Chiral 2,4-disubstituted-thaizolidinone compounds and preparation method and application thereof in preparation of anticancer medicaments

A thiazolone and disubstituted technology, applied in the field of chemical synthesis, can solve problems such as the limitation of thiazole drugs, and achieve the effects of more research, better curative effect and easy research.

Active Publication Date: 2014-01-15
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, research on thiazoles is still limited to achiral and racemic compounds

Method used

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  • Chiral 2,4-disubstituted-thaizolidinone compounds and preparation method and application thereof in preparation of anticancer medicaments
  • Chiral 2,4-disubstituted-thaizolidinone compounds and preparation method and application thereof in preparation of anticancer medicaments
  • Chiral 2,4-disubstituted-thaizolidinone compounds and preparation method and application thereof in preparation of anticancer medicaments

Examples

Experimental program
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Embodiment Construction

[0054] The structure and preparation of the chiral 2,4-disubstituted-thiazolone compounds of the present invention will be further illustrated by specific examples below.

[0055] In Examples 1 to 23, 2,4-disubstituted-thiazolones with different substituents were used as raw materials, and the following preparation methods were used to obtain the corresponding chiral 2,4-disubstituted-thiazolones (DT- 1~DT-23).

[0056] The preparation method of specific chiral 2,4-disubstituted-thiazolone compounds is as follows: 2,4-disubstituted-thiazolone (0.15 mmol, 1.5 eqv) and chiral ligand quinine amine-rosin thiourea (0.01 mmol, 0.1eqv) into a round-bottomed flask equipped with magnetons, add 1mL of methyl tert-butyl ether, cool in an ice bath at 0°C for 10min, then add nitrostyrene (0.1 mmol, 1eqv), at 0°C Stir the reaction, and point the high-efficiency plate to detect the completion of the reaction (6-12h). The reaction solution was concentrated and purified by silica gel column ...

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Abstract

The invention discloses chiral 2,4-disubstituted-thaizolidinone compounds with anticancer activity. The compounds have the following structural formula, wherein R1 is substituted or un-substituted aryl; R2 is isopropyl, isobutyl or tert-butyl; and R3 is ethyl or benzyl. Classical in vivo and in vitro experiments prove that the chiral 2,4-disubstituted-thaizolidinone compounds have proliferation inhibiting effect on various cancers such as breast cancer, bladder cancer, prostate cancer and cervical cancer.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a class of chiral 2,4-disubstituted-thiazolone compounds and a preparation method thereof; the invention also relates to the application of such chiral compounds in the preparation of anticancer drugs. Background technique [0002] Chiral drugs are composed of chiral compounds with pharmacological activity, which play a therapeutic role in the human body through chiral matching and molecular recognition with biological macromolecules. Although the physical and chemical properties of enantiomeric drugs are basically the same in vitro, because the receptors or targets that drug molecules act on are chiral proteins and nucleic acid macromolecules composed of amino acids, nucleosides, membranes, etc., they There are certain requirements for the three-dimensional configuration of the drug molecules bound to it. Therefore, enantiomer drugs often show great differences in phar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/36C07D409/06A61K31/427A61K31/426A61P35/00
Inventor 王锐刘晓东宋虹瑾
Owner LANZHOU UNIVERSITY
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