Synthesis of isoandrographolide glycoside and ester derivatives

Liu Zhijun; Li Lingzhi; Gu Jun; Li Aixiu

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Synthesis of isoandrographolide glycoside and ester derivatives

更新时间：2025-01-15

- Synthesis of isoandrographolide glycoside and ester derivatives
- Journal of Army Medical University Vol. 33, Issue 8, Pages: 809-812(2011)
- 作者机构：
  
  1. 天津医科大学药学院
  2. 中国人民武装警察部队医学院：天津市职业与环境危害生物标志物重点实验室，药物化学教研室
- 作者简介：
- 基金信息：
- DOI：
  CLC： R284.3;R282.71
- Published：2011，
  
  Published Online：30 April 2011，
- 稿件说明：
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LIU ZHIJUN, LI LINGZHI, GU JUN, et al. Synthesis of isoandrographolide glycoside and ester derivatives. [J]. Journal of army medical university, 2011, 33(8): 809-812.
DOI：

LIU ZHIJUN, LI LINGZHI, GU JUN, et al. Synthesis of isoandrographolide glycoside and ester derivatives. [J]. Journal of army medical university, 2011, 33(8): 809-812. DOI：

摘要

目的合成异穿心莲内酯糖苷及酯类衍生物。方法以DCC为缩合剂，DMAP为催化剂，异穿心莲内酯与芳香酸合成异穿心莲内酯衍生物；苄基保护的酚酸与异穿心莲内酯以DCC为缩合剂，DMAP为催化剂成酯，再经氢化合成异穿心莲内酯酚酸衍生物；异穿心莲内酯与溴代乙酰氧糖在碳酸银催化下经K-K反应后在碱性条件下脱去乙酰基形成糖苷。结果合成了4个异穿心莲内酯糖苷类衍生物及16个酯类衍生物。糖苷类衍生物与单酯类衍生物均与19-OH反应，双酯类衍生物与3-OH、19-OH成酯。所有化合物为粉末状固体。结论合成的化合物结构经

H-NMR和MS表征，其中17个为新化合物。

Abstract

Objective To synthesize isoandrographolide glycoside and ester derivatives. Methods Isoandrographolide aromatic acid ester derivatives were synthesized from isoandrographolide and aromatic acids through esterification using N

N’-dicyclohexylcarbodiimide (DCC) as condensing agent and 4-dimethylaminopyridine (DMAP) as catalyst. Isoandrographolide phenolic acid ester derivatives were synthesized from isoandrographolide and benzyl-protected phenolic acids through esterification and hydrogenation in sequence using DCC as condensing agent and DMAP as catalyst. Isoandrographolide glycoside derivatives were synthesized from isoandrographolide and tetra-O-acetyl-β-D-glucopyranosyl bromide through Koenigs-Knorr reaction and then deacetylation in a basic environment using silver carbonat

e as a catalyst. Results Four isoandrographolide glycoside derivatives and sixteen isoandrographolide ester derivatives were synthesized. The glycoside derivatives and the monoester derivatives were obtained through esterification on the 19-OH of isoandrographolide. The diester derivatives were obtained through esterification on the 3- and 19-OH of isoandrographolide. All the derivatives were powdery solids. Conclusion All the derivatives are confirmed by

H-NMR combined with MS

and seventeen of them are new compounds.

关键词

异穿心莲内酯酯化K-K反应合成

Keywords

isoandrographolideesterificationKoenigs-Knorr reactionsynthesis

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