Synthetic method of houttuynin heterozygous flavonoid compound

A technology of hybrid flavonoids and houttuyniatin, which is applied in the field of synthesis of houttuyniatin hybrid flavonoids, can solve the problems of high cost, cumbersome extraction and separation, etc., and achieve the effect of high yield and simple synthesis method

Active Publication Date: 2018-05-18
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Further research on the anti-herpes virus pharmacological activity of such compounds r...

Method used

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  • Synthetic method of houttuynin heterozygous flavonoid compound
  • Synthetic method of houttuynin heterozygous flavonoid compound
  • Synthetic method of houttuynin heterozygous flavonoid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1: Total synthesis of Houttuynoid G, a hybrid flavonoid of houttuynoid

[0105] route such as figure 2 As shown, the specific steps are as follows:

[0106] ①Preparation of compound II

[0107] References for the preparation method of compound I (Shen, S.D.; Zhang, G.P.; Lei, M.; Hu, L.H. First total synthesis of salvianolic acid C, tournefolic acid A, and tournefolal. ARKIVOC. 2012, 6, 204-213). The obtained 4-benzyl-3-hydroxy-2-iodo-p-hydroxybenzaldehyde was designated as compound I.

[0108] Add 4-benzyl-3-hydroxyl-2-iodo-p-hydroxybenzaldehyde (17g, 48.02mmol), pyridine (Py, 6.8ml), 4-dimethylaminopyridine (DMAP, 293mg, 2.39mmol ), stir. Acetic anhydride (6.8ml) was slowly added dropwise, stirred at room temperature and protected from light for 17h. Remove Py with a rotary evaporator, then adjust the pH to neutral with 10% dilute hydrochloric acid, extract with ethyl acetate (EA), wash the organic phase twice with saturated sodium chloride solution, add...

Embodiment 2

[0137] Example 2: Total Synthesis of Houttuynoid H, a Hybrid Flavone Houttuynoid H

[0138] route such as image 3 As shown, the specific steps are as follows:

[0139] ①Preparation of compound II

[0140] References for the preparation method of compound I (Shen, S.D.; Zhang, G.P.; Lei, M.; Hu, L.H. First total synthesis of salvianolic acid C, tournefolic acid A, and tournefolal. ARKIVOC. 2012, 6, 204-213). The obtained 4-benzyl-3-hydroxy-2-iodo-p-hydroxybenzaldehyde was designated as compound I.

[0141] Add 4-benzyl-3-hydroxyl-2-iodo-p-hydroxybenzaldehyde I (17g, 48.02mmol), pyridine (6.8ml), 4-dimethylaminopyridine (DMAP, 293mg, 2.39mmol) into a 250ml one-port bottle , stir. Acetic anhydride (6.8ml) was slowly added dropwise, stirred at room temperature and protected from light for 17h. Remove Py with a rotary evaporator, then adjust the pH to neutral with 10% dilute hydrochloric acid, extract with ethyl acetate (EA), wash the organic phase twice with saturated sodium...

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PUM

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Abstract

The invention discloses a synthetic method of a houttuynin heterozygous flavonoid compound. The method comprises the steps that a compound 1-I reacts with an acetylation reagent; obtained 1-II and 1-undecyne are subjected to a stirring light-resistant reaction under the protection of inert gas; obtained 1-III and alkali are subjected to a stirring reaction at -10-30 DEG C; obtained 1-IV reacts with 1-acetyl-3,5-bis(benzyloxy)phenol; obtained 1-V and iodine and DMSO are subjected to a stirring reaction at 50-150 DEG C; obtained 1-VI reacts with potassium peroxomonosulfate and p-toluene sulfonicacid on the condition that the pH value is 9-12; obtained 1-VII and acid and water are subjected to a stirring reaction at 80-130 DEG C; obtained 1-VIII and brominated sugar are subjected to a stirring reaction; obtained 1-IX takes off a protecting group, and 1-X is obtained; the 1-X reacts with an oxidant, and i-XI is obtained. The method is simple, and the yield is high.

Description

technical field [0001] The invention belongs to the field of compound synthesis, in particular to a method for synthesizing houttuyfonate hybrid flavonoids. Background technique [0002] The natural products Houttuynoid B, Houttuynoid G, Houttuynoid H, Houttuynoid I, Houttuynoid J, and Houttuynoid L are a kind of flavonoid compound of Houttuynoid, which is a kind of flavonoid compound extracted and isolated from Chinese medicine Houttuynia cordata. The structural formula is as follows: [0003] [0004] Houttuyniatin hybrid flavonoids are a new type of flavonoids with a skeleton structure, which is a natural hybrid of Houttuyniatin and Dendrobimin in Houttuynia cordata. It has been proved by pharmacological experiments that it has good anti-herpes virus (HSV) activity. Preliminary mechanism research shows that it acts on the stage of virus infection, which may be related to major envelope proteins such as gB, gD, gH, and gL, indicating that it has a different mechanism ...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00
CPCC07H1/00C07H17/07Y02P20/55
Inventor 孙平华范吉林简杰高加索汪凡备胡议文符春桃徐振艾郭理宁
Owner JINAN UNIVERSITY
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