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Synthetic method of polyhydroxy substituted coumestrol natural product

A technology of coumestrol and natural products, which is applied in the field of synthesis of polyhydroxyl substituted coumestrol natural products, can solve the problems of low yield and long reaction steps, and achieve simple route, simple operation and atom economy high effect

Active Publication Date: 2017-04-19
GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method mostly uses precious metal palladium as a catalyst, the reaction steps are long, and the yield is low
In addition, the synthesis of 1,3,9-trihydroxy-6H-benzofuro[3,2-c]chroman-6-one (Aureol) has not been reported yet

Method used

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  • Synthetic method of polyhydroxy substituted coumestrol natural product
  • Synthetic method of polyhydroxy substituted coumestrol natural product
  • Synthetic method of polyhydroxy substituted coumestrol natural product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Preparation of 3-(2-bromo-4-hydroxyphenyl)-7-hydroxycoumarin (structural formula 3a)

[0033] In a 50mL round bottom flask, add 2-bromo-4-hydroxyphenylacetic acid (25mmol, 5.78g), 2,4-dihydroxybenzaldehyde (25mmol, 3.45g), triethylamine (50mmol, 5.06g), ethyl Anhydride (10 mL), stirred, heated to 110° C. in an oil bath, and reacted for 7 hours. After the reaction was completed, the reaction solution was poured into 50 mL of ice water while it was hot, stirred, and solids precipitated out, filtered with suction, washed the filter cake with water, collected the filter cake, and obtained a light brown solid after drying, which was 3-(2-bromo-4-hydroxyl Phenyl)-7-hydroxycoumarin, weight 7.83g, yield 94%. 1 H NMR (DMSO-d 6,400MHz,ppm)δ10.38(s,OH),9.94(s,OH),7.89(s,1H),7.57(d,J=8.8Hz,1H),7.26(d,J=8.4Hz,1H ),7.11(d,J=2.0Hz,1H),6.86(dd,J=2.0,8.8Hz,1H),6.83(dd,J=2.0,8.4Hz,1H),6.78(d,J=2.0Hz ,1H); 13 C NMR (DMSO-d 6 ,100MHz,ppm)δ161.3,159.6,158.2,155.2,143.0,132.5,129.9...

Embodiment 2

[0037] (1) Preparation of 3-(2-bromo-4-hydroxyphenyl)-7-hydroxycoumarin (structural formula 3a)

[0038] In a 50mL round bottom flask, add 2-bromo-4-hydroxyphenylacetic acid (25mmol, 5.78g), 2,4-dihydroxybenzaldehyde (25mmol, 3.45g), triethylamine (25mmol, 2.53g), ethyl Acid anhydride (10 mL), stirred, heated to 110° C. in an oil bath, and reacted for 7 hours. After the reaction is completed, the reaction solution is poured into 50 mL of ice water while it is hot, stirred, and solids are precipitated, filtered with suction, washed with water, collected, and dried to obtain a light brown solid, which is 3-(2-bromo-4-hydroxyl Phenyl)-7-hydroxycoumarin, weight 6.91g, yield 83%.

[0039] (2) Preparation of 3,9-dihydroxy-6H-benzofuro[3,2-c]chroman-6-one (structural formula 4a)

[0040] In a 50mL microwave reaction flask, add 3-(2-bromo-4-hydroxyphenyl)-7-hydroxycoumarin (5mmol, 1.67g), basic copper carbonate (1mmol, 0.24g), 1,10 -O-phenanthroline (1mmol, 0.19g), potassium hydrox...

Embodiment 3

[0042] (1) Preparation of 3-(2-bromo-4-hydroxyphenyl)-7-hydroxycoumarin (structural formula 3a)

[0043] In a 50mL round bottom flask, add 2-bromo-4-hydroxyphenylacetic acid (25mmol, 5.78g), 2,4-dihydroxybenzaldehyde (25mmol, 3.45g), triethylamine (75mmol, 7.59g), ethyl Acid anhydride (10 mL), stirred, heated to 110° C. in an oil bath, and reacted for 7 hours. After the reaction is completed, the reaction solution is poured into 80 mL of ice water while it is hot, stirred, and solids are precipitated, filtered with suction, washed with water, collected, and dried to obtain a light brown solid, which is 3-(2-bromo-4-hydroxyl Phenyl)-7-hydroxycoumarin, weight 7.16g, yield 86%.

[0044] (2) Preparation of 3,9-dihydroxy-6H-benzofuro[3,2-c]chroman-6-one (structural formula 4a)

[0045] In a 50mL microwave reaction flask, add 3-(2-bromo-4-hydroxyphenyl)-7-hydroxycoumarin (5mmol, 1.67g), copper oxide (1mmol, 0.08g), 1,10-o- Phenanthroline (1mmol, 0.19g), potassium hydroxide (50mmo...

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Abstract

The invention discloses a synthetic method of a polyhydroxy substituted coumestrol natural product. 2-bromine-4-hydroxyphenylacetic acid serves as a raw material to make a condensation reaction with a hydroxy substituted salicylaldehyde compound, and a hydroxy substituted 3-(2-bromine-4-hydroxycyclohexyl phenyl)-7-hydroxy coumarin compound is obtained; and then a hydroxylation / oxidative coupling reaction is made under the condition of a catalyst and microwave heating, and the polyhydroxy substituted coumestrol natural product is obtained. The synthetic method is simple in route, easy and convenient to operate, high in yield, soft in reaction condition, free of needs of precious metal catalyzing, high in atom economy and low in cost, and multiple steps of cascade reactions are made simultaneously.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing natural products of coumestrol substituted with polyhydroxy groups. Background technique [0002] 3,9-Dihydroxy-6H-benzofuro[3,2-c]chroman-6-one (Coumestrol) is a polyhydroxy substituted coumestrol plant found in alfalfa, clover and soybean Estrogen, with various biological activities, such as inhibition of active sphingosine kinase (SPHK1), inhibition of α-glucosidase (α-glucosidase), activation of sirtuin 1 antibody (SIRT 1), human pregnane X receptor antagonist Biological activities such as neuroprotection, and can be used as fluorescent probes for efficient screening of estrogen receptors, etc. (Steroids 2014, 80, 37; Neurol. Biomol.Screen.2014,19,253; J.Agric.Food Chem.2014,62,4298; Food Chem.2011,126,1057; Bioorg.&Med.Chem.Lett.2014,24,2560; Appl.Environ.Microbiol. 2012, 78, 2896). 1,3,9-Trihydroxy-6H-benzofuro[3,2-c]chroman-6-one (Aureol) is a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 邹永盛剑飞徐田龙刘洁位文涛
Owner GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK
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