引用本文:
易卫国, 刘志常, 向莉, 刘西洋, 陈静, 向建南. 13-cis-维A酰衍生物合成方法的改进[J]. 应用化学,
2007, 24(5): 521-524.
Citation: YI Wei-Guo, LIU Zhi-Chang, XIANG Li, LIU Xi-Yang, CHEN Jing, XIANG Jian-Nan. Improvement on the Synthesis of 13-cis-Retinoic Acid Derivatives[J]. Chinese Journal of Applied Chemistry, 2007, 24(5): 521-524.
Citation: YI Wei-Guo, LIU Zhi-Chang, XIANG Li, LIU Xi-Yang, CHEN Jing, XIANG Jian-Nan. Improvement on the Synthesis of 13-cis-Retinoic Acid Derivatives[J]. Chinese Journal of Applied Chemistry, 2007, 24(5): 521-524.
13-cis-维A酰衍生物合成方法的改进
摘要:
改进并建立了以4-二甲氨基吡啶(DMAP)-对甲苯磺酸盐为催化剂,二环己基碳酰亚胺(DCC)为缩合剂直接用13-cis-维A酸与醇、酚或胺合成13-cis-维A酰衍生物的方法。合成了8种新目标化合物,收率80%~95%,核磁共振氢谱和碳谱研究表明,13-cis-维A酰部分的构型均保持不变。合成方法彻底抑制了反应中N-异维A酰基脲的副反应,而且反应条件温和,对于极易异构化的13-cis-维A酸的酯化和酰胺化反应十分有利。
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关键词:
- 药物化学
- / 方法改进
- / 异维A酰化
- / cis-维A酸衍生物
- / 二环己基碳酰亚胺
English
Improvement on the Synthesis of 13-cis-Retinoic Acid Derivatives
Abstract:
To improve the synthetic method of 13-cis-retinoic acid derivatives,the title compounds were synthesized directly from 13-cis-retinoic acid and alcohols,phenols or amines with DCC as the condensation reagent under the catalysis of 4-(dimethylamino) pyridinium p-toluenesulfonate prepared in our lab.Eight new compounds were obtained in 80%~95% yields and in a high isomeric purity,which were characterized by NMR.The side reaction that converts 13-cis-retinoic acid to unreactive N-retinoylurea was completely suppressed.The reaction proceeds under mild conditions and is favorable to the esterification and amidation of thermally-,chemically- and ultraviolet-sensitive 13-cis-retinoic acid and its analogues.
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Key words:
- pharmaceutical chemistry
- / improvement
- / retinoylation
- / 13-cis-retinoic acid derivatives
- / DCC
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