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Medical use of 2-[4-(benzoxazole-2-oxyl)phenoxy] fatty acid pyridinamine

A technology of fatty acylpyridinamine and benzoxazole, which can be applied in the fields of drug combination, antineoplastic drugs, organic chemistry, etc., and can solve the problem that there is no research and development report on the anticancer activity of fatty acylpyridinamine

Inactive Publication Date: 2018-01-19
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The anticancer activity of 2-[4-(benzoxazole-2-oxyl)phenoxy]fatty acid pyridinamine has no research and development report

Method used

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  • Medical use of 2-[4-(benzoxazole-2-oxyl)phenoxy] fatty acid pyridinamine
  • Medical use of 2-[4-(benzoxazole-2-oxyl)phenoxy] fatty acid pyridinamine
  • Medical use of 2-[4-(benzoxazole-2-oxyl)phenoxy] fatty acid pyridinamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of N-(3-nitropyridin-2-yl)-2-[4-(6-chlorobenzoxazol-2-oxyl)phenoxy]propionamide

[0020] 2-[4-(6-Chlorobenzoxazole-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, added dropwise triethylamine (1.0g, 10mmol), refluxed for 7h, the reaction solution was poured into 150ml ice water, dichloromethane extracted, anhydrous sodium sulfate Drying, precipitating, column chromatography obtains N-(3-nitropyridin-2-yl)-2-[4-(6-chlorobenzoxazole-2-oxyl)phenoxy]propionamide, melting point 156.0~156.3℃; 1 H NMR (300MHz, CDCl 3 )δ: 1.74 (d, J=6.6Hz, 3H, CH 3 ), 4.90(q, J=6.6Hz, 1H, CH), 7.12~7.45(m, 8H, benzene ring-H, pyridine ring-H, benzoxazole-H), 8.53(dd, J 1 =8.1Hz,J 2 =1.2Hz, 1H, pyridine ring-H), 8.79(d, J=3.0Hz, 1H, benzoxazole-H), 11.20(s, 1H, NH); 13 C NMR (75MHz, CDCl 3 )δ: 18.45, 75.70, 110.64, 116.59, 119.19, 119.76, 121.63, 12...

Embodiment 2

[0022] Preparation of N-(pyridin-2-yl)-2-[4-(benzoxazole-2-oxyl)phenoxy]fatty acid amide (I)

[0023]

[0024] 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 6 、X 7 、X 8 、X 10 selected from: hydrogen, deuterium or C 1 ~C 2 Alkyl; X 3 is selected from: fluorine, chlorine, bromine; X 3 From: Nitro; X 9 is selected from: fluorine, chlorine, bromine.

[0025] N-(pyridin-2-yl)-2-[4-(benzoxazole-2-oxyl)phenoxy]fatty acid amide (I) was prepared according to the method in Example 1.

Embodiment 3

[0027] Preparation of N-(pyridin-2-yl)-2-[4-(benzoxazole-2-oxyl)phenoxy]fatty acid amide (Ⅱ)

[0028]

[0029] 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 6 、X 7 、X 8 、X 10 selected from: hydrogen, deuterium or C 1 ~C 2 Alkyl; X 3 is selected from: fluorine, chlorine, bromine; X 3 From: Nitro; X 9 is selected from: fluorine, chlorine, bromine.

[0030]N-(pyridin-2-yl)-2-[4-(benzoxazol-2-oxyl)phenoxy]fatty acid amide (II) was prepared according to the method in Example 1.

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Abstract

The invention relates to 2-[4-(benzoxazole-2-oxyl)phenoxyl]fatty acyl pyridylamine as shown in the chemical structural formula I or formula II. In the formula, R and R<1> are selected from hydrogen, deuterium, C1-C2 alkyl group, C3-C4 straight chain or brachned alkyl group; X<1>, X<2>, X<4>, X<5>, X<6>, X<7>, X<8> and X<10> are selected from hydrogen, deuterium or C1-C2 alkyl group; X<3> is selected from fluorine, chlorine and bromine; X<3> is selected from nitro group; and X<9> is selected from fluorine, chlorine and bromine. The 2-[4-(benzoxazole-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-(benzoxazole-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): C07D413/12A61K31/4439A61P35/00
CPCC07D413/12
Inventor 胡艾希赵东江刘祈星颜晓维王宇毛春晖
Owner HUNAN UNIV
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