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Synthesis process of methoxsalen

A synthesis process, the technology of methoxsalen, applied in the direction of organic chemistry, can solve the problem of low total yield of the process, and achieve the effect of easy purification and short synthesis process route

Active Publication Date: 2011-04-27
WUHAN WUYAO SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both Kong Lingyi's and Wang Laiyou's processes had low total yields

Method used

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  • Synthesis process of methoxsalen
  • Synthesis process of methoxsalen
  • Synthesis process of methoxsalen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Preparation of 2,3,4-trihydroxy-2-chloroacetophenone (3)

[0030] Mix pyrogallol 100g (0.793 mole), chloroacetic acid 78.7g (0.833 mole) and phosphorus oxychloride 60.8g (0.397 mole), react at 60-65°C for 2.5-3 hours, then add water for 1 hour. Cool down to room temperature, stand for crystallization, filter, and dry to obtain 86.3 grams (0.426 moles) of 2,3,4-trihydroxy-2-chloroacetophenone (3) as a brown powder, yield 54%, melting point 168-171°C.

Embodiment 2

[0031] Example 2 Preparation of 2,3,4-trihydroxy-2-chloroacetophenone (3)

[0032] Mix 100 grams (0.793 moles) of pyrogallol, 112 grams (1.19 moles) of chloroacetic acid and 80 grams (0.522 moles) of phosphorus oxychloride, and react at 55-62°C for 1.5-2 hours. The post-treatment method was the same as in Example 1 to obtain 122.5 g (0.549 mol) of product (3), with a yield of 69%.

Embodiment 3

[0033] Example 3 Preparation of 2,3,4-trihydroxy-2-chloroacetophenone (3)

[0034] Mix 100 grams (0.793 moles) of pyrogallol, 100 grams (1.064 moles) of chloroacetic acid and 97.4 grams (0.635 moles) of phosphorus oxychloride, and react at 50-60°C for 2-2.5 hours. The post-treatment method was the same as in Example 1 to obtain 104.3 g (0.515 mol) of product (3), with a yield of 65%.

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Abstract

The invention relates to a synthesis process of methoxsalen. In the process, pyrogallol is used as an initial raw material, and the methoxsalen is prepared by carrying out six-step reaction on the pyrogallol, wherein the total yield is 29%. The synthesis process has the advantages of short synthesis path, simple method, readily-available raw materials and suitability for industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a synthesis process of methoxsalen. Background technique [0002] Methoxsalen (Methoxsalen, 1), also known as xanthotoxin (xanthotoxin), 8-methoxypsoralen (8-MOP), chemical name: 8-methoxy-furanocoumarin, first from Ami (Ammimajus L.) is isolated from the fruit, and is now found mainly in plants such as Umbelliferae and Rutaceae. Methoxsalen is a photosensitizer with strong photosensitivity, and it is mainly used clinically for photochemotherapy to treat chronic skin diseases such as vitiligo and psoriasis (psoriasis). In recent years, it has been found that methoxsalen has a good inactivation effect on various DNA viruses and RNA viruses in the blood, and can also induce tumor cell apoptosis. [0003] The content of xanthotoxin in natural plant resources is 0.1% to 0.3%, which is far from meeting the clinical demand for the drug. Research on its synthesis work abroad...

Claims

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Application Information

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IPC IPC(8): C07D493/04
Inventor 黄璐郭亚兵杨尚金
Owner WUHAN WUYAO SCI & TECH
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