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Oxo-bridged bicyclo-heptylene sulfonamides compound containing different alkyl chain lengths, as well as preparation method and application thereof

A cycloheptene sulfonamide and compound technology, applied in the application field of anti-breast cancer drugs, can solve problems such as drug resistance

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

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Problems solved by technology

[0006] In order to better solve the problems of drug resistance in the clinical treatment of existing breast cancer drugs and enhance the anti-proliferation activity of tumor cells, it is necessary to develop more and better anti-cancer activities, protein degradation activities, and tissue-selective new anti-breast cancer drugs. Drugs, broadening the choice of clinical drugs

Method used

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  • Oxo-bridged bicyclo-heptylene sulfonamides compound containing different alkyl chain lengths, as well as preparation method and application thereof
  • Oxo-bridged bicyclo-heptylene sulfonamides compound containing different alkyl chain lengths, as well as preparation method and application thereof
  • Oxo-bridged bicyclo-heptylene sulfonamides compound containing different alkyl chain lengths, as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] The features and advantages of the present invention can be further understood through the following detailed description in conjunction with the accompanying drawings. The examples provided are only illustrative of the method of the present invention and do not limit the rest of the present disclosure in any way. [Example 1] Synthesis of 3-(4-hydroxyphenyl)-4-alkoxyphenylfuran derivatives

[0097] Synthesis of p-methoxybromoacetophenone compound 2

[0098] Weigh p-methoxyacetophenone 1 (3.499g, 23.3mmol), p-toluenesulfonic acid (0.809g, 4.65mmol) and N-bromosuccinimide (5.02g, 27.9mmol) in a 150mL round bottom In the flask, add 30mL of chloroform, react at room temperature for 12h, TLC monitors that the reaction is complete, add water to quench, extract with dichloromethane (3×15ml), dry the organic layer over anhydrous sodium sulfate, desolvate under reduced pressure, and purify through a silica gel column. 3.2 g (60%) of a yellow solid were obtained.

[0099] Synt...

Embodiment 2

[0110] 5-(4-butoxyphenyl)-6-(4-hydroxyphenyl)-N-(4-methoxyphenyl)-N-(2,2,2-trifluoroethyl)-7 -Oxy-bridge bicyclo[2.2.1]-5-heptene-2-sulfonamide (21a-1),

[0111] 5-(4-hydroxyphenyl)-6-(4-butoxyphenyl)-N-(4-methoxyphenyl)-N-(2,2,2-trifluoroethyl)-7 -Oxy-bridged bicyclo[2.2.1]-5-heptene-2-sulfonamide (21a-2)

[0112]

[0113] Weigh 3-(4-hydroxyphenyl)-4-(4-butoxyphenyl)furan compound 8a (132mg, 0.43mmol) and N-(4-methoxyphenyl)-N-(2, 2,2-Trifluoroethyl)vinylsulfonamide compound 12a (152mg, 0.52mmol) was placed in a 25ml two-necked round-bottomed bottle, and 3ml of anhydrous THF was added to aid dissolution, then the temperature was slowly raised to 90°C, and the reaction was carried out for 8 hours, and the reaction was detected by TLC complete, quenched with water, extracted with ethyl acetate, took the organic layer and dried over anhydrous sodium sulfate. Desolvation under reduced pressure, separation and purification by column chromatography, the eluent ratio is petrol...

Embodiment 3

[0115] 5-(4-pentyloxyphenyl)-6-(4-hydroxyphenyl)-N-(4-methoxyphenyl)-N-(2,2,2-trifluoroethyl)-7 -Oxy-bridged bicyclo[2.2.1]-5-heptene-2-sulfonamide (21b-1),

[0116] 5-(4-Hydroxyphenyl)-6-(4-pentyloxyphenyl)-N-(4-methoxyphenyl)-N-(2,2,2-trifluoroethyl)-7 -Oxy-bridged bicyclo[2.2.1]-5-heptene-2-sulfonamide (21b-2)

[0117]

[0118] Weigh 3-(4-hydroxyphenyl)-4-(4-pentyloxyphenyl)furan compound 8b (145mg, 0.45mmol) and N-(4-methoxyphenyl)-N-(2, 2,2-Trifluoroethyl)vinylsulfonamide compound 12a (159mg, 0.54mmol) was placed in a 25ml two-necked round-bottomed bottle, and 3ml of anhydrous THF was added to aid dissolution, then the temperature was slowly raised to 90°C, and the reaction was carried out for 8 hours, and the reaction was detected by TLC complete, quenched with water, extracted with ethyl acetate, took the organic layer and dried over anhydrous sodium sulfate. Desolvation under reduced pressure, separation and purification by column chromatography, the eluent ratio...

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Abstract

The invention discloses an oxo-bridged bicyclo-heptylene sulfonamides compound containing different alkyl chain lengths, as well as a preparation method and application thereof, and belongs to the technical field of medicines. 3-(4-hydroxycyclohexyl phenyl)-4-(4-alkoxy phenyl)-furan and a phenylethylene sulfonamide derivative are adopted as raw materials, no catalyst is needed, the raw materials are reacted at 90 DEG C for 8 hours, and the oxo-bridged bicyclo-heptylene sulfonamides compound containing the different alkyl chain lengths is obtained through one-step preparation. The action mode of the oxo-bridged bicyclo-heptylene sulfonamides compound is different from the action mode of existing anti-breast cancer drug tamoxifen, and the compound not only can be used for effectively inhibiting the growth of a breast cancer cell MCF-7, but also has favorable estrogen receptor alpha down-regulation activity equivalent to fulvestrant, and shows an application prospect of the compound in breast cancer therapy.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a synthesis method of oxo-bridged bicycloheptene sulfonamide compounds containing different alkyl chain lengths and its application in anti-breast cancer drugs. Background technique [0002] Among many cancers, breast cancer is one of the most common malignant tumors threatening women's health worldwide. Although five-year survival rates for the disease have improved in developed countries, the incidence remains high and patients tend to be younger. At present, hormone replacement therapy is mainly used clinically. Although it has made a major contribution to the treatment of ER-positive breast cancer, long-term use of estrogen drugs, such as tamoxifen, will produce a series of side effects such as drug resistance. , which seriously hinders the development of estrogen replacement therapy. Researchers have speculated that some mechanisms of drug resistance arise, such as ERα rece...

Claims

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Application Information

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IPC IPC(8): C07D493/08A61K31/34A61P35/00
CPCA61P35/00C07D493/08Y02P20/55
Inventor 周海兵吴叔文蓝柯胡志烨宁文涛李媛媛董春娥
Owner WUHAN UNIV
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