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2-phenoxy quinoxaline derivative and pharmaceutical use thereof

A technology of phenoxyquinoxaline and derivatives, applied in the field of compounds, can solve the problem that the inhibitory activity of 2-phenoxyquinoxaline derivatives is not reported, and achieve the effects of easy industrial production and simple preparation method

Active Publication Date: 2015-08-05
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 2-Phenoxyquinoxaline Derivatives Have No Report on Toxic Neuraminidase Inhibitory Activity

Method used

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  • 2-phenoxy quinoxaline derivative and pharmaceutical use thereof
  • 2-phenoxy quinoxaline derivative and pharmaceutical use thereof
  • 2-phenoxy quinoxaline derivative and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of (R)-N-(3-chloropyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propionamide

[0019]

[0020] (R)-2-[4-(6-Chloroquinoxaline-2-oxyl)phenoxy]propionyl chloride 3.3mmol, dichloromethane 40mL, 2-amino-3-chloropyridine 3.3mmol and catalytic amount of 4 -Dimethylaminopyridine (DMAP), stirred for 10min, dripped into triethylamine 10mmol, refluxed for 5h, the reaction solution was poured into 150ml of ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate, precipitated, and obtained by column chromatography ( R)-N-(3-chloropyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propanamide, yield 69.1%, m.p.168.3~173.4℃ ; 1 H NMR (300MHz, CDCl 3 )δ: 1.75 (d, J=6.6Hz, 3H, CH 3 ), 4.93 (q, J=6.6Hz, 1H, CH), 7.07~7.13 (m, 3H, 2 benzene ring-H, pyridine ring-H), 7.26 (d, J=9.3Hz, 2H, benzene ring- H), 7.58~7.76 (m, 3H, quinoxaline ring-H, pyridine ring-H), 8.05 (d, J=2.1Hz, 1H, quinoxaline ring-H), 8.46 (dd, J 1 = 4.8Hz,J 2 =1...

Embodiment 2

[0022] Preparation of N-(5-nitropyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propionamide

[0023]

[0024] 2-[4-(6-Chloroquinoxaline-2-oxyl)phenoxy]propionyl chloride 3.3mmol, dichloromethane 40mL, 2-amino-5-nitropyridine 3.3mmol and catalytic amount of 4-dimethyl Aminopyridine (DMAP), stirred for 10min, dripped into triethylamine 10mmol, refluxed for 7h, the reaction solution was poured into 150ml of ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate, precipitated, and obtained N-(5 -Nitropyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propionamide, yield 39.8%, m.p.165.8~166.5°C; 1 H NMR (300MHz, CDCl 3 )δ: 1.72 (d, J=6.6Hz, 3H, CH 3 ), 4.90 (q, J=6.6Hz, 1H, CH), 7.07 (d, J=9.0Hz, 2H, benzene ring-H), 7.28 (d, J=9.0Hz, 2H, benzene ring-H), 7.59 (dd, J 1 =9.0,J 2 =2.4Hz, 1H, quinoxaline ring-H), 7.66 (d, J=9.0, 1H, quinoxaline ring-H), 8.05 (d, J=2.4Hz, 1H, quinoxaline ring-H) , 8.50 (dd, J=9.3, 0.9Hz, 1H, pyridine ring-H...

Embodiment 3

[0026] Preparation of N-(3-nitro-6-methoxypyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propionamide

[0027]

[0028] 2-[4-(6-Chloroquinoxaline-2-oxyl)phenoxy]propionyl chloride 3.3mmol, dichloromethane 40mL, 2-amino-6-methoxyl-3-nitropyridine 3.3mmol and catalyst The amount of 4-dimethylaminopyridine (DMAP), stirred for 10min, dripped into 10mmol of triethylamine, refluxed for 7h, the reaction solution was poured into 150ml of ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate, precipitated, and column layer Analyze and obtain N-(3-nitro-6-methoxypyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propanamide yield 36.6%, m.p.156.8~157.7℃; 1 H NMR (300MHz, CDCl 3 )δ: 1.75 (d, J=6.6Hz, 3H, CH 3 ), 4.13 (s, 3H, OCH 3 ), 4.90 (q, J=6.6Hz, 1H, CH), 6.58 (d, J=9.0Hz, 1H, pyridine ring-H), 7.16 (d, J=9.0Hz, 2H, benzene ring-H), 7.23 (d, J=9.0Hz, 2H, benzene ring-H), 7.62 (dd, J 1 =9.0Hz,J 2 =2.4Hz, 1H, quinoxaline ring-H), 7.67 (...

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Abstract

The invention discloses a 2-phenoxy quinoxaline derivative and pharmaceutical use thereof. The chemical structural formula of the 2-phenoxy quinoxaline derivative is shown as formula I or II in the specification, wherein R1 and R2 are selected from hydrogen and C1-C2 alkyl; X1 is selected from fluorine, chlorine, bromine or iodine; X2 is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, bromine, iodine or nitro; X3 is selected from hydrogen, C1-C2 alkyl or nitro; and X4 is selected from hydrogen, C1-C2 alkyl, methoxy, cyano or amino. The invention also relates to a pharmaceutical composition containing the compound and application of the 2-phenoxy quinoxaline derivative in preparation of anti-influenza virus neuraminidase inhibitors.

Description

technical field [0001] The invention relates to a compound, in particular to a 2-phenoxyquinoxaline derivative and its medical use. Background technique [0002] 4-Aryloxyphenoxyalkanoic acid derivatives have also been widely reported in the research of anticancer drugs [Investigational New Drugs, 1999, 16:287–296; Investigational New Drugs, 1998, 16:129–139; Acta Pharmaceutica Sinica, 2005, 40(9):814-819], wherein XK469 (2-(4-(7-chloroquinoxalin-2-yloxy)phenoxy)propionic acid) is a phase I clinical study conducted by DuPont Company of the United States A new type of antitumor drug, XK469 has a wide antitumor spectrum, few side effects, and is effective for a variety of solid tumor models, such as colon cancer Colon38 and breast cancer [J Med Chem, 2001, 44 (11): 1758-76 ]. The Chinese invention patents for the application of 2-phenoxyalkanamide are as follows: (1) 2-[4-(Benzoxazol-2-yloxy)phenoxy]alkanamide and its application, CN103086995A, published on May 8, 2013 ; (2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61K31/498A61P31/16
CPCC07D401/12
Inventor 刘祈星胡艾希
Owner CHINA THREE GORGES UNIV
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