Medicine use of beta-methoxy acrylic ester compounds as novel STAT3 restrainer

A compound, the technology of isopropoxy, which is applied in the field of β-methoxyacrylate, can solve the problems that there are no STAT3 inhibitors of β-methoxyacrylate

Inactive Publication Date: 2008-09-24
INST OF RADIATION MEDICINE ACAD OF MILITARY MEDICAL SCI OF THE PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports of β-methoxyacrylate STAT3 inhibitors

Method used

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  • Medicine use of beta-methoxy acrylic ester compounds as novel STAT3 restrainer
  • Medicine use of beta-methoxy acrylic ester compounds as novel STAT3 restrainer
  • Medicine use of beta-methoxy acrylic ester compounds as novel STAT3 restrainer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 (E)-3-methoxy-2-[2-(2-isopropoxy-6-trifluoromethylpyrimidine-4-oxyl group) phenyl] methyl acrylate (compound 1, Fluacrypyrim , FAPM) preparation

[0034] (1) Methyl o-tolylacetic acid: Weigh 7.5g (0.05mol) o-tolylacetic acid, dissolve it in 75mL of anhydrous methanol, add 0.1mL of sulfuric acid under stirring, heat and reflux for 2 hours, then cool and depressurize Recover the solvent, add 30mL of dichloromethane and 20mL of water, separate the layers, extract the water layer once with 15mL of dichloromethane, combine the dichloromethane solution, wash with water once, dry over anhydrous sodium sulfate, filter off the solid, and recover the solvent. A colorless liquid was obtained. It can be directly used in the next reaction.

[0035] (2) 3-Hydroxy-2-(2-methylphenyl)-2-methyl acrylate: Weigh 2.50g (0.062mol) of sodium hydride, suspend in 25mL of dry tetrahydrofuran, add under ice water cooling and stirring 20 mL of methyl formate dried over anhydrous sodiu...

experiment example 2

[0041] Experimental example 2 (E)-3-methoxy-2-[2-(3,4-dihydro-2-isopropoxy-4-oxo-6-trifluoromethylpyrimidin-1-yl)benzene base] the preparation of methyl acrylate (compound 2, IFAPM)

[0042] (1)-(6) steps are the same as the preparation of compound 1, and the operation of step (7) is basically the same as that of compound 1, except that the target product to be separated is the second (rear) main point after column chromatography separates compound 1, Yield 5.85g, mp 94-96°C. 1H-NMR (CDCl3, ppm) δ: 1.089 (br-s, 6H), 3.621 (s, 3H), 3.843 (s, 3H), 4.90 (br-s, 1H), 5.231 (m, 2H), 6.457 (s, 1H), 7.09-7.15 (m, 2H), 7.24-7.29 (m, 2H), 7.484 (s, 1H).

[0043] The following biological activity experiments are used to further illustrate the present invention.

[0044] Biological effect experiment 1 Effect of FAPM on the expression levels of STAT family, PI3 / Akt and MAPK signaling pathway signaling molecules in cells

[0045] figure 1 Shown is the effect of FAPM on the expression l...

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PUM

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Abstract

The invention relates to the application of compounds possessing STAT3 inhibitor activity shown in general formula I, isomers and a drug compound containing the compounds and isomers in the prevention or treatment of malignant tumors, AIDS and inflammations and the termination of unexpected pregnancies or the application of tool drugs used for studying the growth, proliferation, differentiation and apoptosis of tumors as well as STAT3-related signaling pathways.

Description

technical field [0001] The present invention relates to the application of β-methoxyacrylate with STAT3 inhibitory activity, its isomers, and pharmaceutical compositions containing them in the prevention or treatment of malignant tumors, AIDS and inflammation, and termination of unwanted pregnancy, or Application as a tool drug for studying tumor growth, proliferation, differentiation and apoptosis, and STAT3-related signal transduction pathways. Background technique [0002] β-methoxyacrylate is a new class of fungicides, mainly used in agriculture (such as grains, fruits and vegetables, etc.) to kill fungi. The earliest natural products, such as strobilurin, the simplest is strobilurin A (Strobilurin). Afterwards, chemical synthesis products appeared successively, such as Azoxystrobin (Azoxystrobin) and Picoxystrobin (Picoxystrobin), and Fluacrypyrim (Fluacrypyrim, FAPM). Among them, pyrimaben FAPM is an acaricide and nematocide, mainly used in vegetables and fruits. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/505A61K31/216A61P35/00A61P31/18A61P29/00C07D239/52
Inventor 从玉文杨日芳余祖胤善亚君黄锐赵振虎陈家佩
Owner INST OF RADIATION MEDICINE ACAD OF MILITARY MEDICAL SCI OF THE PLA
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