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Amidoxime compound and application thereof to preparation of medicines for inhibiting cancer cell proliferation

A compound, amidoxime technology, applied in the field of amidoxime compounds and their application in the preparation of drugs for inhibiting cancer cell proliferation

Active Publication Date: 2017-06-13
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are currently no drugs on the market for amidoxime compounds. Therefore, exploring amidoxime compounds as effective histone-specific sirtuin 1 inhibitors is an important scientific research project for workers in this field

Method used

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  • Amidoxime compound and application thereof to preparation of medicines for inhibiting cancer cell proliferation
  • Amidoxime compound and application thereof to preparation of medicines for inhibiting cancer cell proliferation
  • Amidoxime compound and application thereof to preparation of medicines for inhibiting cancer cell proliferation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Amidoxime Compound Example 1: [Compound 101]

[0044] (Z)-2-((3-Ethyl-7-methoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)thio)-N'-hydroxyacetimide Amide

[0045]Step (1): Weigh 1.20g (7.2mmol) of 2-amino-4-methoxybenzoic acid, 0.63g (7.2mmol) of ethyl isothiocyanate, and 2.4ml of triethylamine in 100ml three-hole round bottom Add 35ml of ethanol to the flask, under nitrogen protection, magnetic stirring, and heat the oil bath until the ethanol refluxes. The reaction time is 2h. During this period, the reaction is followed by thin-layer chromatography. The developer is petroleum ether: ethyl acetate = 2:1. After the reaction is completed, cool to room temperature, vacuum filter the solid with a sand core funnel, wash the solid with ice ethanol, and then use petroleum ether to wash the solid and drain the solid. Finally a clean solid is obtained;

[0046] Step (2): Weigh 1g (4.23mmol) of the product obtained in the first step reaction, 0.66g (5.5mmol) of bromoacetonitrile, 1...

Embodiment 2

[0048] Amidoxime Example 2: [Compound 109]

[0049] (Z) 7-((3-ethyl-7-fluoro-4-oxo-3,4-dihydro-quinazolin-2-yl)sulfanyl)-N'-hydroxyheptanimide amide preparation.

[0050] Step (1): Weigh 1.55g (10mmol) of 2-amino-4-fluorobenzoic acid, 0.87g (10mmol) of ethyl isothiocyanate, and 3.10ml of triethylamine in a 100ml three-necked round-bottomed flask, and add 35ml of ethanol , nitrogen protection, magnetic stirring, the oil bath was heated to ethanol reflux, the reaction time was 2h, during which the reaction was followed by thin-layer chromatography, and the developer was petroleum ether: ethyl acetate = 2:1. After the reaction is completed, cool to room temperature, vacuum filter the solid with a sand core funnel, wash the solid with ice ethanol, and then use petroleum ether to wash the solid and drain the solid. Finally a clean solid is obtained;

[0051] Step (2): Weigh 1g (4.46mmol) of the product obtained in the first step reaction, 1.10g (5.80mmol) of bromoheptanitrile,...

Embodiment 3

[0053] Hydroxamic Acid Example 3: [Compound 113]

[0054] (Z) 7-((3-ethyl-7-fluoro-4-oxo-3,4-dihydro-quinazolin-2-yl)sulfanyl)-N'-hydroxyheptanimide amide preparation.

[0055] Step (1): Weigh 3.00g (17.50mmol) of 2-amino-4-chlorobenzoic acid, 1.50g (17.50mmol) of ethyl isothiocyanate, and 6.0ml of triethylamine in a 100ml three-necked round-bottomed flask, and add 35ml of ethanol, nitrogen protection, magnetic stirring, oil bath heating to ethanol reflux, the reaction time is 2h, during which the reaction is followed by thin-layer chromatography, the developer is petroleum ether: ethyl acetate = 2:1. After the reaction is completed, cool to room temperature, vacuum filter the solid with a sand core funnel, wash the solid with ice ethanol, and then use petroleum ether to wash the solid and drain the solid. Finally a clean solid is obtained;

[0056] Step (2): Weigh 1g (4.15mmol) of the product obtained in the first step of the reaction, 1.03g (5.40mmol) of bromoheptanitri...

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PUM

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Abstract

The invention discloses an amidoxime compound and application thereof to preparation of medicines for inhibiting cancer cell proliferation, and relates to the field of medicinal chemistry. The amidoxime compound provided by the invention has capacity of inhibiting the cancer cell proliferation, so that an aim of treating cancers is achieved. The amidoxime compound particularly has excellent activity of inhibiting the cancer cell proliferation of human cutaneous melanoma cells (A375), human lung cancer cells (A549), human gastric carcinoma cells (MGC80-3), and human hepatoma cells (HepG2). The structure of the amidoxime compound is as shown in the specification. In the formula, n is 1-6, and R refers to alkyl or substituted alkyl.

Description

technical field [0001] The invention relates to a class of amidoxime compounds, a preparation method and application thereof. Background technique [0002] Histone-specific deacetylase 1 (lysine-specific demethylase1, LSD1) is the first discovered histone demethylase, which demethylates specific methylated histones and reverses histone methylation Kylation modification. The demethylation modification effect of LSD1 is not limited to the specific lysine of histone, it has the same specific demethylation modification effect on some non-histone lysine, thereby regulating its function and state. Among them, transcription factors E2F1 and p53 are the most representative. [0003] Histone methylation is a form of histone post-translational modification, which occurs on the lysine and arginine in the tail and globule of histone. Lysine can have three modification states: monomethylation (me1), dimethylation (me2) and trimethylation (me3). Lysine methylation can activate or inhib...

Claims

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Application Information

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IPC IPC(8): C07D239/95A61P35/00
CPCC07D239/95
Inventor 袁其朋邓炳华程春会云帆
Owner BEIJING UNIV OF CHEM TECH
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