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3-benzyl-4-quinazolinone compound as well as synthetic method and applications thereof

A quinazolinone and compound technology, which is applied in the field of 3-benzyl-4-quinazolinone compound and its synthesis, can solve the problems of short action time, weak drug effect and high production cost, and can reduce systolic blood pressure , The synthesis method is easy, and the effect achieved by the synthesis method

Active Publication Date: 2014-01-22
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Amlodipine, lacidipine and felodipine have the characteristics of high efficiency and long-acting, and can be taken orally once a day to obtain a satisfactory antihypertensive effect, but the production cost is relatively high; nifedipine and nitrendipine have simple structures and are easy to use. Synthetic, but both have weak efficacy and short action time, and need to be taken orally 3 times a day

Method used

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  • 3-benzyl-4-quinazolinone compound as well as synthetic method and applications thereof
  • 3-benzyl-4-quinazolinone compound as well as synthetic method and applications thereof
  • 3-benzyl-4-quinazolinone compound as well as synthetic method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13-（4

[0055] Preparation of Example 13-(4-methoxybenzyl)-7-fluoro-4-quinazolinone (1)

[0056]Add absolute ethanol (10mL), 2-amino-4-fluorobenzoic acid (0.23g), 4-methoxybenzylamine (0.20g), triethyl orthoformate (0.6mL) into a 50mL round bottom flask , the mixture was stirred and refluxed for 5 h under the protection of nitrogen, the solvent was distilled off under reduced pressure, and the residue was separated by silica gel column chromatography (chloroform:methanol=50:1). 1 H NMR (CDCl 3 ,400MHz),δ:3.79(3H,s,OCH 3 ),5.12(2H,s,Ar-CH 2 ), 6.88(2H,d,J=7.6Hz,Ar-H),7.22(1H,t,J=8.4Hz,Ar-H),7.30(1H,s,Ar-H),7.34(2H,d , J=10.0Hz, Ar-H), 8.11 (1H, s, Ar-H), 8.33 (1H, t, J=8.0Hz, Ar-H).

Embodiment 23-（4

[0057] Example 2 Preparation of 3-(4-methoxybenzyl)-7-chloro-4-quinazolinone (2)

[0058] 2-amino-4-chlorobenzoic acid was used instead of 2-amino-4-fluorobenzoic acid, isopropanol was used instead of absolute ethanol, and the reflux reaction time was 8 hours. The rest of the operations were the same as in Example 1. 1 H NMR (CDCl 3 ,400MHz),δ:3.79(3H,s,OCH 3 ),5.12(2H,s,Ar-CH 2 ),6.88(2H,d,J=7.6Hz,Ar-H),7.31(2H,d,J=7.6Hz,Ar-H),7.45(1H,d,J=8.4Hz,Ar-H), 7.71 (1H, s, Ar-H), 8.28 (2H, d, J=8Hz, Ar-H).

Embodiment 33-（4

[0059] Example 3 Preparation of 3-(4-methoxybenzyl)-6-bromo-4-quinazolinone (3)

[0060] 2-amino-5-bromobenzoic acid was used instead of 2-amino-4-fluorobenzoic acid, 2-methoxyethanol was used instead of ethanol, the reflux reaction time was 3 hours, and the rest of the operations were the same as in Example 1. 1 H NMR (CDCl 3 ,400MHz),δ:3.81(3H,s,OCH 3 ),5.16(2H,s,Ar-CH 2 ),6.90(2H,d,J=8.0Hz,Ar-H),7.33(2H,d,J=8.0Hz,Ar-H),7.62(1H,d,J=8.4Hz,Ar-H), 7.85 (1H, d, J=8.8Hz, Ar-H), 8.16 (1H, s, Ar-H), 8.45 (1H, s, Ar-H).

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Abstract

The invention discloses a 3-benzyl-4-quinazolinone compound as well as a synthetic method and applications thereof. The compound is novel in structure and the synthetic method of the compound is easy to realize. Vascular ring tension experiments show that the compound has remarkable vasodilation activity, and gavage administration shows that the compound can remarkably lower the systolic pressure of SD (Sprague Dawley) rats. The compound can be used for preparing antihypertensive medicines as well as medicines for treating cardiovascular diseases.

Description

technical field [0001] The invention belongs to the technical field of antihypertensive drugs, and relates to 3-benzyl-4-quinazolinone compounds and their synthesis methods and applications. Background technique [0002] At present, about 3 million people die from cardiovascular diseases in my country every year, accounting for 40% of all causes of death. Cardiovascular disease is the number one killer of Chinese residents. With the improvement of people's living standards and the aging of the population, the incidence of cardiovascular diseases, especially hypertension, is increasing day by day. According to statistical data, the incidence of hypertension among people aged 35 to 74 in my country is as high as 27%, and the number of patients is close to 160 million, with an increase of more than 3 million every year. Hypertension has become the most common cardiovascular disease in the world, and it is also one of the largest epidemics. It often causes complications in the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91C07D405/06A61K31/517A61P9/00A61P9/12
CPCC07D239/91C07D405/06C07D491/056
Inventor 曹永孝张三奇左赛杰李森傅强耿庆光刘静
Owner XI AN JIAOTONG UNIV
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