Hydroxamic acid compounds and application thereof in preparation of medicines for inhibiting cancer cell proliferation and/or treating cancers

The technology of a compound and hydroxamic acid is applied in the field of hydroxamic acid compounds and their application in the preparation of drugs for inhibiting cancer cell proliferation and/or treating cancer, and can solve the problem that condensing agents and adjuvants are expensive and unreachable. effects, environmental pollution, etc.

Active Publication Date: 2014-07-16
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent application (publication number CN103159646A) discloses that a compound N-(2,5-dimethoxyphenyl)-N'-hydroxysuberamide has the effect of inhibiting the proliferation of various cancer cells, but failed to achieve better effect
The condensing agent and auxiliary agent described in the article are not only expensive, but also produ

Method used

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  • Hydroxamic acid compounds and application thereof in preparation of medicines for inhibiting cancer cell proliferation and/or treating cancers
  • Hydroxamic acid compounds and application thereof in preparation of medicines for inhibiting cancer cell proliferation and/or treating cancers
  • Hydroxamic acid compounds and application thereof in preparation of medicines for inhibiting cancer cell proliferation and/or treating cancers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of N-(3,4-dimethylphenyl)-N'-hydroxysuberamide (abbreviated as B113).

[0052] Step (1): Weigh 1.21g (10mmol) of 3,4-dimethylaniline, 1.88g (10mmol) of monomethyl suberate, and 0.31g (5mmol) of boric acid into a 100ml three-neck round bottom flask, and add 30ml of toluene , nitrogen protection, magnetic stirring, heating the oil bath to toluene reflux, using a water separator to separate the water generated in the reaction process, filling the water separator with toluene before the reaction, the reaction time is 10h, and tracking with a thin layer chromatography plate during the reaction For the reaction, the developer is ethyl acetate:petroleum ether=1:1. After the reaction is completed, pour the reaction solution into 300ml of petroleum ether under stirring. After stirring for 0.5h, vacuum filter the solid with a sand core funnel, and wash the solid with water to remove the catalyst boric acid, and then wash it with petroleum ether after draining. solid ...

Embodiment 2

[0055] Preparation of N-(3-chloro-4-fluorophenyl)-N'-hydroxysuberamide (hydroxamic acid) (referred to as B115).

[0056] Step (1): Weigh 1.46g (10mmol) of 3-chloro-4-fluoroaniline, 1.88g (10mmol) of monomethyl suberate, and 0.31g (5mmol) of boric acid into a 100ml three-neck round bottom flask, and add 30ml of toluene , nitrogen protection, magnetic stirring, heating the oil bath to toluene reflux, using a water separator to separate the water generated during the reaction, filling the water separator with toluene before the reaction, the reaction time is 12h, and tracking with a thin layer chromatography plate during the reaction For the reaction, the developer is ether:petroleum ether=1:1. After the reaction is completed, pour the reaction solution into 300ml of petroleum ether under stirring. After stirring for 0.5h, vacuum filter the solid with a sand core funnel, and wash the solid with water to remove the catalyst boric acid, and then wash it with petroleum ether after d...

Embodiment 3

[0059] Preparation of N-(3-bromo-5-trifluoromethylphenyl)-N'-hydroxysuberamide (referred to as B123).

[0060] Step (1): Weigh 0.8g (3.33mmol) of 3-bromo-5-trifluoromethylaniline, 0.63g (3.33mmol) of monomethyl suberate, and 0.10g (1.67mmol) of boric acid in a 100ml three-port circle Bottom flask, add 30ml toluene, nitrogen protection, magnetic stirring, oil bath heating to toluene reflux, use water separator to separate the water generated in the reaction process, before the reaction, the water separator is filled with toluene, the reaction time is 20h, during the period use The reaction was followed by thin-layer chromatography, and the developing solvent was ether:petroleum ether=1:1. After the reaction is completed, pour the reaction solution into 300ml of petroleum ether under stirring. After stirring for 0.5h, vacuum filter the solid with a sand core funnel, and wash the solid with water to remove the catalyst boric acid, and then wash it with petroleum ether after drain...

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Abstract

The invention relates to the field of medicinal chemistry and particularly relates to hydroxamic acid compounds and application thereof in preparation of medicines for inhibiting cancer cell proliferation and/or treating cancers. The hydroxamic acid compounds provided by the invention is capable of inhibiting cancer cell proliferation so as to treat cancers and especially has excellent activity of inhibiting proliferation of melanoma cell (A375), human lung cancer cell (A549), human gastric carcinoma cell (MGC80-3), human esophageal carcinoma cell (TE-1) and cell hepatoma carcinoma cell (HepG2).

Description

technical field [0001] The invention relates to a class of hydroxamic acid compounds and a preparation method and use thereof. Background technique [0002] Histone deacetylase (HDAC) and histone acetyltransferase (HAT) are a class of mutually antagonistic proteases that widely exist in eukaryotic cells, and they jointly regulate the terminal amino acid residues of histones acetylation, so that it is in a state of equilibrium. The acetylation and deacetylation of histones is a way to regulate gene transcription. The degree of acetylation of histones affects the expression of genes by affecting the structure of chromatin. The acetylation status of histones is diverse, and specific gene sites are acetylated in a site-specific manner. The occurrence of tumors is closely related to the imbalance of acetylation and deacetylation of lysine residues at the nitrogen end of nucleosome core histones. Histone deacetylase and histone acetyltransferase jointly control the acetylation o...

Claims

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Application Information

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IPC IPC(8): C07C259/06A61K31/167A61P35/00
CPCA61K31/167C07C259/06
Inventor 袁其朋邓炳华谢瑞武新颖屈悦杨明
Owner BEIJING UNIV OF CHEM TECH
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