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Preparation method and applications of isoflavone type compounds with selective estrogen receptor modulating activity

A compound, isoflavone technology, applied in the field of medicinal chemistry, can solve the problems of few literature reports

Inactive Publication Date: 2011-08-24
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But in general, there are not many reports about the use of isoflavones as selective estrogen receptor modulators

Method used

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  • Preparation method and applications of isoflavone type compounds with selective estrogen receptor modulating activity
  • Preparation method and applications of isoflavone type compounds with selective estrogen receptor modulating activity
  • Preparation method and applications of isoflavone type compounds with selective estrogen receptor modulating activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Daidzein (1a)

[0084] Add 1.1g (10mmol) of resorcinol and 1.52g (10mmol) of p-hydroxyphenylacetic acid to the freshly steamed BF 3 In 6ml of diethyl ether, heat to an internal temperature of 70°C, react for 3h, cool down, add 8ml of dry DMF in an ice bath, heat up to 55°C, add dropwise a mixture of 4ml of methanesulfonyl chloride and 6ml of DMF, dropwise after 0.5h, gradually Raise the temperature to 70°C for 3 hours, cool, pour into 50ml of ice water, filter with suction, wash with water, dry, recrystallize with ethanol to obtain 2.2g of light white solid, yield 86.6%, mp316-319°C.

Embodiment 2

[0086] Genistein (1b)

[0087] 3.8 grams (0.03mol) of phloroglucinol, 4.0 grams (0.03mol) of p-hydroxyphenylacetonitrile, anhydrous ZnCl 2 Put 2.5 g (0.018 mol) and 50 ml of diethyl ether in a reaction bottle, and inject HCl gas at about 0°C under stirring, gradually an orange solid is produced, and seal it overnight. The next day, diethyl ether was poured off, 50ml of water was added to reflux for 3 hours, and suction filtration and drying gave 7.3 grams of powdery yellow solid (2,4,6,4′-tetrahydroxydeoxybenzoin), yield 93.6%, mp 250°C (decomposition) .

[0088] 1.3 g (5 mmol) of 2,4,6,4′-tetrahydroxydeoxybenzoin was dissolved in 20 ml of DMF, and BF was added below 10°C 3 ·Et 2 O 6ml, stirred at room temperature for 30min, heated, and added CH dropwise at about 60oC 3 SO 2 Cl solution (10mlCH 3 SO 2 Dissolve Cl in 20ml DMF), drop it in 30 minutes, heat up to 90-100°C, react for 4 hours to obtain a light brown-black reaction solution, pour the reaction solution into 2...

Embodiment 3

[0090] 7-(3-Bromopropoxy)-4'-hydroxyisoflavone (3a)

[0091] 1.3g (5.1mmol) of daidzein, 30ml of N,N-dimethylformamide, 0.7g (5.1mmol) of potassium carbonate, a small amount of potassium iodide, 1.1g (5.4mmol) of 1,3-dibromopropane, stirred at room temperature for 24h , filtered into 100ml of cold water, neutralized to pH3-4 with 10% HCl, extracted with ethyl acetate (50mL, 30mL×3), washed with water (15mL×2), anhydrous MgSO 4 After drying, the ethyl acetate was distilled off to obtain the crude product, which was separated by column layer (ethyl acetate:petroleum ether=2.5:1) to obtain 350 mg of light yellow solid, yield 18.7%, mp: 175-177°C. 1 H-NMR (300MHz, acetone): δ2.28-2.36 (m, 2H, CH 2 ), 3.82-3.86 (t, 2H, J=6.5Hz, CH 2 Br), 4.31-4.35(t, 2H, J=6.0Hz, CH 2 O), 6.88-6.91 (dd, 2H, J=6.6, 2.0Hz, 3', 5'-H), 7.06-7.10 (dd, 1H, J=8.8, 2.4Hz, 6-H), 7.09-7.10 (d, 2H, J=2.4Hz, 8-H), 7.47-7.50 (dd, 2H, J=6.6, 2.0Hz, 2', 6'-H), 8.09-8.12 (d, 1H, J=8.8 Hz, 5-H), 8.18(s, 1H, 2-...

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Abstract

The invention relates to the pharmaceutical chemistry field, in particular to isoflavone type compounds (I), a preparation method of the compounds, medicinal composites with the compounds and medicinal applications of the compounds and the medicinal composites, in particular to the applications used as a selective estrogen receptor modulator.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a class of isoflavone compounds (I), their preparation methods, pharmaceutical compositions containing these compounds and their medical uses, especially as selective estrogen receptor modulators use. Background technique [0002] Estrogen has a wide range of biological effects. It not only plays an irreplaceable role in the development of female reproductive organs and the maintenance of secondary sexual characteristics, but also plays an important role in bone metabolism, lipid metabolism, cardiovascular system, nervous system, etc. important regulatory role. After women enter menopause, the level of estrogen in the body drops significantly, which can not only lead to a series of autonomic nervous system dysfunction, but also may cause diseases such as coronary heart disease, atherosclerosis and osteoporosis. Although traditional estrogen replacement therapy can tre...

Claims

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Application Information

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IPC IPC(8): C07D311/38A61K31/5377A61K31/496A61K31/4025A61K31/352A61P35/00A61P15/00A61P19/10A61P15/12A61P9/10
Inventor 芦金荣黄文龙江振洲张娟
Owner CHINA PHARM UNIV