-氧代丙氧基)柚皮素,然后分别与盐酸羟胺、盐酸甲氧胺进行肟化反应,合成了8种多肟基柚皮素衍生物6~13,并通过红外光谱、核磁共振谱及高分辨质谱进行了结构表征。噻唑蓝(MTT)蛋白染色法体外抑制肿瘤增值活性测试显示化合物10、12对人胃癌细胞SGC-7901有较好的抑制活性,其IC_(50)值分别为16.4和15.3μmol/L。

Taking natural product naringenin as raw material,it was etherified withα-bromoacetophenone,4-chloro-α-bromoacetophenone,1-(2-bromoethyl)-indole-3-formaldehyde andα-bromoacetone respectively.Then the intermediate products were subjected to oximation reaction with hydroxylamine hydrochloride and methoxyamine hydrochloride to obtained eight polyoxime naringin derivatives 6~13.Their structures were determined by IR,NMR and HR-MS.The cytotoxic activities of the target compounds were evaluated against SGC-7901 by MTT method in vitro.The results showed that the compounds 10 and 12 display distinct antiproliferative activity against SGC-7901 with the values of IC_(50)16.4 and 15.3μmol/L,respectively.