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Phenylpropionate compound and preparation method and application thereof

A technology of phenylpropionate and phenylacrylate, which is applied in the field of phenylpropionate compounds and their preparation, and can solve problems such as not being able to exhibit ideal drug effects

Active Publication Date: 2018-05-18
SUZHOU PHARMAVAN CANCER RES CENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of treating stroke, the drug also needs to pass through the blood-brain barrier and reach the effective concentration to be effective. However, most drug molecules cannot penetrate the blood-brain barrier to reach the brain. Therefore, many drugs for the treatment of brain diseases Some drugs can show good drug-target binding activity in in vitro tests, but they can't show ideal drug effects in animal tests

Method used

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  • Phenylpropionate compound and preparation method and application thereof
  • Phenylpropionate compound and preparation method and application thereof
  • Phenylpropionate compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] The synthesis of embodiment 1 formula A compound

[0088] (1) Under nitrogen protection, mono(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol ester (11.5g, 47.9mmol) , 3-fluoro-4-hydroxyl-5-methoxybenzaldehyde (7.3g, 42.9mmol) was added in toluene (100ml), added pyridine (7.6g, 95.8mmol), piperidine (0.4g, 4.7mmol) , heated up to 120°C for 5 hours, after the reaction, let the reaction liquid cool, and washed with 1N hydrochloric acid solution, saturated NaHCO 3 solution, washed with saturated NaCl solution, dried over anhydrous sodium sulfate for 4h, concentrated to dryness, and recrystallized from ethyl acetate / petroleum ether to obtain (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2. 1] Heptane-2-yl (E)-3-(3-fluoro-4-hydroxy-5-methoxyphenyl)acrylate white powder solid 10.2g, yield 68.5%. EI-MS M / Z349.2[M + ], 347.3[M - ].

[0089] 1 H-NMR (CDCl 3 ,500MHz) 0.78 (3H, s, H-12), 0.86, 0.87 (each 3H, s, H-13, 14), 0.89 (1H, d, H-8α), 1.14 (1H, m, H-10β ),1.17~1.21(1H,t,H...

Embodiment 2

[0091] The synthesis of embodiment 2 formula A compound

[0092] (1) Under nitrogen protection, mono(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol ester (5.3g, 22.1mmol) , 3-fluoro-4-hydroxyl-5-methoxybenzaldehyde (3.0g, 17.6mmol) was added in toluene (50ml), piperidine (0.38g, 4.4mmol), acetic acid (0.26g, 4.4mmol) were added , heated up to 120°C for 5 hours, after the reaction, let the reaction liquid cool, and washed with 1N hydrochloric acid solution, saturated NaHCO 3 solution, washed with saturated NaCl solution, dried over anhydrous sodium sulfate for 4h, concentrated to dryness, and recrystallized from ethyl acetate / petroleum ether to obtain (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2. 1] Heptan-2-yl (E)-3-(3-fluoro-4-hydroxy-5-methoxyphenyl)acrylate white powder solid 4.3g, yield 70.5%.

[0093] (2) At room temperature, (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-yl(E)-3-(3-fluoro-4- Hydroxy-5-methoxyphenyl) acrylate (1.0g, 2.9mmol) was added in methanol (20m...

Embodiment 3

[0094] The synthesis of embodiment 3 formula B compound

[0095] (1) Under nitrogen protection, mono(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol ester (11.5g, 47.9mmol) , 3,4-dihydroxy-5-methoxybenzaldehyde (7.2g, 42.9mmol) was added to toluene (100ml), pyridine (7.6g, 95.8mmol) and piperidine (0.4g, 4.7mmol) were added, Raise the temperature to 120°C and react for 5 hours. After the reaction, let the reaction solution cool down, and wash with 1N hydrochloric acid solution, saturated NaHCO 3 solution, washed with saturated NaCl solution, dried over anhydrous sodium sulfate for 4h, concentrated to dryness, and recrystallized from ethyl acetate / petroleum ether to obtain (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2. 1] Heptan-2-yl (E)-3-(3,4-hydroxy-5-methoxyphenyl)acrylate white powder solid 8.3g, yield 55.8%. EI-MS M / Z 347.2[M + ], 345.2[M - ].

[0096] (2) At room temperature, (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-yl (E)-3-(3,4-hydroxyl- 5-Methoxyphenyl) acr...

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Abstract

The invention provides a phenylpropionate compound and a preparation method and application thereof. The phenylpropionate compound is of a structure shown in the formula I. The phenylpropionate compound, pharmaceutically acceptable salts, solvates, prodrugs, tautomers or stereochemical isomers or pharmaceutical compositions of the phenylpropionate compound have better anti-inflammatory and anti-platelet effects and the like, a longer therapeutic time window at the same time and no obvious side effects, are safe and effective, can be used as anti-thrombotic drugs, anti-inflammatory drugs and cerebral apoplexy treatment drugs, and have a wide range of application prospects.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and relates to a phenylpropionate compound and its preparation method and application. Background technique [0002] Stroke is a disease in which brain tissue is damaged due to sudden rupture of blood vessels in the brain or blood circulation disorder caused by blood vessel blockage. Ischemic stroke refers to the necrosis of local brain tissue including nerve cells, glial cells and blood vessels due to lack of blood supply. [0003] According to the "China Cardiovascular Disease Report 2013", the prevalence of cerebrovascular diseases in my country is on the rise. According to the 2010 Global Burden of Disease Study, stroke is the third leading cause of disability-adjusted life years (DALYs). At the same time, stroke is the second leading cause of death among people over 60 years old, and it is one of the neurological diseases with the highest fatality rate. In my country, strok...

Claims

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Application Information

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IPC IPC(8): C07C69/734A61K31/216A61P9/10
CPCC07C69/734C07C69/736C07C2602/42C07C67/303C07C67/343A61P9/10C07B2200/07
Inventor 刘乾李云森邓世平高原娄山宁俞云会江传亮
Owner SUZHOU PHARMAVAN CANCER RES CENT CO LTD
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