Benzopyrone derivative, preparation method and medical use thereof

A pharmaceutical and compound technology, applied in the field of benzopyrone derivatives to treat ER-type breast cancer, can solve the problems of patients losing fertility

Inactive Publication Date: 2008-08-13
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In these cases, hysterectomy is effective in terminati...

Method used

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  • Benzopyrone derivative, preparation method and medical use thereof
  • Benzopyrone derivative, preparation method and medical use thereof
  • Benzopyrone derivative, preparation method and medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Preparation of m-methoxyphenol (III)

[0059] Dissolve 13.2g of resorcinol equivalent to 0.12mol in 100ml of toluene, add a solution made of 0.5g of tetrabutylammonium bromide, 6.0ml of water and 28.0ml of 5N NaOH, heat up to 50°C, stir and drop Add 13.3ml of dimethyl sulfate equivalent to 0.14mol, and continue to keep warm for 2h. The pH was adjusted to neutral with acetic acid, and the separated aqueous phase was extracted with 30 ml of toluene. The organic phases were combined, washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, distilled under reduced pressure, and the solvent was evaporated to obtain a crude compound III in the form of light yellow liquid, which was directly used in the next reaction.

Embodiment 2

[0061] Preparation of 2-hydroxy-4-methoxy-4'-hydroxydeoxybenzoin (IV)

[0062] Add 9.0 g of p-hydroxyphenylacetic acid corresponding to 0.059 mol, 0.6 g of p-toluenesulfonic acid and 36 ml of freshly steamed boron trifluoride-ether solution to the above system compound III, and react at 80° C. for 6 h. After cooling, slowly pour into 150ml of saturated sodium bicarbonate solution, stir vigorously, filter out the precipitated solid, recrystallize with absolute ethanol, and decolorize with activated carbon to obtain 7.52g of off-white powder with a yield of 48.6%. m.p.150-152°C.

Embodiment 3

[0064] Preparation of 7-methoxydaidzein (V)

[0065] Dissolve 6.0g of compound IV equivalent to 0.023mol, 8.0g of N,N-dimethylacetamide dimethyl acetal (DMF-DMA) equivalent to 0.067mol into 20ml of DMF, heat to reflux for 4h, and cool Then pour it into 100ml of ice water, stir, filter out the precipitated solid, and recrystallize from methanol to obtain 5.11g of light yellow powder with a yield of 82%. m.p.215-218°C. ESI-MSm / z: 267[M-H] - .

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Abstract

The invention relates to medicinal chemistry and organic chemistry fields, particularly to benzopyrone derivatives (I). The compounds are useful in treating various medicinal indication related to post-menopause syndrome, uterus fibre lesion and vascular smooth muscle cell proliferation, especially in treating ER-(+) type breast cancer. The invention also discloses a preparing method of the compounds.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and organic chemistry, in particular to a class of benzopyrone derivatives. These compounds can be used to treat various medical indications related to postmenopausal syndrome, as well as uterine fibropathies and arterial smooth muscle cell hyperplasia, and are especially suitable for treating ER-(+) breast cancer. Background technique [0002] "Postmenopausal syndrome" refers to a variety of pathological conditions caused by the decline of estrogen secretion when women are in or have completed physiological abnormality, that is, menopause. Although the term is used to consider a variety of conditions, the main effects of postmenopausal syndrome are the point of departure for long-term medical concerns, namely osteoporosis, hyperlipidemia, estrogen-dependent breast cancer, and endometrial cancer, among others. [0003] The main pathological conditions associated with postmenopausal syndrome ar...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P15/12A61P19/10A61P35/00
Inventor 向华方维何玲高瑛廖清江尤启冬
Owner CHINA PHARM UNIV
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