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Quinoline derivative, preparation method and medical use thereof

A derivative, quinoline technology, applied in the field of treating tumor diseases, can solve problems such as signal transduction disorders

Inactive Publication Date: 2009-09-16
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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  • Quinoline derivative, preparation method and medical use thereof
  • Quinoline derivative, preparation method and medical use thereof
  • Quinoline derivative, preparation method and medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] 3-Isopropoxy-4-methylnitrobenzene (1)

[0114] Add 60g (0.39mol) of 3-hydroxy-4-methylnitrobenzene and 100g (0.72mol) of potassium carbonate into a 500ml three-necked flask, dissolve in 300ml of acetone, stir mechanically, and slowly add 50ml of 2-bromopropane ( 0.50mol), react at 40°C for 6 hours. Then the reaction liquid was poured into 1000 ml of water, extracted three times with chloroform, the extract was concentrated, and vacuum-dried to obtain 72.2 g of a brownish-yellow liquid product with a yield of 95%. Molecular formula: C10H13NO3, molecular weight: 195.22

[0115] MS (EI) m / z 195.

Embodiment 2

[0117] 3-isopropoxy-4-methylaniline (2)

[0118] Add 41g (0.73mol) 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-methylnitro Benzene 60g (0.31mol), reacted at 50°C for 2 hours, filtered with suction, combined the filtrates, extracted 3 times with chloroform, concentrated the extract, and dried in vacuo to obtain 45g of a brown oily liquid. Yield 89%. Molecular formula: C10H15NO, molecular weight: 165.24.

[0119] MS (EI) m / z 165.

Embodiment 3

[0121] (Z)-2-Nitryl-3-(3-isopropoxy-4-methylphenyl-amino)-acrylic acid ethyl ester (3)

[0122] Add 45g (0.27mol) of 3-isopropoxy-4-methylaniline, 51g (0.30mol) of (Z)-3-ethoxy-2-nitrile-acrylic acid ethyl ester and 160ml of toluene into a 250ml three-necked flask , heated and stirred, refluxed for 4 hours, cooled to room temperature, a large amount of white solid was precipitated, filtered with suction, recovered toluene in the filtrate, and the filter cake was recrystallized with ethanol to obtain 72 g of the product with a yield of 93%. Molecular formula: C16H20N2O3, molecular weight: 288.35. Mp: 138°C.

[0123] MS (EI) m / z 288.

[0124] 1 H-NMR (AV-500, δ, DMSO-d 6 ): 1.21-1.28(m, 9H); 2.08(s, 3H); 4.14-4.26(t, 2H); 4.55-4.57(m, 1H); 6.81-6.89(m, 2H); 7.01-7.02(d , 1H); 8.26-8.39(t, 1H); 10.58-10.68(d, 1H)

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Abstract

The present invention relates to the field of medicinal chemistry, in particular to a class of 3-cyanoquinoline derivatives (I), a dual inhibitor of tyrosine protein kinase and nitric oxide synthase, wherein G1, G2, G3, G4, X, Z, See the specification for the definition of n. The invention also discloses a preparation method of compound I, a pharmaceutical composition containing it, and an application for treating tumor diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of 3-cyanoquinoline derivatives which are dual inhibitors of tyrosine protein kinase and nitric oxide synthase. The invention also discloses its preparation method and a pharmaceutical composition containing it. And use for treating tumor diseases. 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12C07D401/12A61K31/4709A61P35/00
Inventor 尤启冬曹鑫刘晓蓉李志裕陆小云
Owner CHINA PHARM UNIV
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