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4-oxethyl-2-hydroxyl-6-methyl benzoic acid as well as medicinal composition and application thereof

A technology of methyl benzoic acid and ethoxy, which is applied in the field of chemical medicine, can solve the problems of high toxicity and side effects of drugs, drug resistance of cancer cells, and uncertain curative effect, so as to inhibit the proliferation of cancer cells and regulate the cycle and differentiation of cancer cells , the effect of promoting apoptosis of cancer cells

Inactive Publication Date: 2014-01-01
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Many cancer chemotherapy drugs currently used in clinical practice have problems such as large toxic and side effects, uncertain curative effect, poor selectivity, and drug resistance of cancer cells, which greatly restricts the clinical application and effect of cancer chemotherapy.

Method used

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  • 4-oxethyl-2-hydroxyl-6-methyl benzoic acid as well as medicinal composition and application thereof
  • 4-oxethyl-2-hydroxyl-6-methyl benzoic acid as well as medicinal composition and application thereof
  • 4-oxethyl-2-hydroxyl-6-methyl benzoic acid as well as medicinal composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis and structural identification of the compound 4-ethoxy-2-hydroxy-6-methylbenzoic acid (4-ethoxy-2-hydroxy-6-methylbenzoic acid) represented by formula (1)

[0049] 1. Preparation method

[0050] Phase Transfer Catalytic Synthesis and Column Chromatographic Separation

[0051] Using phase transfer catalysis, in the presence of sodium hydroxide, 2,4-dihydroxy-6-methylbenzoic acid and diethyl sulfate (molar ratio is 0.2:0.18), in the catalyst HA-1 (dioctadecane Base methylamine benzyl quaternary ammonium chloride) under the action of 60-65 ℃ for 3h. After the reaction is completed, cool to 25°C, pour into ice water, adjust the pH value to neutral with dilute hydrochloric acid, separate the organic layer; extract the water layer with toluene twice, combine the organic layer; wash the organic layer three times with anhydrous sulfuric acid Sodium dry. The solvent toluene was distilled off under reduced pressure, and the product was separated and purifi...

Embodiment 2

[0056] Embodiment 2: The biological experiment result of formula (1) compound 4-ethoxyl-2-hydroxyl-6-methylbenzoic acid

[0057] The following are some specific experimental examples to illustrate the formula (1) compound 4-ethoxy-2-hydroxy-6-methylbenzoic acid of the present invention (indicated by D6B2 or D in the following charts, the same below; D1 is 200 μM, D2 150 μM for D3, 100 μM for D3, 50 μM for D4, and 25 μM for D5) have significant and selective anti-tumor effects, combined anti-tumor effects with clinical anti-tumor drugs, as well as their toxicological safety and anti-tumor mechanism.

[0058] 1. In vitro anticancer effect of 4-ethoxy-2-hydroxy-6-methylbenzoic acid:

[0059] Test method: The compound 4-ethoxy-2-hydroxy-6-methylbenzoic acid of formula (1) was dissolved in DMSO, and the anticancer test was carried out in vitro according to the final concentration of 25, 50, 100, 150 and 200 μM. Human or animal tumor cells in logarithmic growth phase were collected...

Embodiment 3

[0110] Formula (1) compound 4-ethoxy-2-hydroxy-6-methylbenzoic acid and sodium bicarbonate are neutralized under heating conditions, then adjust the pH value to 7.0-7.5 with soda ash solution, heat, evaporate, Crystallization forms the sodium salt of the compound of formula (1), Sodium4-ethoxy-2-hydroxy-6-methylbenzoate, which is soluble in water. The compounds of formula (1) can also form salts with other basic ions or groups.

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Abstract

The invention discloses 4-oxethyl-2-hydroxyl-6-methyl benzoic acid with a structure shown in a formula (1) as well as a medicinal composition and an application thereof. The compound is capable of significantly killing and / or inhibiting the various tumour cells of human and animals in vivo and in vitro, the compound has a significant combined antitumour effect with clinic antitumour medicines, and the compound or the pharmaceutically acceptable salts thereof can be applied to preparation of antitumour medicines, antitumour medicine compositions, combined antitumour medicine compositions or auxiliary antitumour healthcare products. The compound is capable of significantly promoting the apoptosis and necrosis of cancer cells, adjusting the growth cycle of cancer cells, and inhibiting the proliferation of cancer cells. The compound has no significant toxicity on the ponderal growth and organ development of mice under an effective anticancer dosage, or the toxic effect significance of the compound is lower than clinic anticancer medicines such as cyclophosphamide and 5-fluorouracil.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and in particular relates to 4-ethoxy-2-hydroxy-6-methylbenzoic acid and its medicinal composition and application. Background technique [0002] Cancer is a major disease that seriously threatens human health and life safety, and has become the number one cause of death for human beings. According to the global cancer statistics report, in 2008, there were 12.661 million new cancer cases and 7.564 million deaths in the world; 2.816 million new cancer cases and 1.958 million deaths in China. "2012 China Tumor Registration Annual Report" revealed that there were 3.12 million new cancer cases in China in 2012, and an average of 6 people were diagnosed with malignant tumors every minute. The incidence of cancer is still rising, and cancer has become a major health problem that seriously threatens people's health and life safety. [0003] Cancer is still an incurable disease in the world. Che...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/21C07C51/347A61K33/24A61K31/675A61K31/60A61P35/00A23L1/29A61K31/513A61K31/337A23L33/00
CPCC07C51/367C07C65/21A61K31/11A61K31/192A61K31/235A61K45/06A61P35/00C07C37/01C07C39/08C07C45/29C07C47/565A61K2300/00
Inventor 贺小琼詹华强黄清龙
Owner THE HONG KONG UNIV OF SCI & TECH
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