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3-Cyanoquinoline derivative, preparation method and medical use thereof

A derivative, quinoline technology, applied in the field of 3-cyanoquinoline derivatives, can solve problems such as signal transduction disorders

Inactive Publication Date: 2007-08-08
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in some cases, as a result of mutations or overexpression, signaling mediated by PTKs is dysregulated

Method used

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  • 3-Cyanoquinoline derivative, preparation method and medical use thereof
  • 3-Cyanoquinoline derivative, preparation method and medical use thereof
  • 3-Cyanoquinoline derivative, preparation method and medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] 3-Isopropoxy-4-methoxynitrobenzene (1)

[0053] Add 60g (0.36mol) of 3-hydroxy-4-methoxynitrobenzene and 100g (0.72mol) of potassium carbonate into a 500ml three-neck flask, dissolve in 300ml of acetone, stir mechanically, and slowly add 90ml of 2-bromopropane dropwise (0.98mol), react at 40°C for 5 hours. Then the reaction solution was poured into 1000ml of water, a large amount of solids were precipitated, and vacuum-dried to obtain 68g of the product, with a yield of 90%. Molecular formula: C10H13NO4, molecular weight: 211.22

[0054] MS (EI) m / z 211.

Embodiment 2

[0056] 3-Isopropoxy-4-methoxyaniline (2)

[0057] Add 40g (0.72mol) of iron powder, 200ml of water, 50ml of acetic acid and 50ml of ethanol into a 500ml three-neck flask, stir and heat to 30°C for 20min, then slowly add 3-isopropoxy-4-methoxy Nitrobenzene 50g (0.24mol), react at 55°C for 3 hours, filter with suction, combine the filtrates, extract 3 times with chloroform, concentrate the extract, and dry in vacuo to obtain 40g of a brown oily liquid. Yield 90%. Molecular formula: C10H15NO2, molecular weight: 181.24.

[0058] MS (EI) m / z 181.

Embodiment 3

[0060] (Z)-2-Nitryl-3-(3-isopropoxy-4-methoxyphenyl-amino)-acrylic acid ethyl ester (3)

[0061] Add 40g (0.22mol) of 3-isopropoxy-4-methoxyaniline, 40g (0.24mol) of (Z)-3-ethoxy-2-nitrile-acrylic acid ethyl ester and 100ml of toluene into 250ml three-neck In the bottle, heated and stirred, refluxed for 6 hours, cooled to room temperature, a white solid was precipitated, filtered with suction, recovered toluene in the filtrate, and the filter cake was recrystallized with ethanol to obtain 48 g of the product with a yield of 75%. Molecular formula: C16H20N2O4, molecular weight: 304.35.

[0062] MS (EI) m / z 304.

[0063] 1 H-NMR (AV-300, δ, DMSO-d 6 ): 1.21-1.28(m, 9H); 3.73(s, 3H); 4.14-4.16(m, 2H); 4.52-4.54(m, 1H); 6.87-6.89(m, 2H); 7.05(s, 1H ); 8.42(s, 1H); 10.58(d, 1H)

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Abstract

The invention discloses a making method of compound I and drug composition and application to treat tumour, which is 3-cyano quinoline derivant (I) as dual-inhibitor protein kinase of tyrosine and nitric oxide synthase, wherein G1, G2, G3, G4, X, Z and n are defined as instruction.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of 3-cyanoquinoline derivatives. The invention also discloses a preparation method of the derivatives and their antitumor application. Background technique [0002] Protein tyrosine kinase (PTK) is a family of protein kinases that can catalyze the transfer of γ-phosphate on ATP or GTP from the donor to the acceptor tyrosine residue of the protein substrate. Cell regulatory processes (e.g. mitosis, cell differentiation, development, tumor formation, angiogenesis, apoptosis, cell formation and adhesion, cell cycle regulation, cell growth regulation, T and B cell activation, response to extracellular stimuli, neural Transmitter signaling, platelet activation, transcriptional regulation, glucose uptake) play an important role. However, in some cases, signaling mediated by PTKs is deregulated as a result of mutations or overexpression. The result of this condition is uncon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D417/14A61K31/4709A61P35/00
Inventor 曹鑫刘晓蓉尤启冬李志裕徐丹
Owner CHINA PHARM UNIV
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