2-[4-(quinoxaline-2-oxygroup) phenoxy] alkylamide and application thereof

A quinoxaline and oxy-based technology, applied in the field of new compounds, can solve the problem of no research and development reports on anti-cancer activity

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-(quinoxalin-2-yloxy)phenoxy]alkanamide or its optical isomers

Method used

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  • 2-[4-(quinoxaline-2-oxygroup) phenoxy] alkylamide and application thereof
  • 2-[4-(quinoxaline-2-oxygroup) phenoxy] alkylamide and application thereof
  • 2-[4-(quinoxaline-2-oxygroup) phenoxy] alkylamide and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of (R)-N-(propargyloxy)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionamide

[0019]

[0020] (1) Preparation of (R)-2-(4-(6-chloroquinoxalin-2-yloxy)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 2,6-dichloroquinoxaline (3.98 g, 0.02 mol), and stirred at 130-140 °C for 5~6 h. Cool to room temperature, pour into ice water (250 mL), slowly add dilute hydrochloric acid, adjust the pH to 4~5, filter, wash with water, and dry to obtain 6.60 g of the title compound with a yield of 95.9%.

[0022] (2) Preparation of (R)-N-(propargyloxy)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionamide

[0023] Toluene (40 mL), (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoic acid (1.15 g, 3.3 mmol) and thionyl chloride (1.18 g, 10 mmol), refluxed for 4 h to remove the solvent toluene...

Embodiment 2

[0025] Preparation of (R)-N-(3,3-dichloro-2-allyloxy)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionamide

[0026]

[0027](R)-N-(3,3-dichloro-2-allyloxy)-2-[4-(6-chloroquinoxalin-2-yloxy) of white solid was obtained according to the method of Example 1 Phenoxy]propionamide. Melting point 134.8~135.6 ℃, 1 H NMR (300 MHz, CDCl 3 ) δ: 1.64 (d, J = 6.9 Hz, 3H, CHC H 3 ), 4.59 (d, J = 6.9 Hz, 2H, OCH 2 ), 4.80 (q, J = 6.9 Hz, 1H, C H CH 3 ), 6.15 (t, J = 6.9 Hz, 1H, OCH 2 C H ), 6.97 (d, J = 9.0 Hz, 2H, C 6 h 4 ), 7.24 (d, J = 9.0 Hz, 2H, C 6 h 4 ), 7.59 (dd, J 1 = 8.7 Hz, J 2 = 2.4 Hz, 1H, quinoxalin-H), 7.62 (d, J = 8.7 Hz, 1H, quinoxalin-H), 8.06 (d, J = 2.4 Hz, 1H, quinoxalin-H), 8.69 (s, 1H, quinoxalin -H), 9.05 (brs, 1H, NH). 13 C NMR (75 MHz, CDCl 3 ) δ: 18.76, 72.54, 75.35, 116.39, 122.82, 123.63, 127.00, 127.88, 128.69, 131.19, 132.92, 138.38, 139.68, 140.02, 147,00, 153.98, 157.02, 169.6 + ) m / z): 468.

Embodiment 3

[0029] Preparation of (R,Z)-N-(3-chloroallyloxy)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionamide

[0030]

[0031] According to Example 1, (R, Z)-N-(3-chloroallyloxy)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propane was obtained as a white solid amides. Melting point 132.2~133.4 ℃, 1 H NMR (300 MHz, CDCl 3 ) δ: 1.64 (d, J = 6.9 Hz, 3H, CHC H 3 ), 4.67 (dd, J 1 = 6.6 Hz, J 2 = 1.2 Hz, 2H, OCH 2 ), 4.79 (q, J = 6.9 Hz, 1H, C H CH 3 ), 6.02~6.09 (m, 1H, OCH 2 C H ), 6.33 (d, J = 7.2 Hz, 1H, =CClH), 6.98 (d, J = 9.0 Hz, 2H, C 6 h 4 ), 7.21 (d, J = 9.0 Hz, 2H, C 6 h 4 ), 7.60 (dd, J 1 = 8.7 Hz, J 2 = 2.4 Hz, 1H, quinoxalin-H), 7.69 (d, J = 8.7 Hz, 1H, quinoxalin-H), 8.07 (d, J = 2.4 Hz, 1H, quinoxalin-H), 8.69 (s, 1H, quinoxalin -H), 8.69 (brs, 1H, NH). 13 C NMR (75 MHz, CDCl 3 ) δ: 18.78, 71.27, 75.38, 116.43, 122.79, 123.70, 125.44, 127.89, 128.69, 131.22, 132.94, 138.39, 139.66, 140.02, 146.97, 154.01, 157.04, 169Pos (MLC-MS.35 + ) m / z): 434.

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Abstract

The invention relates to 2-[4-(quinoxaline-2-oxygroup) phenoxy] alkylamide shown as a chemical structural formula I or an optical isomer thereof. In the formula, R1 is selected from H, C1-C1alkyl, C3-C4 straight-chain or branch-chain alkyl; R2 is selected from allyl, propargyl, halogenated allyl, halogenated propargyl; and X1-X6 are selected from hydrogen, C1-C2 alkyl, trifluoromethyl, fluorine, chlorine, bromine, nitryl or trifluoromethoxy. The invention further discloses an application of 2-[4-(quinoxaline-2-oxygroup) phenoxy] alkylamide or the optical isomer thereof in preparation of anti-lung adenocarcinoma drugs.

Description

technical field [0001] The present invention relates to a class of novel compounds and their uses, specifically 2-[4-(quinoxalin-2-yloxy)phenoxy]alkanamides or their optical isomers and their use in the preparation of anti-lung adenocarcinoma A549 application in medicine. 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; Investi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/44A61P35/00
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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