Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Phenylacetic acid derivatives and their antitumor applications

A use, tumor technology, applied in the field of pharmacy, can solve problems such as reproductive system damage, liver and kidney function damage, etc.

Inactive Publication Date: 2016-12-28
JINGPENGHUI PHARMA
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above drugs have more or less side effects, such as cytotoxic drugs, which generally cause patients with moderate to severe digestive system reactions (such as malignant vomiting, stomatitis), bone marrow suppression (such as leukopenia, thrombocytopenia) and organ toxicity (such as Neurotoxicity, liver and kidney toxicity), hormone balance interference drugs can cause mild to moderate gastrointestinal reactions, reproductive system damage and even mental depression symptoms in patients, and most regulators and inducers can also cause patients with varying degrees of skin reactions and liver and kidney damage

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Phenylacetic acid derivatives and their antitumor applications
  • Phenylacetic acid derivatives and their antitumor applications
  • Phenylacetic acid derivatives and their antitumor applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Example 1 Synthesis of methyl 3-hydroxy-4-methoxyphenylacetate (DO-2)

[0114]

[0115] 3-Hydroxy-4-methoxy-phenylacetic acid (DO-1, 2.5g, 13.7mmol) was dissolved in 50mL of methanol, 0.2mL of concentrated sulfuric acid was added under stirring conditions, and heated to reflux for 3 hours. Cool to room temperature, concentrate the reaction solution on a rotary evaporator, dilute the obtained oil into 100 mL of ethyl acetate solution, wash the organic phase with saturated brine (50 mL*2), dry and filter with anhydrous sodium sulfate, and concentrate by rotary The solvent was removed, and the solute was purified by column chromatography (mobile phase: petroleum ether: ethyl acetate = 3:1) to obtain DO-2 (2.1g, 79%) as a colorless oil.

[0116] 1H-NMR (400MHz, CDCl 3 )δ6.80 (s, 1H), 6.75-6.68 (m, 2H), 5.56 (s, 1H), 3.81 (s, 3H), 3.62 (s, 3H), 3.31 (s, 3H).

Embodiment 2

[0117] Example 2 Synthesis of Ethoxymethyl 3,4-Dihydroxyphenylacetate (DO-3)

[0118]

[0119] 3,4-Dihydroxyphenylacetic acid (DO, 5.0g, 30.0mmol) and triethylamine (9.1g, 90.0mmol) were dissolved in 30mL of dichloromethane, and 2.84g of chloromethyl ethyl ether (30.0mmol ), and the reaction mixture was stirred overnight at room temperature. The reaction solution was mixed with 0.1N HCl solution (15mL) and NaHCO 3 solution (15mL), the organic phase was dried and filtered with anhydrous sodium sulfate, the solvent was removed by rotary concentration, and the solute was purified by column chromatography (mobile phase: petroleum ether: ethyl acetate = 2:1) to obtain a colorless oil DO- 3 (2.0g, 29.5%).

[0120] 1 H-NMR (400MHz, CDCl 3 )δ6.72(d,J=2.0Hz,1H),6.69(s,1H),6.62(m,1H),5.65(brs,1H),5.45(brs,1H),5.24(s,2H), 3.60(q,J=6.4Hz,2H),3.48(s,2H),1.14(t,J=6.4Hz,H).

Embodiment 3

[0121] Example 3 Synthesis of ethyl 3,4-dihydroxyphenylacetate (D80)

[0122]

[0123] 3,4-Dihydroxyphenylacetic acid (DO, 3.0g, 17.9mmol) was dissolved in 25mL of ethanol, and a catalytic amount of concentrated sulfuric acid was added under stirring conditions, and heated to reflux for 12 hours. Cooled to room temperature, the reaction solution was concentrated on a rotary evaporator, and the obtained oil was diluted into 50 mL of ethyl acetate solution, and the organic phase was washed with saturated NaHCO 3 solution (25mL*2) and saturated brine (25mL), dried and filtered over anhydrous sodium sulfate, then concentrated by rotation to remove the solvent, and the solute was purified by column chromatography (mobile phase: petroleum ether: ethyl acetate = 10:1) to obtain Colorless oil D80 (1.1 g, 88.5%).

[0124] 1 H-NMR(300MHz,DMSO-d6)δ8.86(s,1H),8.77(s,1H),6.66-6.63(m,2H),6.47(dd,J=8.1,2.1Hz,1H),4.08 -3.99 (m, 2H), 3.42 (s, 2H), 1.20-1.14 (m, 3H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Provided is a compound according to formula I and uses thereof in the preparation of antitumor medications, wherein each substituent group R1, R2, R3, R4, R5, R6 and X are defined as in the Description.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to phenylacetic acid derivatives and their application in the preparation of antitumor drugs. Background technique [0002] Tumor is a new organism formed by the body under the action of various carcinogenic factors, cells lose normal regulation of their growth at the gene level, resulting in abnormal clonal proliferation, manifested as a tumor. Tumor cells are different from normal cells in terms of external morphology, metabolism and function, and most of them present continuous proliferation. According to available statistics, tumor is the first of the three major factors threatening human life and health all over the world, so the research and development of anti-tumor drugs has always been a hot spot. [0003] According to the traditional classification and research progress of antineoplastic drugs, commonly used antineoplastic drugs can be divided into the following catego...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/734C07C69/732C07D317/60C07C59/64C07C59/52C07C235/34A61K31/216A61K31/36A61K31/192A61K31/165A61P35/00
CPCC07C59/52C07C59/64C07C69/732C07C69/734C07C235/34C07D317/60A61P35/00
Inventor 李梢张小虎
Owner JINGPENGHUI PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products