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Dehydroepiandrosterone D cyclobenzo-aminothiazole ring compounds as well as preparation method and application thereof

A technology for dehydroepiandrosterone and compounds, which is applied in the directions of steroids, organic chemistry, drug combinations, etc., to achieve the effect of a simple synthesis method

Active Publication Date: 2013-07-10
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Using the principle of active fragment integration, the thiazole structural unit was introduced into the steroid core to synthesize a new class of dehydroepiandrosterone D-cyclothiazole ring imines and imine reduction compounds, and their biological activities were initially evaluated , there is no literature report

Method used

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  • Dehydroepiandrosterone D cyclobenzo-aminothiazole ring compounds as well as preparation method and application thereof
  • Dehydroepiandrosterone D cyclobenzo-aminothiazole ring compounds as well as preparation method and application thereof
  • Dehydroepiandrosterone D cyclobenzo-aminothiazole ring compounds as well as preparation method and application thereof

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Embodiment

[0035] 1. 16-bromo dehydroepiandrosterone 11 Synthesis

[0036]

[0037] Dissolve dehydroepiandrosterone (0.01mol) in 100mL of methanol, add copper bromide (0.02mmol) and react at room temperature for 10 hours. After the reaction is complete, evaporate the system to dryness, extract with dichloromethane and wash with water and saturated saline for 2 hours respectively. Second, the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to obtain a light yellow solid 11 in quantitative yield without purification. 1H NMR (400 MHz, CDCl3) δ 5.37(d, 1H, J=5.42 Hz, 6-H), 4.54(t, 1H, 16-H), 3.54(m, 1H, 3α-H), 1.04(s , 3H, 18-Me), 0.93(s, 3H, 19-Me).

[0038] 2. Dehydroepiandrosterone D-cyclothiazole amino compound 12 Synthesis

[0039]

[0040] Compound 11 (3.4g, 9.26 mmol), thiourea (3.4g, 44.7mmol) and triethylamine (3.4g, 33.6mmol) were dissolved in 150mL ethanol and refluxed for 10h, and white solid appeared in the reaction system as the reactio...

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Abstract

The invention belongs to the field of medicinal chemistry and in particular relates to dehydroepiandrosterone D cyclobenzo-aminothiazole ring imine and imine reducing compounds as well as a preparation method and application thereof. The compounds are shown in a formula I in the specification. An in-vitro antineoplastic activity experiment indicates that the compounds have better broad-spectrum antineoplastic activity, have a favorable inhibition effect on multiple human cancer cells, such as EC109 and EC9706 and are suitable for research of antineoplastic lead compounds or preparation of novel antineoplastic medicaments. The preparation method is simple and convenient and suitable for industrial production.

Description

technical field [0001] The invention relates to a class of dehydroepiandrosterone D-cyclothiazole cyclic imines and imine reduction compounds with anti-tumor activity, a synthesis method and an anti-tumor application thereof, belonging to the field of medicinal chemistry. Background technique [0002] According to the statistics of the World Health Organization, cancer is a major cause of death worldwide, and the number of deaths from cancer worldwide is increasing year by year. It is estimated that by 2030, the number of global cancer deaths will increase by 45%. However, due to the shortcomings of existing anti-tumor drugs such as high toxicity and side effects and drug resistance, it has become a very important and urgent subject to study new anti-tumor drugs with high efficiency, low toxicity and no resistance to existing anti-tumor drugs. [0003] As a class of cyclopentane polyhydrophenanthrene compounds, steroids are ubiquitously present in animal and plant tissues, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61K31/58A61P35/00
Inventor 刘宏民张宝乐张恩郑甲信庞露苹李亚飞
Owner ZHENGZHOU UNIV
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