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Application of 2-aza-arene-substituted quinazoline compound to preparation of antitumor drug

An anti-tumor drug, quinazoline technology, which is applied in the field of medicine, can solve problems such as the difficulty in the synthesis of quinazoline compounds, and achieve the effects of simple and efficient preparation methods, easy-to-obtain raw materials, and great application value

Active Publication Date: 2020-09-25
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the quinazoline compounds substituted with 2-position azaarene are difficult to synthesize, so their activity studies have not been reported yet.

Method used

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  • Application of 2-aza-arene-substituted quinazoline compound to preparation of antitumor drug
  • Application of 2-aza-arene-substituted quinazoline compound to preparation of antitumor drug
  • Application of 2-aza-arene-substituted quinazoline compound to preparation of antitumor drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]

[0044] 4-(4-fluorophenyl)-2-(quinolin-2-yl)-quinazoline: 74% yield, 1 H NMR (400MHz, CDCl 3 ) δ8.85(d, J=8.5Hz, 1H), 8.44(dd, J=18.6, 8.4Hz, 2H), 8.35(d, J=8.3Hz, 1H), 8.15(d, J=8.1Hz, 1H), 7.96(s, 3H), 7.88(d, J=7.7Hz, 1H), 7.77(t, J=7.4Hz, 1H), 7.66-7.58 (m, 2H), 7.31(t, J=8.3 Hz,2H). 13 C NMR (100MHz, CDCl 3 )δ167.6,163.9(d,J=248.9 Hz),159.0,155.1,151.9,148.2,136.8,133.7,133.3,132.3,132.2,130.7,129.9,129.5,128.4,128.1,1267.3,116.39,112 (d, J = 21.5 Hz).

Embodiment 2

[0046]

[0047] 4-Phenyl-2-(quinolin-4-yl)-quinazoline: 73% yield, 1 H NMR (400MHz, CDCl 3 )δ9.09 (d, J = 4.4Hz, 1H), 8.89 (d, J = 8.1Hz, 1H), 8.24 (t, J = 9.0Hz, 3H), 8.16 (d, J = 4.4Hz, 1H) , 8.01–7.95(m,1H),7.89(dd,J=6.6,2.9Hz,2H),7.79–7.74(m,1H),7.71–7.57(m,5H). 13 C NMR (100MHz, CDCl 3 )δ 168.8, 160.5, 151.5, 150.0, 149.1, 144.0, 137.0, 134.1, 130.2, 130.1, 129.8, 129.3, 128.7, 128.3, 127.2, 127.1, 126.3, 126.0, 122.8, 121.6.

Embodiment 3

[0049]

[0050] 4-Phenyl-2-(5-methylpyridin-2-yl)-quinazoline: 50% yield, 1 H NMR (400MHz, CDCl 3 )δ 8.74(s,1H),8.66(d,J=7.9Hz,1H),8.35(d,J=8.3Hz,1H),8.14(d,J=8.3Hz,1H),7.94 –7.86(m ,3H),7.68(d,J=7.6Hz,1H),7.58(s,4H),2.44(s,3H). 13 C NMR (101MHz, CDCl 3 )δ 168.7, 159.2, 152.7, 152.0, 150.7, 137.4, 137.4, 134.6, 133.7, 130.2, 129.9, 129.8, 128.5, 127.6, 126.9, 123.9, 122.1, 18.5.

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Abstract

The invention discloses an application of a 2-aza-arene-substituted quinazoline compound to preparation of an antitumor drug. The structure of the 2-aza-arene-substituted quinazoline compound is as shown in a formula (I), wherein R<1> is hydrogen, C1-6 alkyl, substituted C1-6 alkyl, C5-6 aryl, substituted C5-6 aryl or C9-10 fused bicyclic aryl; R<2> is C1-6 alkyl, substituted C1-6 alkyl, C5-6 aryl, substituted C5-6 aryl or C9-10 fused bicyclic aryl; and aza-arene is C5-6 aza-aryl, substituted C5-6 aza-aryl or C9-10 fused bicyclic aza-aryl. The 2-aza-arene-substituted quinazoline compound disclosed by the invention shows a certain inhibitory effect on breast cancer cells, colon cancer cells and hepatic carcinoma cells, the inhibitory effect of partial structure on the colon cancer cells andthe hepatic carcinoma cells is particularly significant, or even significantly better than that of a positive control drug, and the 2-aza-arene-substituted quinazoline compound can be prepared into the antitumor drug for the application. Meanwhile, the 2-aza-arene-substituted quinazoline compound is simple and efficient in preparation method and available in raw material, can achieve industrial production and has great application value in anti-tumor application.

Description

technical field [0001] The present invention relates to the technical field of medicine, and more specifically relates to the application of 2-position azaarene substituted quinazoline compounds in the preparation of antitumor drugs. Background technique [0002] Cancer has become a disease that seriously endangers human health, and it is also the second largest killer after cardiovascular disease. At present, clinical anticancer drugs mainly include alkylating agents, antimetabolite drugs, antitumor antibiotics, antitumor herbal medicines and immunotherapy drugs, etc., but many anticancer drugs have obvious toxic side effects on normal organisms, such as mutagenicity, genetic Toxicity, etc., so the study of anticancer drugs has become a hot topic today. At present, the structures of anti-tumor drugs are complex and diverse, and compounds with different structures show excellent anti-tumor activities. Finding effective anti-tumor drugs with new structures and less toxic si...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/517A61P35/00
CPCA61K31/517A61P35/00Y02P20/55
Inventor 吴婷唐晓冬梁恩石杰
Owner SOUTHERN MEDICAL UNIVERSITY
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