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Olefinated ethinyloestradiol compound, and preparation and application thereof

A compound, the technology of ethinyl estradiol, which is applied in the fields of olefinated ethinyl estradiol compounds and its preparation and application, can solve the long-term, high morbidity and mortality of diseases, and the correlation between occurrence and progress has not been well understood. Interpretation and other issues to achieve the effect of novel structure, excellent inhibitory activity, and good antitumor activity

Inactive Publication Date: 2019-11-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it takes a long time to regulate the occurrence and progression of diseases by blocking signaling pathways and involves many factors, so there is a greater risk
[0005] Several drugs have been developed against breast cancer, but the morbidity and mortality of the disease are so high and the relationship of these steroid sex hormones to the development and progression of the disease is still not well explained

Method used

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  • Olefinated ethinyloestradiol compound, and preparation and application thereof
  • Olefinated ethinyloestradiol compound, and preparation and application thereof
  • Olefinated ethinyloestradiol compound, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Preparation of 2-iodoethinyl estradiol intermediate

[0040]

[0041]Add 0.2 mmol of ethinyl estradiol (EE) to a 25 mL round bottom flask, then add 5 mL of acetonitrile solvent to dissolve, add 0.01 mmol (1 equiv) of indium trifluoromethanesulfonate, and 0.11 mmol of N-iodosuccinimide mmol (11 equiv), the reaction was stirred at room temperature for 8-10 h, and the reaction process was monitored by a TLC plate. After the reaction is over, add about 15 mL of saturated aqueous sodium chloride solution to the reaction solution, extract with dichloromethane, take the organic layer, dry it over anhydrous sodium sulfate, filter, and remove the organic solvent under reduced pressure with a rotary evaporator to obtain monoiodo Crude EEI compound. The crude product of the EEI compound was subjected to silica gel column chromatography, using a solution with a volume ratio of ethyl acetate and petroleum ether of 1:3 as the mobile phase, followed by TLC to collect...

Embodiment 2

[0043] Embodiment 2: Preparation 2,4-diiodoethinyl estradiol intermediate

[0044]

[0045] Add ethinyl estradiol (EE) 0.3mmol in the 25mL round-bottomed flask, then add 10mL of absolute ethanol to dissolve, add iodine simple substance 0.15mmol (0.5equiv), 30% hydrogen peroxide 0.6mmol (2equiv), 50 The reaction was stirred at ℃ for 10-12 h, and the reaction process was monitored with a TLC plate. After the reaction was completed, 20 mL of saturated aqueous sodium chloride solution was added to the reaction liquid, extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, filtered, and the organic solvent was removed by a rotary evaporator under reduced pressure to obtain a crude product of EII compound. Put the EII compound crude product into silica gel column chromatography, use ethyl acetate and petroleum ether as the mobile phase with a volume ratio of 1:3, TLC tracking and collecting the eluent with an Rf value of 0.3-0.6, and collect th...

Embodiment 3

[0047] Example 3: Preparation of ethinyl estradiol modified drug EEX-1

[0048]

[0049] Weigh compound (Example 1) EEI 0.4mmol and add 10mL of N,N-dimethylformamide solvent, add 0.48mmol (1.2equiv) ethyl acrylate, 0.04mmol (0.1equiv) palladium acetate, 0.8mmol (2equiv) triethylamine, under anhydrous and oxygen-free conditions, stirred and reacted at 90°C for 4-8h at high temperature. After the reaction, 30mL of saturated aqueous sodium chloride solution was added to the reaction solution, and extracted three times with dichloromethane, and the organic The phase was dried with anhydrous sodium sulfate, filtered, rotary evaporated under reduced pressure, and vacuumized to obtain the crude product of EEX-1 compound. The crude product of the EEX-1 compound was subjected to silica gel column chromatography, using a solution with a volume ratio of ethyl acetate and petroleum ether of 1:12 as the mobile phase, and followed by TLC to collect the eluent with an Rf value of 0.4-0.5,...

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Abstract

The invention relates to an olefinated ethinyloestradiol compound with good anti-tumor activity, and a preparation method and application thereof. The olefinated ethinyloestradiol compound has the beneficial effects mainly shown in that (1) an ethinyloestradiol drug with modified different sites is novel in structure, has the good anti-tumor activity, and has excellent inhibitory activity especially for a human prostate cancer cell line PC-3 and breast cancer cells MCF-7; and (2) the most suitable olefination modification sites of the ethinyloestradiol drug are provided through screening, andthe foundation is laid for modification of the ethinyloestradiol drug.

Description

[0001] (1) Technical field [0002] The invention relates to olefinated ethinyl estradiol compounds and their preparation and application. [0003] (2) Background technology [0004] In September 2018, the International Agency for Research on Cancer (IARC), a subsidiary of the World Health Organization, released the latest global cancer statistics "Global Cancer Report" in September 2018, providing information on the incidence and mortality of 36 cancers in 185 countries and regions around the world. data. In 2018, there were 18.1 million new cancer cases worldwide (9.5 million men, 8.6 million women), and 9.6 million deaths (5.4 million men, 4.2 million women), further increasing the global cancer burden. Worldwide, 1 / 5 men and 1 / 6 women will suffer from cancer, and 1 / 8 men and 1 / 11 women will die from it. The five-year survival rate, that is, the number of people who are still alive after 5 years of illness, is estimated to reach 43.8 million. The incidence and mortality o...

Claims

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Application Information

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IPC IPC(8): C07J1/00A61K31/567A61P35/00
CPCA61P35/00C07J1/0096
Inventor 朱勍瞿姣姣顾晓旭
Owner ZHEJIANG UNIV OF TECH
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