Ferulic acid derivatives, preparation and application of ferulic acid derivatives

A technology of ferulic acid and derivatives is applied in the application field of ferulic acid derivatives in the prevention and/or treatment of stroke-related diseases, and can solve the problems of limited treatment means and great harm of stroke.

Active Publication Date: 2016-06-22
江苏冠瑜生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, in view of the great harm of stroke and the extremely limited current treatment methods, the development of new drugs for the prevention and / or treatment of stroke has always been the focus of extensive attention of frontier scholars in this field, which is of great significance

Method used

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  • Ferulic acid derivatives, preparation and application of ferulic acid derivatives
  • Ferulic acid derivatives, preparation and application of ferulic acid derivatives
  • Ferulic acid derivatives, preparation and application of ferulic acid derivatives

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preparation example Construction

[0038] The present invention has no special limitation on the preparation method of the ferulic acid derivatives, the preparation method of this type of compound known to those skilled in the art can be used, and those skilled in the art can select and adjust according to the actual situation and product requirements. , the ferulic acid derivatives described in the present invention are preferably ester compounds of ferulic acid and ADTO (CH 2 ) z X (z = 3 ~ 10, X is a halogen) obtained after the reaction, specifically ethyl ferulate and ADTO (CH 2 ) z Obtained after Br reaction.

[0039] The present invention provides an application of the ferulic acid derivative described in any one of the above technical solutions in the preparation of drugs for the prevention and / or treatment of cerebral apoplexy.

[0040] In the present invention, the ferulic acid derivative is preferably the above-mentioned compound having the structure of formula I or formula II, more specifically 3-...

Embodiment 1

[0054] 3-Methoxy-4-{3-[4-(3H-1,2-dithiol-3-thiol-5-yl)phenoxy]propoxy}ethyl phenylacrylate ( SYX-I 1 )Synthesis

[0055] (E)-Ethyl 4-hydroxy-3-methoxyphenylacrylate (222 mg, 1 mmol), 5-[4-(3-bromopropoxy)-phenyl]-[1,2]-di Thiolene-3-thione (347mg, 1mmol), KI (17-34mg, 0.1-0.2mmol), and potassium carbonate (139mg, 1mmol) were added to acetone, and refluxed at 100°C for 8h. After the reaction, filter with suction, mix the sample to pass through the column, perform column chromatography, and eluate (petroleum ether: ethyl acetate = 8:1). A yellow powdery solid was obtained. Yield 68%.

[0056] 1 HNMR (400MHz, CDCl 3 ), 7.06(s,1H,ArH),6.99(d,J=8.8Hz,2H,ArH),6.90(d,J=8.2Hz,1H,ArH),6.31(d,J=15.9Hz,1H,C= CH),4.29–4.21(m,6H,OCH 2 ),3.88(s,3H,OCH 3 ),2.36(p,J=6.0Hz,2H,CH 2 ), 1.34(t, J=7.1Hz, 3H, CH 3 ).

[0057] 13 CNMR (400MHz, CDCl 3 )δ215.10,172.96,167.17,162.17,150.22,149.53,144.35,134.62,128.56,127.79,124.21,122.39,116.15,115.46,112.69,110.09,65.23,64.78,60.38,55.8...

Embodiment 2

[0060] Ethyl 3-methoxy-4-{4-[4-(3H-1,2-dithiol-3-thiol-5-yl)phenoxy]butoxy}phenylacrylate ( SYX-I 2 )Synthesis

[0061] Prepared with reference to the method of Example 1 from ethyl ferulate and 5-(4-(4-bromobutoxy)phenyl)-1,2-dithiole-3-thione to obtain a yellow powder shaped solid. Yield 65%.

[0062] 1 HNMR (400MHz, CDCl 3 ), 7.05(d, J=1.8Hz, 1H, ArH), 6.96(d, J=8.8Hz, 2H, ArH), 6.87(d, J=8.3Hz, 1H, ArH), 6.31(d, J=15.9Hz ,1H,C=CH),4.26(q,J=7.1Hz,2H,OCH 2 ), 4.13 (q, J=5.6Hz, 4H, OCH 2 ),3.88(s,3HOCH 3 ),2.12–1.99(m,4H,CH 2 ), 1.34(t, J=7.1Hz, 3H, CH 3 ).

[0063] 13 CNMR (400MHz, CDCl 3 )δ215.08,173.04,167.20,162.34,150.37,149.47,144.42,134.56,128.54,127.54,124.04,122.45,116.00,115.40,112.38,110.00,68.41,67.91,60.37,55.88,25.91,25.67,14.34.

[0064] LC-MS: Calcd.ForC 25 h 26 o 5 S 3 [M+H] + 503.1021, Found: 503.1037.

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Abstract

The invention provides ferulic acid derivatives adopting a structure shown in formula I or formula II. Starting from the mechanism of various mechanisms causing brain injury after cerebral stroke and the action of ferulic acid in treatment of the cerebral stroke, alkane is taken as a joint arm, ADT-OH (5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione) and ferulic acid are connected through ether linkage and ester linkage, and the ferulic acid derivatives are obtained. The invention further provides the application of the ferulic acid derivatives in preparation of drugs for preventing and/or treating cerebral stroke diseases.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a ferulic acid derivative, a preparation and its application, in particular to the application of a ferulic acid derivative in medicines for the prevention and / or treatment of stroke diseases. Background technique [0002] "Stroke" (cerebralstroke) is also known as "stroke" and "cerebrovascular accident" (cerebralvascularaccident, CVA). It is an acute cerebrovascular disease, which is a group of diseases that cause brain tissue damage due to sudden rupture of blood vessels in the brain or blockage of blood vessels that prevent blood from flowing into the brain. [0003] Worldwide, stroke is the third leading cause of death and the leading cause of disability in adults. According to statistics, 500,000 to 750,000 people in the United States develop the disease every year. In China, the incidence of cerebral apoplexy reaches 2.5 million / year, and the death toll reaches 1.6 mill...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04A61K31/385A61P9/10
CPCC07D339/04
Inventor 敖桂珍程坚贾佳孙银星李玉姚
Owner 江苏冠瑜生物科技有限公司
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