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Quinazoline derivative and application thereof as vasculogenesis inhibitor

An angiogenesis inhibition and derivative technology, which can be used in drug combination, organic chemistry, anti-tumor drugs, etc., and can solve problems such as drug resistance, adverse reactions, and application limitations.

Inactive Publication Date: 2014-04-30
李增
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because anti-tumor chemotherapy drugs often have serious adverse reactions and drug resistance problems, their application is greatly limited, so angiogenesis inhibitors are increasingly concerned by humans as new anti-tumor drugs

Method used

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  • Quinazoline derivative and application thereof as vasculogenesis inhibitor
  • Quinazoline derivative and application thereof as vasculogenesis inhibitor
  • Quinazoline derivative and application thereof as vasculogenesis inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis of compound 2

[0020]

[0021] Dissolve 521.6mmol of dry o-nitrobenzoic acid in 60ml of thionyl chloride, evaporate the thionyl chloride after reflux for 2h, and slowly add the obtained brown liquid dropwise to 727.7mmol of anthranilic acid in an ice bath. Formamide and 1455.4 mmol of triethylamine in chloroform (250 ml) were stirred overnight at room temperature, filtered, and washed with ethanol to give 2 as a white solid, yield: 79%. 1 H NMR(400MHz,DMSO)δ12.57(s,1H),8.53(d,J=8.2Hz,1H),8.43(s,1H),8.13(d,J=8.3Hz,1H),7.95–7.78 (m,5H),7.62(dd,J=11.4,4.0Hz,1H),7.29–7.22(m,1H).

Embodiment 2

[0022] Embodiment two: the synthesis of compound 3

[0023]

[0024] After mixing 357.2mmol of dry 2 with 80ml of 10% aqueous sodium hydroxide solution and 80ml of ethanol, they were reacted at 95°C for 6 hours. Ethanol was distilled off, and the pH value of the solution was adjusted to 3 with HCl. A large amount of white solid was precipitated, filtered and dried, and purified by silica gel chromatography (petroleum ether: ethyl acetate = 3:1) to obtain 3 as a white solid with a yield of 91%. 1 HNMR(400MHz,DMSO)δ12.86(s,1H),8.27–8.16(m,2H),7.95–7.81(m,4H),7.67(d,J=7.8Hz,1H),7.62–7.56(m ,1H).

Embodiment 3

[0025] Embodiment three: the synthesis of compound 4

[0026]

[0027] Dissolve 0.0314 mmol of dry 3 in 80 ml of toluene, add 5-10 times molar amount of phosphorus oxychloride and equimolar amount of N,N-diethylaniline, and react under reflux at 105°C for 5 hours. After the reaction, wash with equal volumes of the following solutions in sequence: water, 20% aqueous sodium hydroxide solution (twice), water, saturated saline, 1M hydrochloric acid, and water. The light red flocculent solid precipitated during the washing process was filtered out, filtered, washed with ethanol, and purified by silica gel chromatography (chloroform:methanol=3:1) to obtain white solid 4 with a yield of 74%. 1 H NMR (400MHz,DMSO)δ8.22(ddd,J=16.6,8.0,1.0Hz,2H),7.97–7.82(m,4H),7.69(d,J=7.7Hz,1H),7.63–7.58( m, 1H).

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Abstract

The invention discloses a quinazoline derivative and an application thereof as a vasculogenesis inhibitor. The quinazoline derivative has an obvious inhibitory effect on HUVEC cell proliferation and vasculogenesis, and can be used as a vasculogenesis inhibitor. The quinazoline derivative disclosed by the invention has an inhibitory effect on invasion and metastasis and vasculogenesis, and can be used for preparing a medicine for treating the diseases related to tumor vasculogenesis and other vasculogenesis.

Description

technical field [0001] The invention mainly relates to the technical field of new drug research and development, in particular to a quinazoline derivative method and its application as an angiogenesis inhibitor. Background technique [0002] Cancer is a common and frequently-occurring disease that seriously threatens human health and life, and it is also one of the most difficult diseases to treat, second only to cardiovascular and cerebrovascular diseases as the second cause of human death. Tumor treatment methods include surgical treatment, radiotherapy and drug therapy, and drug therapy is mainly used in clinical practice at present. Because anti-tumor chemotherapy drugs often have serious adverse reactions and drug resistance problems, their application is greatly limited, so angiogenesis inhibitors are increasingly concerned by humans as new anti-tumor drugs. [0003] The formation of the vascular system in the human body has two processes: angiogenesis (Vasculogenesis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/94A61P35/00
CPCC07D239/94
Inventor 李增俞广进
Owner 李增
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