5-[2-hydroxy-3-(alkylamine) propoxy] benzofuran compound and application thereof

A technology of compound and alkoxy group, which is applied in the field of medicine, can solve the problems of different side effects of antihypertensive drugs, and achieve the effect of novel structure type, good development and application prospects, and good application value

Active Publication Date: 2018-03-30
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many kinds of these antihypertensive drugs, and different antihypertensive drugs are adapted to different symptoms, but all antihypertensive drugs have different side effects, and some even cause other complications

Method used

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  • 5-[2-hydroxy-3-(alkylamine) propoxy] benzofuran compound and application thereof
  • 5-[2-hydroxy-3-(alkylamine) propoxy] benzofuran compound and application thereof
  • 5-[2-hydroxy-3-(alkylamine) propoxy] benzofuran compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Preparation of 2-benzoyl-3-methyl-5-[2-hydroxyl-3-(isopropylamino)propoxy]benzofuran (G-01)

[0043] Step A: Preparation of 2'-Hydroxy-5'-Benzyloxyacetophenone

[0044]Put 2',5'-dihydroxyacetophenone (7.60g, 0.05mol), anhydrous potassium carbonate (8.00g, 0.06mol), potassium iodide (1.00g, 0.006mol), and 100mL acetone in a 250mL eggplant-shaped flask , stir well at room temperature. After diluting benzyl chloride (7.87g, 0.06mol) with 10mL of acetone, it was dropped into the reaction solution at a constant speed, and the dropwise addition was completed in about 10 minutes. The reaction was heated to reflux for 6 h, and the reaction was complete as monitored by TLC. After the reaction was completed, it was cooled to room temperature, and the organic solvent was distilled off under reduced pressure to obtain yellow crystals. 50 mL of ethanol was recrystallized to obtain 9.84 g of yellow crystals with a yield of 81.3%. m.p:60.5-63.2℃; EI-MS: 243.0([M+H] + )...

Embodiment 2

[0053] Example 2: Preparation of 2-(4-methoxybenzoyl)-3-methyl-5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran (G-02)

[0054] Referring to the preparation method of Example 1, 1.37 g of light yellow solid was obtained with a yield of 85.3%. m.p: 98.3-100.0℃; ESI-MS: 398.2([M+H] + ); IR: 3076.1, 2967.6, 2923.6, 2836.8, 1639.0, 1604.7, 1562.8, 1508.8, 1451.0, 1384.1, 1365.0, 1319.7, 1238.8, 1206.8, 1178.0, 1102.0, 1027.1; 1 H NMR (400MHz, CDCl 3 )δ8.14 (2H, d, J = 8.6Hz), 7.43 (1H, d, J = 8.9Hz), 7.15-7.07 (2H, m), 7.01 (1H, d, J = 8.5 Hz), 4.17- 4.00(3H,m), 3.90(3H,s), 2.93(1H,d,J=12.0Hz), 2.85(1H,dt,J 1 =12.5,J 2 = 6.2 Hz), 2.79-2.73 (1H, m,), 2.60 (3H, s), 1.11 (6H, d, J = 6.3 Hz).

Embodiment 3

[0055] Example 3: Preparation of 2-benzoyl-3-methyl-5-[2-hydroxyl-3-(tert-butylamino)propoxy]benzofuran (G-03)

[0056] Referring to the preparation method of Example 1, 1.23 g of white solid was obtained with a yield of 79.8%. m.p: 61.7-63.0℃; EI-MS: 382.7([M+H] + ),404.2([M+Na] + ); IR: 3424.4, 3071.2, 2964.9, 2919.9, 2868.2, 1642.5, 1598.9, 1561.7, 1476.7, 1447.5, 1384.8, 1366.6, 1314.1, 1236.8, 1209.6, 1103.5; 1 H NMR (400MHz, CDCl 3 )δ8.07 (2H, d, J = 7.1Hz), 7.60 (1H, t, J = 7.4Hz), 7.51 (2H, t, J = 7.5Hz), 7.42 (1H, d, J = 9.0Hz) ,7.13(1H,dd,J 1 =9.0,J 2 =2.6Hz), 7.09(1H,d,J=2.4Hz), 4.12-3.95(3H,m),2.89(1H,dd,J 1 =11.9,J 2 =3.9Hz), 2.72(1H,dd,J 1 = 11.9,J 2 =7.6Hz), 2.60(3H,s), 1.14(9H,s).

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Abstract

The invention belongs to the technical field of medicines and relates to a 5-[2-hydroxy-3-(alkylamine) propoxy] benzofuran compound and the application thereof. The 5-[2-hydroxy-3-(alkylamine) propoxy] benzofuran compound comprises a stereisomer of the compound and pharmaceutically applicable salt; the general molecular formula of the compound is shown as follows: wherein R is described as the claims and the specification. The 5-[2-hydroxy-3-(alkylamine) propoxy] benzofuran compound and the pharmaceutically applicable acid addition salt of the compound can be combined with the existing drug for use or can be used alone, and are used for preparing a drug for treating a vascular smooth muscle spastic disease.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to 5-[2-hydroxy-3-(alkylamino)propoxy]benzofuran compounds and applications thereof. The compounds can be used as drugs for treating vascular smooth muscle spasm diseases. Background technique: [0002] Hypertension is one of the most important public health problems in the world today, but the awareness rate, treatment rate and control rate of hypertension diagnosis and treatment are all low. In the adult population of western developed countries, the incidence of hypertension is 30% to 40%, and it increases with age. In developing countries, the incidence of high blood pressure is higher. my country's epidemiological survey data recorded the prevalence of hypertension in the past 50 years, from 5% in 1959, 7% in 1979, 18.8% in 2008 to about 21% reported in recent years, the prevalence increased The number of patients has increased by about 4 times, reaching 200 million. At pres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80A61K31/343A61P9/12A61P9/10A61P9/04A61P13/12A61P9/00
CPCC07D307/80
Inventor 胡春郭万欣王琳金丽萍黄二芳金辄王海明周国军杨俊渠冰雪
Owner SHENYANG PHARMA UNIVERSITY
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