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Medicinal uses of 2‑[4‑(quinoxaline‑2‑oxy)phenoxy] fatty acid pyridinamines

A fatty acyl pyridylamine and quinoxaline technology, which can be used in drug combinations, anti-tumor drugs, organic chemistry, etc., can solve the problem of no research and development reports on the anti-cancer activity of fatty acyl pyridyl amines

Inactive Publication Date: 2017-12-29
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] There is no research and development report on the anticancer activity of 2-[4-(quinoxaline-2-oxyl)phenoxy]fatty acid pyridinamine

Method used

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  • Medicinal uses of 2‑[4‑(quinoxaline‑2‑oxy)phenoxy] fatty acid pyridinamines
  • Medicinal uses of 2‑[4‑(quinoxaline‑2‑oxy)phenoxy] fatty acid pyridinamines
  • Medicinal uses of 2‑[4‑(quinoxaline‑2‑oxy)phenoxy] fatty acid pyridinamines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0019] 2-[4-(6-Chloroquinoxaline-2-oxyl)phenoxy]propionyl chloride (3.3mmol), dichloromethane (40mL), 2-amino-3-nitropyridine (3.3mmol) and catalytic Amount of 4-dimethylaminopyridine (DMAP), stirred for 10min, triethylamine (1.0g, 10mmol) was added dropwise, refluxed for 6h, the reaction solution was poured into 150ml of ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate, Precipitation, column chromatography obtains column chromatography and obtains N-(3-nitropyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propanamide, melting point 179.0~179.5℃; 1 H NMR (300MHz, CDCl 3 )δ: 1.76 (d, J=6.9Hz, 3H, CH 3 ), 4.93 (q, J=6.9Hz, 1H, CH), 7.15 (d, J=9.0Hz, 2H, benzene ring-H), 7.24 (d, J=9.0Hz, 2H, benzene ring-H), 7.29 (m, 1H, pyridine ring-H), 7.61 (dd, J 1 =9.0Hz,J 2 =2.4Hz, 1H, quinoxaline-H), 7.67(d, J=9.3, 9.0Hz, 1H, quinoxaline ring-H), ...

Embodiment 2

[0021] Preparation of N-(3-nitro-6-chloropyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propionamide

[0022] 2-[4-(6-Chloroquinoxaline-2-oxyl)phenoxy]propionyl chloride (3.3mmol), dichloromethane (40mL), 2-amino-3-nitro-6-chloropyridine and catalytic Amount of 4-dimethylaminopyridine (DMAP), stirred for 10min, triethylamine (1.0g, 10mmol) was added dropwise, refluxed for 8h, the reaction solution was poured into 150ml of ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate, Precipitation, column chromatography obtains N-(3-nitro-6-chloropyridin-2-yl)-2-[4-(6-chloroquinoxaline-2-oxyl)phenoxy]propanamide, melting point 150.3~151.6℃; 1 H NMR (300MHz, CDCl 3 )δ: 1.73 (d, J=6.9Hz, 3H, CH 3 ), 4.91 (q, J=6.9Hz, 1H, CH), 7.13 (d, J=9.3Hz, 2H, benzene ring-H), 7.24~7.28 (m, 3H, benzene ring-H, pyridine ring-H ), 7.61 (dd, J 1 =8.7Hz,J 2 =2.7Hz, 1H, quinoxaline ring-H), 7.67(d, J=8.7Hz, 1H, quinoxaline ring-H), 8.06(d, J=2.7Hz, 1H, quinoxaline r...

Embodiment 3

[0024] Preparation of N-(pyridin-2-yl)-2-[4-(quinoxaline-2-oxyl)phenoxy]fatty acid amide (Ⅰ)

[0025]

[0026] where R, R 1 Selected from: Hydrogen, Deuterium, C 1 ~C 2 Alkyl, C 3 ~C 4 Straight chain or branched chain alkyl; X 1 、X 2 、X 4 、X 5 、X 7 、X 9 、X 10 Selected from: Hydrogen, Deuterium, C 1 ~C 2 Alkyl; X 3 From: Nitro; X 6 Selected from: Hydrogen, Deuterium, C 1 ~C 2 Alkyl, fluorine, chlorine, bromine; X 8 is selected from: fluorine, chlorine, bromine.

[0027] N-(pyridin-2-yl)-2-[4-(quinoxaline-2-oxyl)phenoxy]fatty acid amide was prepared according to the method of Example 1.

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Abstract

The invention relates to 2-[4-(quinoxaline-2-oxyl)phenoxyl]fatty acyl pyridylamine as shown in the chemical structural formula II or formula II. In the formula, R and R<1> are selected from hydrogen, deuterium, C1-C2 alkyl group, C3-C4 straight chain or branched alkyl group; X<1>, X<2>, X<4>, X<5>, X<7>, X<9> and X<10> are selected from hydrogen, deuterium and C1-C2 alkyl group; X<3> is selected from nitro group; X<6> is selected from hydrogen, deuterium, C1-C2 alkyl group, fluorine, chlorine and bromine; and X<8> is selected from fluorine, chlorine and bromine. The 2-[4-(quinoxaline-2-oxyl)phenoxyl]fatty acyl pyridylamine is applied in preparation of anti-cancer drugs.

Description

technical field [0001] The present invention relates to a class of compounds and new applications thereof, in particular to the application of 2-[4-(quinoxaline-2-oxyl)phenoxy] fatty acid pyridinamine in the preparation of anticancer drugs. Background technique [0002] 4-Aryloxyphenoxyalkanoic acid derivatives have a wide range of biological activities, among which aryloxyphenoxypropionic acid derivatives are their typical representatives, and there are more than 20 commercial varieties in agricultural herbicides. At the same time, 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 trial conducted by DuPont Company of the United States. A new type of anti-tumor drug studied, XK469 has ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61K31/498A61P35/00
CPCC07D401/12
Inventor 胡艾希杨斌刘祈星叶姣王宇毛春晖
Owner HUNAN UNIV
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