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The medical use of 2-(4-phenoxyphenoxy) fatty acid pyridinamine

A technology of phenoxyphenoxy and fatty acylpyridinamine, which is applied in the application field of 2-fatty acylpyridinylamine in the preparation of anticancer drugs, and can solve the problem of 2-(4-phenoxyphenoxy) fatty acyl There are no research and development reports on the anticancer activity of pyridinamine

Inactive Publication Date: 2017-10-31
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • The medical use of 2-(4-phenoxyphenoxy) fatty acid pyridinamine
  • The medical use of 2-(4-phenoxyphenoxy) fatty acid pyridinamine
  • The medical use of 2-(4-phenoxyphenoxy) fatty acid pyridinamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of N-(3-nitropyridin-2-yl)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0021] 2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionyl chloride (3.3mmol), dichloromethane (40mL), 2-amino-3-nitropyridine (3.3mmol) and Catalytic amount of 4-dimethylaminopyridine (DMAP), stir for 10min, add triethylamine (1.0g, 10mmol) dropwise, reflux for 7h, pour the reaction solution into 150ml ice water, extract with dichloromethane, and dry with anhydrous sodium sulfate , Desolvation, column chromatography to obtain N-(3-nitropyridin-2-yl)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide, yellow viscous body; 1 HNMR(300MHz, CDCl 3 )δ: 1.74 (d, J = 6.6 Hz, 3H, CH 3 ), 4.90 (q, J = 6.6 Hz, 1H, CH), 6.89 (t, J = 8.4 Hz, 1H, C 6 H 3 ), 7.04~7.11(m, 4H, C 6 H 4 ), 7.27~7.37(m, 2H, C 6 H 3 ), 7.45(dd, J 1 =10.2Hz, J 2 =1.8Hz, 1H, pyridine ring-H), 8.53 (dd, J 1 =8.4Hz, J 2 = 1.8 Hz, 1H, pyridine ring-H), 8.78~8.80 (m, 1H, pyridine ring-H), 11.14 (s, 1H, NH); LC-MS, m / z: 423.0 [M+...

Embodiment 2

[0023] Preparation of N-(6-amino-5-nitropyridin-2-yl)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0024] 2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionyl chloride (3.3mmol), dichloromethane (40mL), 2,6-diamino-3-nitropyridine (3.3 mmol) and catalytic amount of 4-dimethylaminopyridine (DMAP), stir for 10 min, add triethylamine (1.0 g, 10 mmol) dropwise, reflux for 10 h, pour the reaction solution into 150 ml ice water, extract with dichloromethane, anhydrous Dry over sodium sulfate, remove the solvent, and obtain N-(6-amino-5-nitropyridin-2-yl)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy by column chromatography ] Propionamide, melting point 114.4~116℃; 1 H NMR(300MHz, CDCl 3 )δ: 1.67 (d, J = 6.9 Hz, 3H, CH 3 ), 4.80 (q, J = 6.9 Hz, 1H, CH), 6.89-7.08 (m, 5H, benzene ring-H), 7.34-7.38 (m, 1H, C 6 H 3 ), 7.46(dd, J 1 =9.9Hz, J 2 = 1.8 Hz, 1H, benzene ring-H), 7.73 (d, J=9.3 Hz, 1H, pyridine ring-H), 8.47 (d, J=9.3 Hz, 1H, pyridine ring-H), 8.89 (br. s, 1H, NH); LC-MS, m / z: 438....

Embodiment 3

[0026] Preparation of N-(pyridin-2-yl)-2-(4-phenoxyphenoxy) fatty amide (I)

[0027]

[0028] Where R, R 1 Selected from: hydrogen, deuterium, C 1 ~C 2 Alkyl, C 3 ~C 4 Straight or branched chain alkyl; X 1 , X 2 , X 4 , X 6 , X 7 , X 9 Selected from: hydrogen, deuterium or C 1 ~C 2 Alkyl; X 3 Selected from: fluorine, chlorine, bromine; X 5 Selected from: cyano; X 8 , X 10 Selected from: hydrogen, deuterium, C 1 ~C 2 Alkyl or nitro; X 11 Selected from: hydrogen, deuterium, C 1 ~C 2 Alkyl or amino.

[0029] The N-(pyridin-2-yl)-2-(4-phenoxyphenoxy) fatty amide (I) was prepared according to the method of Example 1.

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Abstract

The invention relates to 2-(4-phenoxyphenoxy)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 branched alkyl group; X<1>, X<2>, X<4>, X<6>, X<7> and X<9> are selected from hydrogen, deuterium or C1-C2 alkyl group; X<3> is selected from fluorine, chlorine and bromine; X<5> is selected from cyanogroup; X<8> and X<10> are selected from hydrogen, deuterium, C1-C2 alkyl group or nitro group; and X<11> is selected from hydrogen, deuterium, C1-C2 alkyl group or amino group. The 2-(4-phenoxyphenoxy)fatty acyl pyridylamine is applied in preparation of anti-cancer drugs.

Description

Technical field [0001] The invention relates to a class of compounds and new uses thereof, in particular to the use of 2-(4-phenoxyphenoxy) fatty acid pyridylamine 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 typical representatives, and there are more than 20 commercialized 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], where XK469 (2-(4-(7-chloroquinoxalin-2-yloxy)phenoxy)propionic acid) is currently undergoing phase I clinical trials by DuPont A new type of anti-tumor drug studied, XK469 has a broad anti-tumor spectrum, small side effects, and is effective ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/75A61K31/4409A61K31/44A61K31/4402A61P35/00A61P11/00
CPCC07D213/75
Inventor 胡艾希方毅林刘祈星丁娜
Owner HUNAN UNIV