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Dihydrobenzopyrans ketone compound and uses thereof

A technology of benzopyrans and compounds, which is applied in the field of new dihydrobenzopyrones, can solve the problems of unclear function of non-classical estrogen membrane signaling pathway and the like

Active Publication Date: 2010-06-16
BEIJING SHENOGEN BIOMEDICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the role of the non-canonical estrogen membrane signaling pathway is still unclear

Method used

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  • Dihydrobenzopyrans ketone compound and uses thereof
  • Dihydrobenzopyrans ketone compound and uses thereof
  • Dihydrobenzopyrans ketone compound and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: (S)-2,3-dihydro-7-hydroxyl-2-(4-hydroxyphenyl)-6-[2-(1-pyrrolidinyl)ethyl]-4H-1-benzene Preparation of pyran-4-one (compound 1)

[0045]

[0046] Preparation of Compound B

[0047] Compound A (320 mg, 1.0 mmol) was dissolved in 20 ml of methanol at -78°C, and then ozone was passed through for 20 minutes. Remove the cooling bath, then add 0.5 mL dimethyl sulfide to the above mixture, and stir for 10 minutes. After removing the solvent, the product was separated by column chromatography to obtain product B (260 mg, 88%).

[0048] Preparation of compound 1

[0049] A mixture of compound B (250mg, 0.71mmol), pyrrolidine hydrochloride (252mg, 2.34mmol), sodium acetate (107mg, 1.30mmol), sodium cyanoborohydride (80mg, 1.28mmol) and methanol (4mL) at room temperature Stirring was continued for 5 hours. Then 5 ml of water was added to the above mixture and stirred for 30 minutes. Then the above mixture was extracted with ethyl acetate (3X10mL). The extracts...

Embodiment 2

[0050] Example 2: (S)-2,3-dihydro-7-hydroxyl-2-(4-hydroxyphenyl)-6-[2-(dimethylamino)ethyl]-4H-1-benzo Preparation of pyran-4-one (compound 2)

[0051]

[0052] A mixture of compound B (120 mg, 0.34 mmol), dimethylamine hydrochloride (65 mg, 0.80 mmol), sodium acetate (43 mg, 0.52 mmol), sodium cyanoborohydride (32 mg, 0.51 mmol) and methanol (2 mL) Stir at room temperature for 8 hours. Then 5 ml of water was added to the above mixture and stirred for 30 minutes. Then the above mixture was extracted with ethyl acetate (3X10mL). The extracts were combined and dried over anhydrous sodium sulfate. After removing the solvent, the crude product was purified by column chromatography to obtain the product compound 1 (45 mg, 41%). 1 H NMR (acetone-d6, 300MHz): δ7.48(s, 1H), 7.37((d, J=8.1Hz, 1H), 6.89(d, J=8.7Hz, 1H), 6.23(s, 1H) , 5.37 (dd, J 1 =2.7Hz,J 2 =12.6Hz, 1H), 2.96(dd, J 1 =12.8Hz,J 2 =16.7Hz, 1H), 2.84-2.80(m, 1H), 2.74-2.72(m, 1H), 2.62(dd, J 1 =2.9Hz,J 2 =16....

Embodiment 3

[0053] The in vitro biological test of embodiment 3 formula (I) compound

[0054] Test 3-1:

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Abstract

The invention relates to the new synthesized compound i.e. dihydrobenzo pyrone type and the application thereof, and belongs to the field of the chemical drug. The experiment results shows that the compound (I) can kill the breast cancer cell MCF7 expressing ER Alpha 66, FR Alpha 46 and ER Alpha 36. Moreover, the compound (I) can be served as the regulator of the estrogen receptor ER Alpha 36 fortreatment of the illness caused by the unusual expression of the estrogen receptor ER Alpha 36, such as the tumor, the osteoporosis, the asthma, the heart disease and the senile dementia, etc.

Description

technical field [0001] The invention belongs to the field of medicine and relates to a new class of dihydrobenzopyrone compounds used for preventing and treating tumors, osteoporosis and senile dementia. Background technique [0002] Estrogen is a steroid hormone produced by the endocrine system, and it plays an important role in the reproductive system, bone tissue, cardiovascular, immune system and central nervous system [J.Cell Sci., 2003, 116(4 ):585-586]. The estrogen signaling system plays an important role in the regulation of cell growth, differentiation and apoptosis. The occurrence and development of estrogen-dependent tumors, such as breast cancer, ovarian cancer and endometrial cancer, are closely related to estrogen [J.Steroid Biochem.Mol.Biol., 2002, 81(1): 1- 24; J. Mammary Gland Biol. Neoplasia, 1998, 3(1): 49-61; Curr. Drug Targets Immune. Endocr. Metabol. Disord., 2001, 1(1): 1-12; Cancer Res., 1998 , 58(23): 5367-5373, J.Psychiatry Neurosci., 2002, 27(1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/32A61K31/353A61P35/00A61P19/10A61P11/06A61P9/00
Inventor 李靖孟坤
Owner BEIJING SHENOGEN BIOMEDICAL
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