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Derivative of multi-target antitumor inhibitor 2-aminopyrrole-triazine and synthesis method thereof

An anti-tumor and inhibitor technology, applied in the field of cancer cells, can solve the problems of limited clinical application, toxic and side effects, etc., and achieve the effect of strong therapeutic effect, small side effects and high affinity

Inactive Publication Date: 2011-08-17
青岛佳诺华医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing inhibitors have strong toxic and side effects, which limits their clinical application.

Method used

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  • Derivative of multi-target antitumor inhibitor 2-aminopyrrole-triazine and synthesis method thereof
  • Derivative of multi-target antitumor inhibitor 2-aminopyrrole-triazine and synthesis method thereof
  • Derivative of multi-target antitumor inhibitor 2-aminopyrrole-triazine and synthesis method thereof

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Embodiment Construction

[0051] 1. Synthesis method:

[0052] The raw materials used in the present invention all come from market sales.

[0053] Hereinafter "DMF" is dimethylformamide, "DMAP" is dimethylaminopyridine, "TBME" is methyl tert-butyl ether, "Me" is methyl, "TEA" is triethylamine, " "i-PrOH" is isopropanol, "DMSO" is dimethylsulfone, "DCM" is dichloromethane, "TLC" is thin-layer chromatography, and "MTBE" is methyl tert-butyl ether.

[0054] The following reaction steps illustrate a synthetic route of the present invention:

[0055]

[0056]

[0057] Specific instructions for each reaction step:

[0058] 1. Synthetic method of 1H-pyrrole-2,4 dicarboxylic acid (2) of compound diethyl ester:

[0059] First (4.56 g, 40 mmol) ethyl isocyanoacetate (1) and (9.2 g, 60 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were dissolved in 200 ml of tetrahydrofuran to form a solution, then add 80mmol of p-formaldehyde to the solution, and place the reaction mixture in an environment of 50±0.5...

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Abstract

The invention discloses a derivative of a multi-target antitumor inhibitor, namely 2-aminopyrrole-triazine and a synthesis method thereof, and relates to the technical field of the treatment of abnormal cells in mammals. The derivative is synthesized by taking ethyl isocyanoacetate as a starting point through a chemical synthesis method, and has the advantages of mature process, short production period, environment friendliness, low cost and the like. The product can be used as a heat shock protein (Hsp) 90 multi-target antitumor inhibitor, can inhibit Hsp90, and promote the degradation of Hsp90 effect proteins which play an important role in tumor growth signal pathways through ubiquitination, so that multiple targets of the tumor growth signal pathways are blocked and the growth of tumor is effectively prevented. The derivative has higher affinity with tumor cells, can selectively kill the tumor cells, and promote the degradation of primer proteins thereof through ubiquitin-proteasome pathways, so that the effects of tumor treatment and resistance of the targets are achieved, and the derivative has strong action and small side effect.

Description

technical field [0001] The invention relates to the technical field of treating abnormal cells in mammals, especially cancer cells. Background technique [0002] Heat shock proteins (heat shock proteins, Hsps) were discovered in 1962 by geneticist Ritossa. This is a kind of protein that is highly conserved in the process of biological evolution and widely exists in prokaryotes and eukaryotes. Hsp is a multi-gene family, in which the products of different genes have different expressions, functions and localizations in cells. In the art, members of this family are often distinguished by differences in molecular weight, such as Hsp90, Hsp70, and Hsp27. In addition, there are some heat shock proteins classified by related glycoproteins, such as GRP 94 and GRP 75. As molecular chaperones in the body, Hsps are involved in maintaining the normal folding of proteins to form the normal structure of proteins, and play an important role in regulating the balance of protein synthesi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/53A61P35/00
Inventor 孟佳伦
Owner 青岛佳诺华医药科技有限公司
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