摘要
以苯醌及3-氨基巴豆酸乙酯为原料,经环合、苄基化得到关键中间体5-苄氧基-2-甲基-1H-吲哚-3-甲酸乙酯。关键中间体经水解及酰胺化得到3个目标化合物。关键中间体经磺酰化及水解可再次得到4个目标化合物,共合成7个目标化合物。其化学结构均经高分辨质谱、核磁共振氢谱及碳谱确证。人肝癌Hep G2细胞上的促糖消耗活性显示,所合成化合物均具有一定的促糖消耗活性。其中,5-苄氧基-2-甲基-1-(4-氯苯甲酰基)-吲哚-3-甲酸的降糖活性与先导化合物GY3相当。
Starting from benzoquinone and( E)-ethyl 3-aminobut-2-enoate,the key intermediate ethyl 5-( benzyloxy)-2-methyl-1 H-indole-3-carboxylate was synthesized via cyclization and benzylation,which was subjected to hydrolyzation and final amidation with various aryl acids to give three target compounds.The four desired compounds were also obtained from the key intermediate via sulfonylation and hydrolyzation. All the synthesized target compounds were confirmed by high resolution mass spectrometer( HR-MS) and nuclear magnetic resonance( NMR) H and C spectrum.The glucose-consumption activity assay in Hep G2 cell lines showed that all the synthetic compounds exhibited certain hypoglycemic activity,and 5-benzyloxy-2-methyl-1-( 4-chlorobenzoyl)-indole-3-formic acid demonstrated comparable activity with the lead GY3.
引文
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