Benzoselenazole compound as well as preparation method and application thereof

A technology of benzoselenazoles and compounds is applied in the fields of benzoselenazoles and their preparation, and the application fields of ligands, and can solve the problem that the specific function of ERβ is not very clear.

Inactive Publication Date: 2018-11-23
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

People have extensively studied the physiological role of ERα in tissue distribution and system, but the specific function of ERβ is still not very clear.

Method used

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  • Benzoselenazole compound as well as preparation method and application thereof
  • Benzoselenazole compound as well as preparation method and application thereof
  • Benzoselenazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] [Example 1] Preparation of 4-(benzo[d][1,3]selenazol-2-yl)phenol (compound 1)

[0056]

[0057]Under the condition of anhydrous and oxygen-free, add 0.1mmol o-iodoaniline, 0.12mmol 4-methoxybenzaldehyde, 0.3mmol selenium powder, 0.005mmol copper, 0.2mmol potassium hydroxide and 10ml DMSO solution, in a single port round bottom In the flask, reflux the reaction at 120° C., monitor the reaction by TLC, and separate by column chromatography to obtain pure methoxy-containing benzoselenazole compounds, and then use boron tribromide (3eq.) to demethylate to obtain the reaction product. The product was a white solid in 38% yield.

[0058] 1 H NMR (400MHz, Acetone-d 6 )δ9.14(s,1H),8.07(d,J=7.3Hz,1H),8.00(d,J=8.2Hz,1H),7.95(d,J=8.7Hz,2H),7.47(s, 1H), 7.35–7.28(m, 1H), 7.00(d, J=8.7Hz, 2H). 13 C NMR (100MHz, Acetone-d 6 )δ172.69, 161.37, 157.02, 138.71, 130.54, 128.88, 127.22, 125.99, 125.78, 124.96, 116.88.

Embodiment 2

[0059] [Example 2] Preparation of 4-(benzo[d][1,3]selenazol-2-yl)-2-fluorophenol (compound 2)

[0060]

[0061] Under anhydrous and oxygen-free conditions, add 0.1mmol o-iodoaniline, 0.12mmol 3-fluoro4-methoxybenzaldehyde, 0.3mmol selenium powder, 0.005mmol copper, 0.2mmol potassium hydroxide and 10ml DMSO solution, in a In a single-necked round bottom flask, reflux reaction at 120°C, monitor the reaction by TLC, separate by column chromatography to obtain pure benzoselenoazole compounds containing methoxy groups, and then use boron tribromide (3eq.) to demethylate to obtain the reaction Product, the product is a white solid, the yield is 35%. 1 H NMR (400MHz, Acetone-d 6 )δ9.50(s,1H),8.10(dd,J=7.9,1.2Hz,1H),8.02(dd,J=8.2,1.1Hz,1H),7.86(dd,J=11.8,2.2Hz,1H ),7.73(ddd,J=8.4,2.2,1.0Hz,1H),7.51(ddd,J=8.3,7.2,1.3Hz,1H),7.34(ddd,J=8.3,7.3,1.3Hz,1H), 7.16(t,J=8.6Hz,1H). 13 C NMR (100MHz, Acetone-d 6 )δ171.38, 156.78, 153.65, 151.24, 148.89, 148.76, 138.97, 129.43, 127.36, 126...

Embodiment 3

[0062] [Example 3] Preparation of 4-(5-chlorobenzo[d][1,3]selenazol-2-yl)phenol (compound 3)

[0063]

[0064] Under anhydrous and oxygen-free conditions, add 0.1mmol 2-iodo-3-chloroaniline, 0.12mmol 4-methoxybenzaldehyde, 0.3mmol selenium powder, 0.005mmol copper, 0.2mmol potassium hydroxide and 10ml DMSO solution, in a In a single-necked round bottom flask, reflux reaction at 120°C, monitor the reaction by TLC, separate by column chromatography to obtain pure benzoselenoazole compounds containing methoxy groups, and then use boron tribromide (3eq.) to demethylate to obtain the reaction Product, the product is a white solid, the yield is 34%. 1 H NMR (400MHz, Acetone-d 6 )δ8.10(d, J=8.5Hz, 1H), 7.99(d, J=2.1Hz, 1H), 7.95(d, J=8.7Hz, 2H), 7.34(dd, J=8.5, 2.1Hz, 1H),7.00(d,J=8.7Hz,2H). 13 C NMR (101MHz, Acetone-d 6 )δ175.31, 158.04, 137.09, 132.75, 132.67, 130.71, 128.48, 127.25, 125.72, 124.30, 116.94.

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Abstract

The invention discloses a benzoselenazole compound as well as a preparation method and application thereof and belongs to the technical field of medicines. The preparation method of the benzoselenazole compound is characterized by preparing a series of methoxy-containing benzoselenazole compounds from o-iodoaniline derivatives, benzaldehyde derivatives and selenium under catalysis of copper through a one-pot process, and finally carrying out boron tribromide demethylation to obtain a hydroxy-containing benzoselenazole compound. In-vitro experiments show that the benzoselenazole compound as a ligand of an oestrogen receptor ER beta shows excellent agonist effect; the correlation research shows that the compound as an ERb ligand has treatment effect in animal model of rheumatic arthritis andintestinal diseases caused by inflammation, so that the benzoselenazole compound has potential treatment effect in treatment of rheumatic arthritis and intestinal diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a benzoselenazole compound, a preparation method thereof and an application as a ligand of an estrogen receptor ERβ. Background technique [0002] Estrogen plays a very important role in the maintenance of the development and function of various tissues in the human body, such as the reproductive system, cardiovascular system, nervous system, and bones. Estrogen acts through two estrogen receptors α and β . In human tissues, these two receptors have distinctly different distribution patterns. Even if the two receptor subtypes exist in the same tissue or the same cell, they play different roles in specific gene regulation, resulting in different physiological effects. Estrogen plays an important physiological role in multiple tissues and systems in the body through the regulation of α and β receptors. People have extensively studied the physiological role of ERα in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D293/06A61P35/00
CPCA61P35/00C07D293/06
Inventor 周海兵张思龙胡志烨李媛媛宁文涛董春娥
Owner WUHAN UNIV
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