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Substituted cinnamamide derivatives and application of the same as nerve protecting agent

A compound and benzo-based technology, which can be used in medical preparations containing active ingredients, drug combinations, cardiovascular system diseases, etc., and can solve problems such as non-disclosure

Inactive Publication Date: 2012-09-05
NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no disclosure of substituted cinnamic acid derivatives condensed with benzhydrylpiperazine compounds to form substituted cinnamic amide derivatives, and there is no report on whether these substituted cinnamic acid amide derivatives have neuron protection and cerebral apoplexy therapeutic activity

Method used

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  • Substituted cinnamamide derivatives and application of the same as nerve protecting agent
  • Substituted cinnamamide derivatives and application of the same as nerve protecting agent
  • Substituted cinnamamide derivatives and application of the same as nerve protecting agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (E)-3-(3,4-diacetoxyphenyl)acrylic acid

[0042] 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.

[0043] 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

[0045] (E)-3-(3-methoxy-4-acetoxyphenyl)acrylic acid

[0046] 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.

[0047]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

[0049] (E)-3-(4-fluorophenyl)acrylic acid

[0050] 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 cinnamide derivate and an application as neuroprotective agent in pharmacy, wherein the derivate is represented as a formula (I), which has neuron protective activity and can be used to prepare anti-stroke drug.

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 neuroprotective agent. Background technique [0002] It has been reported in the literature that cinnamic acid derivatives have a certain protective effect on neurons. According to literature reports, benzhydryl piperazine compounds have good antioxidant activity. However, there is no disclosure of the condensation of substituted cinnamic acid derivatives and benzhydrylpiperazine compounds to form substituted cinnamic amide derivatives, and there is no report on whether these substituted cinnamic acid amide derivatives have neuron protection and cerebral apoplexy therapeutic activity . Contents of the invention [0003] One of the technical problems to be solved in the present invention is to disclose a new substituted cinnamic amide derivative with medical value. [0004] The second technical problem to be ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/185A61K31/495A61P9/10
Inventor 吴斌朱东亚李飞
Owner NANJING MEDICAL UNIV