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2-(4-aryloxyphenoxy)alkylamide and application thereof

A technology of aryloxyphenoxy and alkamide, applied in the direction of nitrile/isonitrile active ingredients, organic chemistry, drug combination, etc., can solve the problem of 2-(4-aryloxyphenoxy)alkanamide or its optical There are no research and development reports on the anticancer activity of isomers

Inactive Publication Date: 2013-05-08
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-aryloxyphenoxy)alkanamides or their optical isomers

Method used

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  • 2-(4-aryloxyphenoxy)alkylamide and application thereof
  • 2-(4-aryloxyphenoxy)alkylamide and application thereof
  • 2-(4-aryloxyphenoxy)alkylamide and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of (R)-N-propargyloxy-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0019]

[0020] (1) Preparation of (R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionic acid

[0021] N,N-Dimethylformamide (DMF, 40 mL), (R)-2-(4-hydroxyphenoxy)propionic acid (3.64 g, 0.02 mol), and potassium carbonate (5.41 g 0.04 mol) were added in portions , stirred at 70-80 °C for 1 h, added a DMF solution of 3,4-difluorobenzonitrile (2.78 g, 0.02 mol) dropwise, and continued stirring for 5-6 h. Cool to room temperature, pour into ice water (250 mL), slowly add dilute hydrochloric acid, adjust to pH 4~5, filter, wash with water, and dry to obtain 5.20 g of the title compound as a gray solid, with a yield of 86.4%.

[0022] (2) Preparation of (R)-N-propargyloxy-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0023] Toluene (40 mL), (R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid (1.01 g, 3.3 mmol) and thionyl chloride (1.18 g, 10 mmol). Reflux for 5 h, remove ...

Embodiment 2

[0025] Preparation of (R)-N-(3,3-dichloro-2-allyloxy)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0026]

[0027] (R)-N-(3,3-dichloro-2-allyloxy)-2-[4-(4-cyano-2-fluorophenoxy) of white solid was obtained according to the method of Example 1 Phenoxy]propionamide. Melting point 92.2~92.7 ℃, 1 H NMR (300 MHz, CDCl 3 ) δ: 1.62 (d, J=6.6 Hz, 3H, CHC H 3 ), 4.55 (d, J=6.9 Hz, 2H, OCH 2 ), 4.73 (q, J=6.6 Hz, 1H, C H CH 3 ), 6.14 (t, J=7.2 Hz, 1H, =CH), 6.87~7.49 (m, 7H, C 6 h 4 , C 6 h 3 ), 8.93 (s, 1H, NH); LC-MS (Pos M + ) m / z): 425.

Embodiment 3

[0029] Preparation of (R,Z)-N-(3-chloroallyloxy)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0030]

[0031](R, Z)-N-(3-chloro-allyloxy)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy was obtained as a white solid by the method of Example 1 ] Propionamide. Melting point 95.2~96.3 ℃, 1 H NMR (300 MHz, CDCl 3 ) δ: 1.61 (d, J=6.6 Hz, 3H, CHC H 3 ), 4.67 (d, J=6.6 Hz, 2H, OCH 2 ), 4.74 (q, J=6.9 Hz, 1H, C H CH 3 ), 6.02~6.08 (m, 1H, OCH 2 C H ), 6.30 (d, J=7.5 Hz, 1H, =CHCl), 6.87~7.49 (m, 7H, C 6 h 4 , C 6 h 3 ), 8.93 (s, 1H, NH); LC-MS (Pos M + ) m / z): 391.

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PUM

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Abstract

The invention relates to 2-(4-aryloxyphenoxy)alkylamide represented by a chemical structural formula I or an optical isomer thereof, wherein R1 is selected from H, C1-C1 alkyl, and C3-C4 straight-chain or branched-chain alkyl; R2 is selected from allyl, propargyl, halogenated allyl, and halogenated propargyl; X1-X6 are selected from hydrogen, C1-C2 alkyl, fluoro, chloro, bromo, or cyan. The invention also relates to the application of the 2-(4-aryloxyphenoxy)alkylamide or the optical isomer thereof in preparing anti-lung-adenocarcinoma medicines.

Description

technical field [0001] The present invention relates to a class of novel compounds and their uses, specifically 2-(4-aryloxyphenoxy)alkanamides or their optical isomers and their use in the preparation of anticancer drugs. Background technique [0002] 4-Aryloxyphenoxyalkanoic acid derivatives have a wide range of biological activities, and aryloxyphenoxypropionic acid derivatives are their typical representatives, and there are more than 20 commercial varieties in agricultural herbicides [DE2640730, DE3004770 , US4713109, EP302203, JP54022371, EP4414, US: 20030096706], the main mode of action is to inhibit plant acetyl-CoA carboxylase, thereby affecting the synthesis of plant fatty acids and causing plant death to achieve the purpose of weeding. 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 Pharmac...

Claims

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Application Information

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IPC IPC(8): C07C259/06A61K31/277A61P35/00
Inventor 胡艾希刘祈星柳爱平李婉颜晓维方毅林
Owner HUNAN UNIV
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