1-甲基-β-咔啉-3-甲酰甘氨酸的合成

Synthesis of N-[(1-methyl-β-carboline-3-yl)-formyl]-glycine

目的:合成1-甲基-β-咔啉-3-甲酰甘氨酸。方法:以L-色氨酸为原料,先后经Pictet-Spengler缩合、甲基化、芳构化、水解、与甘氨基酸酯偶联、水解共6步反应,生成目标化合物。结果:本实验Pictet-Spengler缩合、芳构化和偶联三步反应的收率分别为95%,65%和37%。在10,1和0.1μmol·L^(-1)浓度下,1-甲基-β-咔啉-3-甲酰甘氨酸苄酯对MCF-7肿瘤细胞株的抑制率分别为61.50%,12.40%和7.24%。结论:本合成路线基本满足了目标化合物合成的实用化要求,1-甲基-β-咔啉-3-甲酰氨基酸及酯作为抗肿瘤结构显示了潜在前景。

Objective: To synthesize N-[(1-methyl-β-carboline-3-yl)-formyl]-glycine. Methods: The target compound was obtained from L-tryptophan via 6-step reactions, including the Pictet-Spengler condensation, methylation, aromatization, hydrolyzation, coupling reaction and hydrolyzation. Results: The yields of the Pictet-Spengler condensation, aromatization and coupling reaction were 95%, 65% and 37%, respectively. The inhibition rate of N-[(1-methyl-β-carboline-3-yl)-formyl]-glycine benzyl ester 10, 1, 0.1μmol·L^(-1) on the MCF-7 human tumor cell line was 61.50%, 12.40% and 7.24%, respectively. Conclusion: The target amino acid and its ester prepared by this convenient synthetic process potentiated an anti-tumor activity.