大理大学学报 ›› 2023, Vol. 8 ›› Issue (8): 15-20.

• 药学 • 上一篇    下一篇

L-5-羟基色氨酸衍生物的合成

秦子康,郭海慧,单 方,吴 磊,王福生*   

  1. (大理大学药学院,云南大理 671000

  • 收稿日期:2023-01-12 修回日期:2023-02-11 出版日期:2023-08-15 发布日期:2023-07-11
  • 通讯作者: 王福生,教授,博士,E-mail:wfsyn@163.com。
  • 作者简介:秦子康,硕士研究生,主要从事天然药物化学研究。
  • 基金资助:
    国家自然科学基金项目(82260679);云南省地方本科高校基础研究联合专项资金项目(2019FH001-002

Synthesis of L-5-Hydroxytryptophan Derivatives

Qin Zikang Guo Haihui Shan Fang Wu Lei Wang Fusheng*   

  1. College of Pharmacy Dali University Dali Yunnan 671000 China

  • Received:2023-01-12 Revised:2023-02-11 Online:2023-08-15 Published:2023-07-11

摘要: 目的:拓宽色氨酸衍生物的类别,以便合成单萜吲哚生物碱。方法:以商业易得的L-5-羟基色氨酸为原料,经羧基酯化、氨基Boc保护、酯的氨解、羟基的乙酰化或甲基化反应以及脱Boc保护等反应步骤合成L-5-羟基色氨酸衍生物。结果:高效合成了7个L-5-羟基色氨酸衍生物,分别为L-5-羟基色氨酸甲酰胺(1)、L-5-羟基色氨酸乙酰胺(2)、L-5-羟基色氨酸丙酰胺(3)、L-5-乙酰氧基色氨酸甲酯(4)、L-5-乙酰氧基色氨酸甲酰胺(5)、L-5-甲氧基色氨酸甲酯(6)和L-5-甲氧基色氨酸甲酰胺(7)。化合物457为新衍生物,所有衍生物的结构经波谱学方法确证。结论:该合成方法具有操作简单、反应条件温和、总收率高的特点,适用于工业化生产。

关键词: font-family:Times New Roman, ">酯的氨解;乙酰化反应;甲基化反应;font-family:Times New Roman, ">L-5-font-family:Times New Roman, ">羟基色氨酸衍生物;合成

Abstract: Objective To broaden the categories of tryptophan derivatives for the synthesis of monothylindole alkaloids. Methods Using commercially available L-5-hydroxytryptophan as raw material L-5-hydroxytryptophan derivatives were synthesized through carboxyl esterification amino Boc protection ester ammonolysis acetylation or methylation of hydroxyl and deprotection of Boc. Results Secen L-5-hydroxytryptophan derivatives were efficiently synthesized namely L-5-hydroxytryptophan formamide1), L-5-hydroxytryptophan acetamide2), L-5-hydroxytryptophan propionamide3), L-5-acetoxytryptophan methyl ester4), L-5-acetoxytryptophan formamide5), L-5-methoxytryptophan methyl ester6 and L-5-methoxytryptophan formamide7), respectively. Compounds 4 5 and 7 were new derivatives and the structures of all derivatives were confirmed by spectroscopic methods. Conclusion The synthesis method has the characteristics of simple operation mild reaction condition and high total yield which is suitable for industrial production.

Key words: font-family:Times New Roman, ">ester ammonolysisfont-family:Times New Roman, ">;font-family:Times New Roman, "> acetylation reactionfont-family:Times New Roman, ">;font-family:Times New Roman, "> methylation reactionfont-family:Times New Roman, ">;font-family:Times New Roman, "> L-5-hydroxytryptophan derivativefont-family:Times New Roman, ">;font-family:Times New Roman, "> synthesis

中图分类号: