Compound used as estrogen-related receptor regulator and application of compound

A compound, triazole technology, applied in the field of medicinal chemistry, can solve problems such as no treatment means

Active Publication Date: 2014-10-29
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is currently no effective trea

Method used

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  • Compound used as estrogen-related receptor regulator and application of compound
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  • Compound used as estrogen-related receptor regulator and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0229] (4-Hydroxyphenyl)(1-(4-isopropylphenyl)-1-hydrogen-1,2,3-triazol-4-yl)methanone (E050)

[0230] (4-hydroxyphenyl)(1-(4-isopropylphenyl)-1H-1,2,3-triazol-4-yl)methanone

[0231]

[0232] Step a. 4-(tetrahydro-2-hydro-pyran-2-oxyl)benzaldehyde (2)

[0233] 4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde

[0234] At room temperature, 4-hydroxybenzaldehyde (1) (5g, 40.9mmol) was dissolved in anhydrous dichloromethane, protected by argon, and then 3,4-dihydro-2H-pyran (5.6mL, 61.4mmol ) and pyridinium p-toluenesulfonate (0.5g, 2mmol). Stir overnight at room temperature, and the reaction solution is successively washed with saturated NaHCO 3 solution and saturated brine three times, anhydrous Na 2 SO 4 Dried, then filtered and spin-dried, and separated by column chromatography to obtain 8.3 g (98%) of the product.

[0235] 1 HNMR(400MHz, CDCl3)δ9.89(s,1H),7.85-7.81(m,2H),7.17-7.15(m,2H),5.55-5.53(m,1H),3.88-3.82(m,1H) ,3.66-3.61(m,1H),2.05-1.96(m,1H),1.91-1.87(m,2H),1....

Embodiment 2

[0258] (3-Hydroxyphenyl)(1-(4-isopropylphenyl)-1-hydrogen-1,2,3-triazol-4-yl)methanone (E094)

[0259] (3-hydroxyphenyl)(1-(4-isopropylphenyl)-1H-1,2,3-triazol-4-yl)methanone

[0260]

[0261] The synthesis method is as in Example 1.

[0262] 1 HNMR (400MHz, DMSO-d 6 )δ9.86(s,1H),9.50(s,1H),7.93(d,J=8.4Hz,2H),7.74(d,J=7.6Hz,1H),7.68-7.67(m,1H), 7.51(d,J=8.4Hz,2H),7.41(t,J=8.0Hz,1H),7.12-7.09(m,1H),3.06-2.95(m,1H),1.25(d,J=6.8Hz ,6H).

[0263] 13 CNMR (125MHz, DMSO-d 6 )δ185.34, 157.83, 150.31, 147.60, 138.15, 134.48, 130.10, 128.25, 128.13, 121.37, 121.22, 120.96, 116.75, 33.54, 24.11.

[0264] HRMS(ESI):308.1388[M+H] + .

Embodiment 3

[0266] (2-Hydroxyphenyl)(1-(4-isopropylphenyl)-1-hydrogen-1,2,3-triazol-4-yl)methanone (E110)

[0267] (2-hydroxyphenyl)(1-(4-isopropylphenyl)-1H-1,2,3-triazol-4-yl)methanone

[0268]

[0269] The synthesis method is as in Example 1.

[0270] 1 HNMR (400MHz, DMSO-d 6 )δ11.40(s,1H),9.53(s,1H),8.39(dd,J=1.6,8.0Hz,1H),7.93(d,J=8.4Hz,2H),7.59-7.55(m,1H ),7.50(d,J=8.4Hz,2H),7.05-7.02(m,2H),3.06-2.95(m,1H),1.25(d,J=7.2Hz,6H).

[0271] 13 CNMR (125MHz, DMSO-d 6 )δ188.26, 160.29, 149.90, 147.26, 135.47, 133.96, 131.94, 127.85, 127.69, 121.59, 120.75, 119.13, 117.42, 33.08, 23.64.

[0272] HRMS(ESI):308.1393[M+H] + .

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Abstract

The invention discloses a compound used as an estrogen-related receptor regulator and an application of the compound. The compound is a 1-hydrogen-1, 2, 3-triazole compound with a structure as shown in formula (I) as well as pharmaceutical acceptable salt or prodrug molecule. The compound as well as pharmaceutical acceptable salt or prodrug molecule can be used for preparing drugs for adjusting activity of estrogen relevant receptor (ERR), preventing and treating breast cancer (comprising diseases which are free of influence of an anti-estrogen method), prostatic cancer or metabolic diseases. The formula (I) is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and particularly relates to a compound used as an estrogen-related receptor modulator and its application in treating, improving, preventing or inhibiting diseases mediated by ERR activity. Background technique [0002] Whether in the world or in China, chronic diseases represented by malignant tumors, cardiovascular diseases and diabetes are becoming more important long-term threats. On May 19, 2008, the World Health Organization clearly pointed out in its latest report that non-communicable diseases are becoming the deadliest "killer" of human beings. Among them, cancer ranks first. In 2004, 7.4 million people died of cancer worldwide. Among breast cancer types, triple-negative breast cancer (TNBC) and basal-like breast cancer (BLBC) do not express estrogen receptor (ERα), androgen receptor (PR), and human epidermal growth factor receptor-2 (HER -2). There is currently no effective treatm...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D401/06C07D401/04C07D403/04C07F5/02A61K31/4192A61K31/4439A61K31/69A61P35/00A61P3/10A61P3/04A61P3/06A61P3/08A61P9/10A61P9/08A61P1/16A61P5/50
CPCC07D249/06C07D401/04C07D401/06C07D403/04C07F5/025
Inventor 丁克徐石林庄晓曦潘小芬张章段磊陆小云
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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