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A kind of preparation method of trihydroxyisoflavone

A technology of trihydroxyisoflavone and dimethoxyisoflavone, which is applied in the field of preparation of trihydroxyisoflavone, can solve the problems of no economical and efficient method, few activity research reports, expensive raw materials, etc., and achieves easy access , Simplify industrial operation, low cost effect

Active Publication Date: 2013-03-13
ARMY MEDICAL UNIV
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 3', 4', 7-trihydroxy isoflavone (T1) and 4', 6, 7-trihydroxy isoflavone (T2) are both trihydroxy isoflavones. Due to their novel structures, there are relatively few reports on their activity. few
Although this method has a short route and simple operation, the yield is very low (T1: 30%; T2: 8%), and the raw materials are also expensive and difficult to obtain
[0007] In summary, the preparation of 3', 4', 7-trihydroxy isoflavones (T1) and 4', 6, 7-trihydroxy isoflavones (T2), there is no more economical and efficient method

Method used

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  • A kind of preparation method of trihydroxyisoflavone
  • A kind of preparation method of trihydroxyisoflavone
  • A kind of preparation method of trihydroxyisoflavone

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Embodiment 1 prepares 3 ', 4 ', 7-trihydroxy isoflavone (T1)

[0039] 1-1 Preparation of deoxybenzoin I (compound 3)

[0040] Add 2.5 L of isopropyl ether and 400 g of 3,4-dimethoxyphenylacetonitrile into the reaction flask, stir and dissolve with strong mechanical force, then add 278 g of anhydrous zinc chloride at 0-5°C, and continuously feed dry hydrogen chloride gas to The solution in the reaction flask was saturated, 245 g of resorcinol was added, the temperature was maintained at 0-5°C, and the reaction was carried out with airtight stirring for 12 hours. After standing still, add 5L of 5% dilute hydrochloric acid aqueous solution, raise the temperature to 85°C, stop heating after TLC detects that the reaction is complete, cool to room temperature, a large amount of yellow solid precipitates, filter under reduced pressure, wash the filter residue with water until neutral, recrystallize with ethanol , to obtain a pale yellow-white solid powder, dried to constant w...

Embodiment 2

[0045] Example 2 Preparation of 4', 6, 7-trihydroxyisoflavones (T2)

[0046] 2-1 Preparation of deoxybenzoin II (compound 7)

[0047] Add 2L of isopropyl ether and 240g of p-hydroxyphenylacetonitrile into the reaction flask. After stirring and dissolving with strong mechanical force, add 170g of anhydrous zinc chloride at 0-5°C, continuously feed dry hydrogen chloride gas to saturation, and add 3,4- 200g of dimethoxyphenol, keep at 0-5°C, and keep it under closed stirring for 10h, then add 4L of 5% dilute hydrochloric acid aqueous solution, heat up to 85°C, after TLC detects that the reaction is complete, stop heating, cool to room temperature, and a large amount of yellow solid precipitates . Filtrate under reduced pressure, wash the filter residue with water until neutral, and recrystallize from absolute ethanol to obtain 252 g of deoxybenzoin II (compound 7), which is a light yellow-white solid powder with a yield of 53.8%, mp: 177.6-178.9°C. 1 H NMR (400MHz, DMSO) δppm: ...

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Abstract

The invention discloses a preparation method of 3', 4', 7-trihydroxy isoflavone (T1) and 4', 6, 7-trihydroxy isoflavone (T2). The T1 and T2 are used in military medicine Research. The present invention uses cheap and easy-to-get chemical raw materials: resorcinol and 3,4-dimethoxyphenylacetonitrile or 3,4-dimethoxyphenol and p-hydroxybenzonitrile as starting materials, and the improved Hoesch Reaction, carbo-increasing and ring-closing reaction and three-step reactions such as removing dimethyl protection, respectively obtained 3', 4', 7-trihydroxy isoflavone (T1) and 4', 6, 7-trihydroxy isoflavone (T2 ). The method has the characteristics of economy, high efficiency, environmental protection, industrialization and the like.

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals, and relates to a preparation method of trihydroxyisoflavones, in particular to 3', 4', 7-trihydroxyisoflavones (T1) and 4', 6, 7-trihydroxyisoflavones ( T2) preparation method. Background technique [0002] Isoflavones are a class of important non-nutrient components in soybeans, and early studies have shown that they have significant anti-cancer effects (Steemas A, et al. Environ Toxicol Pharmacol, 1999, 7(3), 209-211). Epidemiological surveys show that the incidence of breast cancer, prostate cancer and rectal cancer in western developed countries is 4 to 10 times that of developing countries (such as China and Japan) where soybean is one of the staple foods (Sun Jiali. Tianjin Pharmacy, 2001; 13(2), 10-12). Studies at the molecular level have also confirmed that isoflavones have the effect of inhibiting the growth and reproduction of breast cancer, prostate cancer, liver cancer and gastric ...

Claims

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Application Information

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IPC IPC(8): C07D311/36
Inventor 李蓉罗圣霖马婷刘晶
Owner ARMY MEDICAL UNIV
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