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Synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A

A technology of methyl stearic acid and a synthesis method, applied in the field of drug synthesis, can solve the problems of difficult compound extraction and utilization, difficulty in large-scale planting, and inability to realize industrial application and the like

Active Publication Date: 2014-05-07
山东龙辰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, due to certain defects of natural active compounds, such as too low content, it is difficult to obtain materials from natural raw materials, natural raw materials exist in the wild, or it is difficult to grow them on a large scale, which makes it difficult to extract and utilize the compounds on a large scale, and cannot realize industrial application.
At the same time, natural active compounds also have certain defects, such as unsatisfactory drug effects or some toxic and side effects, which require structural modification. Methyl stringy acid A is a modification of the pharmacodynamic structure of the columbarium compound stringy acid. Improvement, there is no report on the synthesis of the columbarium compound methyl garbusic acid A

Method used

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  • Synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A
  • Synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A
  • Synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A

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Embodiment

[0048] This embodiment provides a method for synthesizing methyl garbusic acid A, a columbarium compound, for synthesizing methyl jacaronic acid A, including the following processes and steps:

[0049]

[0050] 1) Preparation of compound II:

[0051] The compound of formula I (50g) was dissolved in absolute ethanol (250mL), concentrated sulfuric acid (75mL) was added dropwise to the mixed solution, and the reaction solution was refluxed for 24 hours. After the reaction was over, the solvent was evaporated under reduced pressure, extracted 3 times with ethyl acetate, the organic phases were combined, and the organic phase was washed with 10% sodium bicarbonate solution and water for several times, then dried with anhydrous magnesium sulfate, concentrated to obtain 55.3g Colorless liquid compound with a yield of 96%. After nuclear magnetic detection, the compound was confirmed to be a compound of formula (II) after analysis. The nuclear magnetic data is as follows: 1H NMR (4...

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Abstract

The invention discloses a synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A. The synthesis method comprises the steps: esterifying a compound with a formula (I) to generate a compound with a formula (II); reducing the compound with the formula (II) to generate a compound with a formula (III); carrying out substitution on the compound with the formula (III) to generate a compound with a formula (IV); carrying out substitution on the compound with the formula (IV) to generate a compound with a formula (V); carrying out alkylation on the compound with the formula (V) to generate a compound with a formula (VI); carrying out esterolysis on the compound with the formula (VI) to generate a compound with a formula (VII); carrying out decarboxylation on the compound with the formula (VII) to generate a compound with a formula (VIII); carrying out dehydration cyclization on the compound with the formula (VIII) to generate a compound with a formula (IX); carrying out condensation on the compound with the formula (IX) to generate a compound with a formula (X); carrying out five-membered ring breakage on the compound with the formula (X) to generate a compound with a formula (XI); carrying out condensation on the compound with the formula (XI) to generate a compound with a formula (XII); carrying out coupling on the compound with the formula (XII) to generate a compound with a formula (XIII); carrying out esterolysis on the compound with the formula (XIII) to generate a compound with a formula (XIV), namely methyl pigeon pea ketonic acid A.

Description

technical field [0001] The invention relates to a method for synthesizing a columbarium compound methyl galvanic acid A, which has the functions of lowering blood sugar, lowering fat and reducing weight, and belongs to the technical field of drug synthesis. Background technique [0002] The structural formula of the barley-like compound jacaronic acid and methyl jacaronic acid A is as follows: [0003] [0004] It has been known to human beings that the columbarium compound stickyronic acid has the effects of lowering blood sugar, lowering fat and reducing weight. However, the current way to obtain this compound is to extract it from natural medicines. Compounds obtained from natural medicines are only the early stage of a class of innovative drug research. Even though some natural active compounds can be developed into medicines, there is a long way to go from successful isolation, structure determination to real development. Moreover, due to some defects of natural ac...

Claims

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Application Information

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IPC IPC(8): C07C59/90C07C51/09
CPCC07C41/22C07C41/26C07C45/54C07C51/09C07C51/31C07C51/38C07C67/343C07C2602/08C07D311/76C07C59/90C07C59/64C07C69/738C07C49/755C07C69/734C07C43/225C07C43/23
Inventor 王亚农戈平胡英杰卢媛媛
Owner 山东龙辰药业有限公司
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