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Medical application of 2-[4-(benzoxazole-2-oxy)phenoxy]amide

A technology of benzoxazole and chlorobenzoxazole, which is applied in the field of compounds, can solve the anticancer activity of 2-[4-(benzoxazole-2-oxyl)phenoxy]amide. There is no research and development report, etc. question

Inactive Publication Date: 2015-06-17
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The anticancer activity of 2-[4-(benzoxazole-2-oxyl)phenoxy]amide has not been reported

Method used

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  • Medical application of 2-[4-(benzoxazole-2-oxy)phenoxy]amide
  • Medical application of 2-[4-(benzoxazole-2-oxy)phenoxy]amide
  • Medical application of 2-[4-(benzoxazole-2-oxy)phenoxy]amide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of (R)-N-(2-chlorothiazole-5-methyl)-2-(4-(6-chloro-benzoxazole-2-oxyl)phenoxy)propionamide

[0019]

[0020] (1) Preparation of (R)-2-(4-(6-chloro-benzoxazole-2-oxyl)phenoxy)propionic acid

[0021]

[0022] Sodium hydroxide solution (20 mL, 10%), (R)-2-(4-hydroxyphenoxy)propionic acid (3.64 g, 0.02 mol) was added in batches under ice-cooling, stirred for 0.5 h, and the sodium salt solution Add dropwise to 30 mL of a toluene solution containing 2,6-dichlorobenzoxazole (3.76 g, 0.02 mol), add 0.2 g of tetrabutylammonium bromide after the dropwise addition, raise the temperature to 50°C for 3 hours, and then The temperature was raised to reflux for 1 hour. Cool, separate the water layer, adjust the pH to 3~4 with dilute hydrochloric acid, filter, wash with water, and dry to obtain (R)-2-(4-(6-chloro-benzoxazole-2-oxyl)phenoxy as a gray solid ) propionic acid 6.02 g, yield 90%.

[0023] (2) Preparation of (R)-N-(2-chlorothiazole-5-methyl)-2-(4-(6-chlor...

Embodiment 2

[0027] Antitumor Activity of 2-[4-(Benzoxazole-2-oxyl)phenoxy]amide

[0028] 1. Principle of antitumor activity

[0029] MTT bioactivity test, also known as MTT colorimetry, is a method for detecting cell survival and growth. MTT analysis uses living cell metabolite reducing agent thiazolyl blue [3-(4,5-dimethyl-2-thiazole)-2,5-diphenyltetrazolium bromide; 3-(4,5-dimethylthiazol -2-yl)-2,5-diphenyltetrazolium bromide, MTT] as the basis. MTT is a dye that accepts hydrogen atoms. The NADP-related dehydrogenase in the mitochondria of living cells can convert yellow MTT into insoluble blue-purple formazon (formazon), while dead cells have no such function. After dissolving formazon with DMSO, measure the optical density value with a microplate reader at a certain wavelength, which can quantitatively measure the survival rate of cells. The inhibitory effect of the sample on the tumor cells was observed according to the change of the optical density value.

[0030] 2. Antitumor...

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Abstract

The invention relates to 2-[4-(benzoxazole-2-oxy)phenoxy]amide represented as a chemical structural formula I and an isomer or a raceme thereof. In the formula, R<1> and R<2> are selected from H, C1-C2 alkyls and C3-C4 straight chain or branched chain alkyls, X is selected from fluorine, chlorine, bromine and iodine, X<1>, X<2>, X<3>, X<4> and X<6> are selected from hydrogen and C1-C2 alkyls, and X<5> is selected from fluorine, chlorine, bromine or iodine. The 2-[4-(benzoxazole-2-oxy)phenoxy]amide and the isomer or the raceme are applied in preparation of anticancer 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]amide 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], in which XK469 (2-(4-(7-chloroquinoxaline-2-oxyl)phenoxy)propionic acid) is a phase I clinical study conducted by DuPont Company of the United States XK469 is a new type of anti-tumor drug, which has a wide anti-tum...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12A61K31/427A61P35/00
Inventor 胡艾希丁娜刘祈星柳爱平
Owner HUNAN UNIV