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17-amide estrogen compound and its preparation method and application

A compound, estrogen technology, applied in the field of 17-amide estrogen compounds

Inactive Publication Date: 2021-12-07
GUANGXI TEACHERS EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the introduction of branched chain amides and aromatic ring amides on estradiol has not been reported in the literature.

Method used

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  • 17-amide estrogen compound and its preparation method and application
  • 17-amide estrogen compound and its preparation method and application
  • 17-amide estrogen compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of N-((17β)-3-hydroxyl-1,3,5(10)-estratrien-17-yl)-o-methoxybenzamide:

[0045] Take 150 mg of the second compound 2, dissolve it in 10 mL of dichloromethane, add 1 mL of triethylamine, slowly add 90 μL of o-methoxybenzoyl chloride, follow the reaction by TLC, react at room temperature for 3 h, spin dry under reduced pressure, and extract with ethyl acetate three times , washed 2 times with water, washed 1 time with saturated brine, dried over anhydrous sodium sulfate, spin-dried, separated by column chromatography (eluent is V 二氯甲烷 :V 甲醇 =100:1), a white solid was obtained with a yield of 20%, m.p.235~236°C, and the structure of the product was determined to be N-((17β)-3-hydroxyl-1,3,5(10 )-estratrien-17-yl)-o-methoxybenzamide, its chemical structure is as shown in the following formula:

[0046]

[0047] Among them, R=R 1 =

Embodiment 2

[0049] Synthesis of N-((17β)-3-hydroxyl-1,3,5(10)-estratrien-17-yl)-p-toluamide:

[0050] Take 2150 mg of the second compound, dissolve it in 10 mL of dichloromethane, add 1 mL of triethylamine, slowly add 66 μL of p-toluoyl chloride, follow the reaction by TLC, react at room temperature for 3 h, spin dry under reduced pressure, extract with ethyl acetate three times, wash with water 2 times, washed 1 time with saturated brine, dried over anhydrous sodium sulfate, spin-dried, and separated by column chromatography (eluent was V 二氯甲烷 :V 甲醇 =100:1), a white solid was obtained with a yield of 20%, m.p.139~141° C., and the structure of the product was determined to be N-((17β)-3-hydroxyl-1,3,5(10 )-estratrien-17-yl)-p-toluamide, its chemical structure is as shown in the following formula:

[0051]

[0052] Among them, R=R 2 =

Embodiment 3

[0054] Synthesis of N-((17β)-3-hydroxy-1,3,5(10)-estratrien-17-yl)-3-phenyl-propionamide:

[0055] Take 150 mg of the second compound 2, dissolve it in 10 mL of dichloromethane, add 1 mL of triethylamine, slowly add 74 uL of 3-phenylpropionyl chloride, follow the reaction by TLC, react at room temperature for 3 h, spin dry under reduced pressure, and extract with ethyl acetate three times. Wash twice with water and once with saturated saline. Dry over anhydrous sodium sulfate, spin dry, and separate by column chromatography (eluent is V 二氯甲烷 :V 甲醇 =100:1), a white solid was obtained. m.p.179-181°C, the structure of the product was determined to be N-((17β)-3-hydroxyl-1,3,5(10)-estratrien-17-yl)-3-benzene by IR, NMR and MS analysis Base-propionamide, its chemical structure is as shown in the following formula:

[0056]

[0057] Among them, R=R 3 =

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Abstract

The invention discloses a 17-amide estrogen compound, the chemical structure of which is shown in the following formula: wherein, R=R 1 =, R 2 = or R 3 =. The 17-amide estrogen compound of the invention has inhibitory effect on ovarian cancer cells, breast cancer cells, human liver cancer cells, human cervical cancer cells and prostate cancer cells, and can be used to prepare antitumor drugs.

Description

technical field [0001] The invention relates to the field of antitumor drugs, in particular to a 17-amide estrogen compound. Background technique [0002] Population growth and population aging, global cancer incidence and mortality are increasing rapidly. In 2018, Dr. Freddie Bray reported in A Cancer Journal for Clinicians (CA), there will be 18.1 million new cancer cases and 9.6 million cancer deaths (Bray F ., Ferlay J., Soerjomataram I., et al. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: A Cancer Journal for Clinicians, 68(6): 394-424.). It is mentioned in the article that the morbidity and mortality of lung cancer are the highest in men, and the morbidity and mortality of breast cancer are the highest in women. It can be seen that finding new anticancer drugs with high efficiency, high selectivity and low toxicity is the direction of drug developers. [0003] The research and development o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J41/00A61K31/568A61P35/00
CPCA61P35/00C07J41/0005
Inventor 甘春芳陈华龙庞婷婷黄晓彤刘钦洲黄燕敏
Owner GUANGXI TEACHERS EDUCATION UNIV
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