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Cysteine derivative, synthesis method and application thereof

A technology of cysteine ​​and synthesis method, which is applied to cysteine ​​derivatives and their synthesis, and the application field of histone deacetylase inhibitors in the preparation of antitumor drugs, which can solve weak therapeutic effects and limit applications. and other problems, to achieve the obvious effect of anti-tumor activity

Active Publication Date: 2021-08-24
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although most HDAC inhibitors, including clinically and listed above, have shown effective anticancer activity, they are usually limited to the treatment of hematological tumors (such as skin T-cell lymphoma, peripheral T-cell lymphoma, etc.) Tumors (e.g. lung, breast, etc.) tend to show weak therapeutic effects, which severely limits their application in cancer therapy

Method used

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  • Cysteine derivative, synthesis method and application thereof
  • Cysteine derivative, synthesis method and application thereof
  • Cysteine derivative, synthesis method and application thereof

Examples

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Embodiment 1

[0031] The concrete synthetic method of formula (I) compound, comprises the following steps:

[0032] S1. Take N-((benzyloxy)carbonyl)-S-(4-(tert-butoxy)-4-oxobutyl)-L-cysteine ​​and dry THF (tetrahydrofuran) after stirring and dissolving Add DIEA (N,N-diisopropylethylamine), stir for 5-8 minutes, add HBTU (O-benzotriazole-tetramethyluronium hexafluorophosphate), add aniline after 15-20 minutes, and react at room temperature 3-3.5h; the obtained product was evaporated to remove the solvent under reduced pressure, added dichloromethane to dissolve, then washed the organic layer with HCl solution and saturated NaCl solution, collected the organic layer, dried over anhydrous Na2SO4, concentrated the organic layer, and finally passed through a silica gel column Purified by chromatography to obtain a light yellow solid;

[0033] Wherein, the molar ratio of each raw material to the catalyst is N-((benzyloxy)carbonyl)-S-(4-(tert-butoxy)-4-oxobutyl)-L-cysteine: DIEA: HBTU:aniline=1:...

Embodiment 2

[0048] The specific synthetic method of the compound of formula (I) differs from Example 1 in that in S1, the N-((benzyloxy)carbonyl)-S-(4-(tert-butoxy)-4-oxobutane base)-L-cysteine, the N,N-diisopropylethylamine, the O-benzotriazole-tetramethyluronium hexafluorophosphate and the molar ratio of the aniline is 1 :4:1.5:2.

Embodiment 3

[0050] The specific synthetic method of the compound of formula (I) differs from Example 1 in that in S1, the N-((benzyloxy)carbonyl)-S-(4-(tert-butoxy)-4-oxobutane base)-L-cysteine, the N,N-diisopropylethylamine, the O-benzotriazole-tetramethyluronium hexafluorophosphate and the molar ratio of the aniline is 1 :4:3:2.

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Abstract

The invention relates to the technical field of antitumor drugs, in particular to a cysteine derivative, a synthesis method thereof and application of the cysteine derivative as a histone deacetylase inhibitor in preparation of antitumor drugs. The cysteine derivative has a potential inhibition effect on HDAC, and can obviously inhibit HDAC in vivo and in vitro so as to generate antitumor activity. The synthesis raw materials are relatively cheap, the cost is relatively low, and the derivative is expected to become a novel HDAC inhibitor anti-tumor drug for efficiently inhibiting HDAC.

Description

technical field [0001] The invention relates to the technical field of anti-tumor drugs, in particular to a cysteine ​​derivative and its synthesis method, and its application as a histone deacetylase inhibitor in the preparation of anti-tumor drugs. Background technique [0002] Histone deacetylase (HDAC) inhibitors have been clinically used in the treatment of tumor diseases, and have shown good prospects for clinical application. The main effect of HDAC inhibitors on tumor cells is to inhibit tumor cell proliferation, induce cell cycle arrest, induce tumor cell apoptosis, and inhibit the formation of tumor new blood vessels. As a new class of antitumor drugs, HDAC inhibitors have very important research and development value. [0003] At present, HDAC inhibitors can be divided into: hydroxamic acid (such as SAHA), cyclotetrapeptides with epoxy ketone structure (such as trapoxinA), benzamides (such as M S-275), cyclic peptides without epoxy ketone structure, short chain ...

Claims

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Application Information

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IPC IPC(8): C07C323/60C07C319/20A61P35/02A61P35/00
CPCC07C323/60A61P35/02A61P35/00Y02P20/55
Inventor 何彬王洁曹灼贤李燕赵永龙刘亭李勇军
Owner GUIZHOU MEDICAL UNIV
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