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Preparation method and application of N-substituted hydroxamic acid compound

A technology of a compound and a target compound, applied in the field of preparation and use of N-substituted hydroxamic acid compounds

Inactive Publication Date: 2013-09-25
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] There are many reasons for the occurrence of tumors. In the past, gene mutations were believed to lead to the formation of tumors, and many tumor suppressor genes and oncogenes were successfully discovered. presents new challenges, such as changes in the phenotype of an organism without a change in the base sequence of the DNA

Method used

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  • Preparation method and application of N-substituted hydroxamic acid compound
  • Preparation method and application of N-substituted hydroxamic acid compound
  • Preparation method and application of N-substituted hydroxamic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Preparation of N-hydroxyl-N-phenyl-4-benzamido-benzamide I a (1)

[0050] Weigh 3g (20mmol) of methyl 4-aminobenzoate and dissolve it in 40ml of anhydrous tetrahydrofuran, add 30mmol of sodium bicarbonate, add dropwise 20ml of anhydrous tetrahydrofuran solution containing 20mmol of benzoyl chloride, stir at room temperature for 4 hours, filter, and depressurize Distill to obtain white solid 4-benzamidomethyl benzoate; dissolve with 50ml THF, add 15mmol 4-benzamidomethylbenzoate, add 30ml of 1mol / L sodium hydroxide solution, heat to reflux for 5 hours, depressurize Part of the solvent was evaporated, slowly poured into 100ml of an aqueous solution dissolved with 30mmol of hydrochloric acid, filtered and dried to obtain compound 4-benzamidobenzoic acid; 15mmol of compound 4-benzamidobenzoic acid was dissolved in 40ml of anhydrous tetrahydrofuran, and 4 drops of DMF, add 18 mmol of oxalyl chloride dropwise in an ice-water bath, stir at room temperature for 4 hour...

Embodiment 2

[0053] Example 2 Preparation of N-hydroxy-N-o-methylphenyl-4-benzamido-benzamide Ia (2)

[0054] Preparation method: replace the nitrogen phenyl hydroxylamine in Example 1 with N-(2-methylphenyl) hydroxylamine, and the other preparation methods are the same as in Example 1. The product is a white solid, and the structural formula is shown in formula 6,

[0055]

[0056] Yield 37.6%, mp 236.2-238.4?C.; 1 HNMR (400MHz DMSO-d 6 ): δ 10.47(s, 1H), 9.84(s, 1H), 8.06-7.95(m, 4H), 7.87-7.81(m, 2H), 7.64-7.52(m, 4H), 7.36-7.9515(m, 4H), 2.26(s, 3H).; 13 CNMR (100MHz DMSO-d 6 ): Δ 165.7, 164.7, 141.4, 141.0, 136.5, 134.6, 133.6, 131.7, 130.2, 129.6, 129.2, 127.7, 126.5, 125.9, 119.4, 17.9.; , found 347.1381..

Embodiment 3

[0057] Example 3 Preparation of N-hydroxyl-N-m-methylphenyl-4-benzamido-benzamide Ia (3)

[0058] Preparation method: replace the nitrogen phenyl hydroxylamine in Example 1 with N-(3-methylphenyl) hydroxylamine, and the other preparation methods are the same as in Example 1. The product is a white solid, and the structural formula is shown in formula 7,

[0059]

[0060] Yield 44.3%, mp 233.9-235.1?C.; 1 HNMR (400MHz DMSO-d 6 ): δ 10.67(s, 1H), 10.46(s, 1H), 7.97(d, J = 7.2 Hz, 2H), 7.84(d, J = 8.4Hz, 2H), 7.69-7.53(m, 5H), 7.40(s, 1H), 7.34-7.24(m, 2H), 7.02(d, J = 7.2 Hz, 1H), 2.32(s, 3H).; 13 CNMR (100MHz DMSO-d 6 ): Δ 167.4, 165.8, 142.3, 141.0, 137.8, 134.7, 131.8, 130.2, 129.4, 127.9, 127.6, 126.1, 119.5, 119.2, 21.1.; , found 347.1383..

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Abstract

The invention discloses a preparation method and application of an N-substituted hydroxamic acid compound. The histone compound with a 4-benzamido-N-hydroxy-N-benzoylphenyl ammonia structure, i.e., the N-substituted hydroxamic acid compound, is represented by formula 1 as described in the specification. The preparation method comprises the following steps: with methyl p-aminobenzoate, benzoyl chloride and nitrobenzene as raw materials, allowing methyl p-aminobenzoate and benzoyl chloride to undergo aminoacylation and subjecting a reaction product to hydrolysis and acylation so as to prepare 4-benzamido-benzoyl chloride or 4-(4-chlorphenyl-formamido)benzoyl chloride or 4-phenylacetamido-benzoyl chloride; and reducing nitrobenzene into N-hydroxy aniline under the catalysis of Raney nickel and reacting N-hydroxy aniline with 4-benzamido-benzoyl chloride so as to obtain the target compound.

Description

technical field [0001] The invention relates to a preparation method and application of N-substituted hydroxamic acid compounds. Specifically, the present invention is a histone deacetylase inhibitor with 4-benzamido-N-hydroxyl-N-phenylbenzamide structure, and the use and preparation method of this kind of compound. Background technique [0002] There are many reasons for the occurrence of tumors. In the past, gene mutations were believed to lead to the formation of tumors, and many tumor suppressor genes and oncogenes were successfully discovered. New challenges are presented, such as the altered phenotype of an organism without a change in the base sequence of the DNA. In order to clarify the reasons for these phenomena, the hypothesis of epigenetic modification has been put forward in recent years. This theory mainly involves two aspects: one is the reversible modification of histones in cell chromatin [1-3] , the other is the reversible modification of methylation for ...

Claims

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Application Information

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IPC IPC(8): C07C259/10A61K31/167A61P35/00
Inventor 贺殿郭青欣马尚贤侯猛
Owner LANZHOU UNIVERSITY
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