Cinnamamide derivative and application as cerebral nerve protective agent

A technology of cinnamamide and derivatives, applied in the field of substituted cinnamamide derivatives and brain neuroprotectants, can solve the problems of low selectivity, poor oral bioavailability, high neurobehavioral toxicity and the like

Inactive Publication Date: 2010-06-30
NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] One of the technical problems to be solved in the present invention is to disclose a new substituted cinnamic amide derivative with medical value, so as to overcome the existing problems of the prior art, such as induced hemorrhage, difficulty in penetrating the blood-brain barrier, poor oral bioavailability, Defects such as low selectivity and high neurobehavioral toxicity

Method used

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  • Cinnamamide derivative and application as cerebral nerve protective agent
  • Cinnamamide derivative and application as cerebral nerve protective agent
  • Cinnamamide derivative and application as cerebral nerve protective agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (E)-3-(3,4-diacetoxyphenyl)acrylic acid

[0043]Add 3,4-dihydroxybenzaldehyde (13.8g, 0.1mol), malonic acid (15.6g, 0.15mol), pyridine (68ml), hexahydropyridine ( 1.8ml), heated to 95°C for 3 hours. After cooling, the solvent was evaporated under reduced pressure, and the residue was poured into a mixture of concentrated hydrochloric acid (68ml) and ice (150ml) and stirred to precipitate an off-white solid. Filtration and recrystallization from absolute ethanol yielded 6.4 g of off-white powder caffeic acid, yield 35.2%, mp 205.9-209.5°C.

[0044] Add caffeic acid (5.2g, 0.029mol), acetic anhydride (24ml), and pyridine (20ml) into the reaction flask, and stir overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was poured into ice water to obtain a pale yellow solid, which was recrystallized from absolute ethanol to obtain 6.5 g of a white solid, yield 85.9%, mp 197.1-199.7°C.

Embodiment 2

[0046] (E)-3-(3-methoxy-4-acetoxyphenyl)acrylic acid

[0047] The preparation method is the same as in Example 1. Vanillin (15.2g, 0.1mol), malonic acid (15.6g, 0.15mol), pyridine (68ml), and hexahydropyridine (1.8ml) are heated to 95°C for reaction to obtain A Ferulic acid 9.2g, yield 47.4%, mp170.7-172.4°C.

[0048] Ferulic acid (5.6g, 0.029mol), acetic anhydride (12ml), and pyridine (20ml) were reacted at room temperature to obtain 6.1g of white solid, yield 89.1%, mp 168.5-169.9°C.

Embodiment 3

[0050] (E)-3-(4-fluorophenyl)acrylic acid

[0051] The preparation method is the same as in Example 1, 4-fluorobenzaldehyde (12.4g, 0.1mol), malonic acid (15.6g, 0.15mol), pyridine (68ml), hexahydropyridine (1.8ml), heated to 95°C for reaction, 13 g of white solid was obtained, yield 78.3%, mp 209.1-210.8°C.

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PUM

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Abstract

The invention discloses a substituted cinnamamide derivative and the application of the cinnamamide derivative as the cerebral nerve protective agent in pharmacy. The substituted cinnamamide derivative provided by the invention includes free alkali or salt of a compound presented by the formula (I). The compound of the invention shows therapeutic action on the animal cerebral ischemia model and protective action on the cerebral nerves after cerebral ischemic stroke, and can be used for preparing the cerebral nerve protective agent after cerebral ischemic stroke and for treating cerebral ischemic stroke.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a new substituted cinnamic amide derivative and the use of the derivative as a brain neuroprotective agent. Background technique [0002] Stroke is one of the diseases with the highest mortality and disability rate today, and nearly 80% of strokes are ischemic strokes. The survival of brain cells after a stroke depends on how much neurons are damaged, that is, how much blood flow to the brain that supplies cells with oxygen and nutrients is reduced. When ischemic stroke occurs, the cerebral blood flow in the ischemic core is severely reduced, and irreversible damage occurs to the brain tissue after 60-90 minutes; while the cerebral blood flow in the peripheral ischemic penumbra of the core is relatively reduced, but the cell metabolism Within a few hours after the occurrence of ischemia, the abnormal electrical activity and metabolic disorder in the ischemic area form a chain reaction, whi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185C07D317/60A61K31/495A61K31/496A61P9/10
Inventor 吴斌许逸李萍张晓平李飞王秀珍
Owner NANJING MEDICAL UNIV
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