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Olefinated estrogen compound as well as preparation and application thereof

An estrogen and compound technology, applied in the field of olefinic estrogen compounds and their preparation, can solve the problems of low yield and the like, and achieve the effects of excellent inhibitory activity, novel structure and good antitumor activity

Active Publication Date: 2019-04-05
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This requires long steps and strict conditions, and the yield is very low, so the simple re-modification of estrogen anti-tumor drugs has become a new research direction for pharmaceutical experts

Method used

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  • Olefinated estrogen compound as well as preparation and application thereof
  • Olefinated estrogen compound as well as preparation and application thereof
  • Olefinated estrogen compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: Preparation of olefinated estrogenone

[0022] Add 1mmol estrone (II-1) to 4ml of acetic acid solvent, add 0.2mmol palladium acetylacetonate, 1.2mmol ethyl acrylate, 2.0mmol silver acetate, 2.0mmol potassium persulfate, and react at 80°C for 12 hours. After the reaction was completed, a saturated NaCl aqueous solution was added to the reaction liquid, extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain a crude compound. The crude compound was subjected to silica gel column chromatography, using a solution of ethyl acetate and petroleum ether with a volume ratio of 1:8 as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC, and the collected eluent was passed through The solvent was removed under reduced pressure and dried to obtain 37 mg of a pure compound represented by formula (I-1).

[0023] Formula (I-1)...

Embodiment 2

[0025] Embodiment 2: Preparation of olefinated estradiol

[0026] Add 1mmol estradiol (II-2) to 4ml of acetic acid solvent, add 0.2mmol palladium acetylacetonate, 1.2mmol ethyl acrylate, 2.0mmol silver acetate, 2.0mmol potassium persulfate, and react at 80°C for 12 hours. After the reaction was completed, a saturated NaCl aqueous solution was added to the reaction liquid, extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain the crude compound (I-2). The crude compound (I-2) was subjected to silica gel column chromatography, using a solution with a volume ratio of ethyl acetate and petroleum ether of 1:5 as the mobile phase, followed by TLC to collect the eluent with an Rf value of 0.3-0.5, and obtained The eluate was desolventized under reduced pressure and dried to obtain 29 mg of pure compound represented by formula (I-2).

[0027] NMR data of the compound of formula (...

Embodiment 3

[0029] Embodiment 3: Preparation of olefinated estynol

[0030] Add 1mmol estynol (II-3) to 4ml of acetic acid solvent, add 0.2mmol palladium acetylacetonate, 1.2mmol ethyl acrylate, 2.0mmol silver acetate, 2.0mmol potassium persulfate, react at 80°C for 12 hours, After the reaction, a saturated NaCl aqueous solution was added to the reaction liquid, extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain the crude compound (I-3). The crude compound (I-3) was subjected to silica gel column chromatography, and a solution with a volume ratio of ethyl acetate and petroleum ether of 1:5 was used as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC to obtain The eluate was desolventized under reduced pressure and dried to obtain 29 mg of pure compound represented by formula (I-3).

[0031] NMR data of the compound of formula (I-3): 1H ...

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Abstract

The invention relates to an olefinated estrogen compound (I), a preparation method thereof and application thereof to the preparation of an antineoplastic drug. The invention has the beneficial effects which are mainly embodied in that (1), an olefinated estrogen drug provided by the invention is novel in structure, has favorable antineoplastic activity, and particularly has excellent inhibitory activity to the cell line MCF-7 of a mammary cancer and a cell line PC-7 of a prostatic cancer; and (2), a preparation method of the olefinated estrogen drug, which is provided by the invention, can beused for preparing and obtaining the olefinated estrogen drug in a high-yield manner by only needing one step, and has the characteristics of being simple, efficient, convenient and quick, and the like.

Description

(1) Technical field [0001] The invention relates to an olefinated estrogen compound, a preparation method thereof, and an application thereof in the preparation of antitumor drugs. (2) Background technology [0002] Endocrine disorders can induce various diseases, such as breast cancer, cervical cancer, prostate cancer, endometrial cancer, polycystic ovarian syndrome and various menopausal symptoms, among which estrogen imbalance is the main factor. At present, estrogen-dependent cancer has also become a major disease that threatens the safety of human life. It has the common characteristics of malignant tumors such as fast growth, easy transfer, difficult to cure, and high lethality. At present, there are many drugs for regulating estrogen, and estrone and estradiol are two commonly used ones, which are mainly used for the treatment of breast cancer, prostate cancer and endometrial cancer, etc. They mainly down-regulate estrogen by mediating MAPK signaling pathway. Hormone...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00A61P35/00
CPCA61P35/00C07J1/0051C07J1/0059C07J1/0066C07J1/0096
Inventor 朱勍窦言东刘江
Owner ZHEJIANG UNIV OF TECH
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