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Preparation method of Helanadizine

A technology of Hylandizine and Tetrandrine, which is applied in the field of Hylandizine preparation, can solve the problems of unreported Hylandizine recovery rate, difficulty in realizing industrialized production, and increased cost.

Active Publication Date: 2022-03-04
YU JIE BIOTECH SHANGHAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method does not report the recovery rate of hylandrazine, the extraction process produces a large amount of waste acid, the purification process is too complicated, the separation by preparative liquid chromatography will greatly increase the cost, and it is difficult to realize industrial production

Method used

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  • Preparation method of Helanadizine
  • Preparation method of Helanadizine
  • Preparation method of Helanadizine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Preparation of 5-bromotetrandrine

[0031] Tetrandrine is used as raw material, and tetrandrine is used as raw material, and brominated reagent is used in solvent 1 to react to obtain 5-bromotetrandrine. Among them, solvent 1 is an acidic solvent, which is liquid under normal temperature and pressure. These solvents can be used alone or mixed in any proportion; brominated reagents are N-bromosuccinimide, 1,3-dibromo- 5,5-Dimethylhydantoin, bromine simple substance.

[0032] Reactions 1 to 3 in Table 1 are the reaction yields obtained using different brominated reagents; Reaction 4 and Reaction 5 are the yields of ten grams and more of the amplified reaction using N-bromosuccinimide as the brominated reagent :

[0033] Table 1. Bromination reactions of different brominated reagents

[0034] Reaction ID Tetrandrine dosage (grams) brominated reagent Yield (%) 1 0.5 N-Bromosuccinimide 82 2 0.5 1,3-Dibromo-5,5-dimethylhydantoin...

Embodiment 2

[0037] Embodiment 2: the preparation of Helanadizine

[0038] Using 5-bromotetrandrine as raw material to prepare Helanidizine, the reaction process is as follows figure 1 shown.

[0039] 5-Bromotetrandrine in N,N-dimethylformamide and methanol, under the action of a catalyst, undergoes a substitution reaction with sodium methoxide or potassium methoxide to obtain helanadizine; the catalyst is monovalent copper salt or its composite substances, such as cuprous chloride, cuprous bromide, cuprous iodide, Cu 2 Cl 2 -DMF complex, Cu 2 Cl 2 -CO 2 compound etc.

[0040] Reactions 1 to 3 in Table 2 are the reaction yields obtained by using different catalysts to prepare hylanidizine with 5-bromotetrandrine; reactions 4 and 5 are gram-scale amplification reaction yields:

[0041] Table 2. Methoxylation reactions of different catalysts

[0042] Reaction ID Dosage of 5-bromotetrandrine (g) catalyst Yield (%) 1 0.5 Cuprous Bromide 85 2 0.5 Cuprous i...

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Abstract

The invention relates to a preparation method of Helanadizine. The invention discloses a method for preparing helanadizine from 5-bromotetrandrine. The invention also discloses a method for preparing helanadizine by using tetrandrine as a raw material through bromination and methoxylation. The preparation method disclosed in the invention uses tetrandrine as a raw material, has high reaction yield, easy purification of intermediates and products, and can be used for the industrial preparation of helandizine.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and more specifically, the invention relates to a preparation method of helanadizine. Background technique [0002] Hernandezine (Hernandezine), also known as Jinsilian base A, Crane's tangconine. Molecular formula is C 39 h 44 N 2 o 7 , with a molecular weight of 652.79, is a bisbenzylisoquinoline alkaloid. Mainly found in the Ranunculaceae Tang Song grass plants. Pharmacological studies have shown that Helandizine has a variety of biological activities. The total alkaloids and its main component, heritandezine, extracted from the golden silk horsetail by Xu Chengxiong and others have a certain therapeutic effect on P388 leukemia mice, ascites S180 and C26 colon cancer mice. In vitro, Hylandrazine significantly inhibited the growth of mouse leukemia L1210 compact and human oral cancer KB cells, and had a weaker inhibitory effect on mouse normal hematopoietic cells (CFU-GM). (...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/18
CPCC07D491/18
Inventor 秦立玙姚连琦聂丽
Owner YU JIE BIOTECH SHANGHAI CO LTD
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