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4、5和7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 formamide(1), L-5-hydroxytryptophan acetamide(2), L-5-hydroxytryptophan propionamide(3), L-5-acetoxytryptophan methyl ester(4), L-5-acetoxytryptophan formamide(5), L-5-methoxytryptophan methyl ester(6) and L-5-methoxytryptophan formamide(7), 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

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