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Oxygen bridge dicycloheptene compound containing resveratrol group and its preparation method and use method

A technology of resveratrol and bicycloheptene, applied in the field of medicine, can solve the problems of increasing the risk of endometrial cancer and developing drug resistance

Active Publication Date: 2017-09-22
苏州楚凯药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most commonly used therapeutic drugs target ER, but long-term use of estrogen drugs, such as tamoxifen, will produce drug resistance and increase the risk of endometrial cancer and other side effects

Method used

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  • Oxygen bridge dicycloheptene compound containing resveratrol group and its preparation method and use method
  • Oxygen bridge dicycloheptene compound containing resveratrol group and its preparation method and use method
  • Oxygen bridge dicycloheptene compound containing resveratrol group and its preparation method and use method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Example 1: 5-(4-hydroxyphenyl)-6-(4-((E)-3,5-dimethoxystyryl)phenyl)-7-oxo-bridged bicyclo[2.2.1] - Preparation of 5-heptene-2-sulfonic acid-(2-ethylphenyl) ester (14a):

[0107]

[0108] Weigh 3-(4-hydroxyphenyl)-4-(((E)-3,5-dimethoxystyryl)phenyl)furan compound 10 (300mg, 0.753mmol) and ethylene 2-ethyl Phenylsulfonate (192mg, 0.903mmol) was placed in a 25ml two-neck round-bottom flask, and 4ml of anhydrous THF was added to aid in dissolution, then the temperature was slowly raised to 90°C, and the reaction was carried out for 8 hours. TLC detected that the reaction was complete, quenched by adding water, and extracted with ethyl acetate , the organic layer was taken and dried over anhydrous sodium sulfate. Desolvation under reduced pressure, separation and purification by column chromatography, the eluent ratio is petroleum ether:ethyl acetate=5:1, 294.3 mg of brown solid was obtained, the yield was 73%, m.p.110-113°C; 1H NMR (400MHz, Acetone) δ8.80 (s, 1H), 7.5...

Embodiment 2

[0109] Example 2: 5-(4-hydroxyphenyl)-6-(4-((E)-3,5-dimethoxystyryl)phenyl)-7-oxo-bridged bicyclo[2.2.1] - Preparation of 5-heptene-2-sulfonic acid-(3-methoxyphenyl)ester (14b):

[0110]

[0111] Weigh 3-(4-hydroxyphenyl)-4-(((E)-3,5-dimethoxystyryl)phenyl)furan compound 10 (300mg, 0.753mmol) and ethylene 3-methoxy Phenylphenylsulfonate (194mg, 0.903mmol) was placed in a 25ml two-necked round-bottom flask, 4ml of anhydrous THF was added to aid dissolution, and then the temperature was slowly raised to 90°C, and the reaction was carried out for 8h. TLC detected that the reaction was complete, quenched by adding water, and ethyl acetate After extraction, the organic layer was taken and dried over anhydrous sodium sulfate. Desolvation under reduced pressure, separation and purification by column chromatography, the eluent ratio is petroleum ether:ethyl acetate=5:1, 292.8 mg of yellow solid was obtained, the yield was 63%, m.p.98-101°C. 1 H NMR (400MHz, Acetone) δ7.56(t, J=8....

Embodiment 3

[0112] Example 3: 5-(4-hydroxyphenyl)-6-(4-((E)-3,5-dimethoxystyryl)phenyl)-7-oxo-bridged bicyclo[2.2.1] - Preparation of 5-heptene-2-sulfonic acid-(4-bromophenyl) ester (14c):

[0113]

[0114] Weigh 3-(4-hydroxyphenyl)-4-(((E)-3,5-dimethoxystyryl)phenyl)furan compound 10 (300mg, 0.753mmol) and vinyl 4-bromobenzene Sulfonate (274mg, 0.903mmol) was placed in a 25ml two-necked round-bottom flask, 4ml of anhydrous THF was added to aid dissolution, and then the temperature was slowly raised to 90°C, and the reaction was carried out for 8h. TLC detected that the reaction was complete, quenched by adding water, and extracted with ethyl acetate. The organic layer was taken and dried over anhydrous sodium sulfate. Desolvation under reduced pressure, separation and purification by column chromatography, the eluent ratio is petroleum ether: ethyl acetate = 5:1, and 378.6 mg of brown solid was obtained with a yield of 76%, m.p.100-102°C. 1 H NMR (400MHz, Acetone) δ8.74(s, 1H), 7.60...

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Abstract

The invention belongs to the technical field of medicine and discloses a preparation method of an oxygen bridge dicycloheptene compound containing a resveratrol group. One of a 3-(4-hydroxyphenyl)-4-(((E)-3, 5-dihydroxystyryl)phenyl)furan compound and a 3, 4-bis(4-hydroxy-phenyl)furan compound and one of a vinylsulfonate and a vinylsulfonate derivative as raw materials undergo a reaction without a catalyst at 90 DEG C for 8h to produce the oxygen bridge dicycloheptene compound containing a resveratrol group. The oxygen bridge dicycloheptene compound has an action method different from that of the existing anti-breast cancer drug tamoxifen. The oxygen bridge dicycloheptene compound can effectively inhibit growth of breast cancer cells MCF-7 and triple-negative breast cancer cells MDA-MB-231, has good anti-inflammatory activity and has an application prospect in breast cancer treatment.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to an oxo-bridged bicycloheptene compound containing a resveratrol group and a preparation and use method thereof. Background technique [0002] Breast cancer is one of the most common malignant tumors in women and the number one killer of women aged 35-55. In recent years, breast cancer has become a major public health problem in society. The global incidence of breast cancer has been on the rise since the late 1970s. At present, breast cancer has become a common tumor that threatens women's physical and mental health. At present, hormone replacement therapy is mainly used clinically, that is, supplementing estrogen and progesterone to postmenopausal women with estrogen deficiency to relieve their menopausal symptoms. Most of the commonly used therapeutic drugs target ER, but long-term use of estrogen drugs, such as tamoxifen, will produce drug resistance and increase the risk of e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61K31/34A61P35/00
CPCC07D493/08
Inventor 董春娥宁文涛胡志烨刘现军
Owner 苏州楚凯药业有限公司
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