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Uses of aminosalicylic acid derivative as neuroprotective agent

A technology of aminosalicylic acid and derivatives, applied in the field of aminosalicylic acid derivatives and neuroprotective agents, to achieve strong cell damage, good neuroprotective effect, and good therapeutic activity for stroke

Inactive Publication Date: 2009-07-29
NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since NMDA receptors and nNOS have many important physiological functions, although inhibiting the function of NMDA receptors and nNOS can prevent the pathological release of NO, it will also produce serious side effects

Method used

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  • Uses of aminosalicylic acid derivative as neuroprotective agent
  • Uses of aminosalicylic acid derivative as neuroprotective agent
  • Uses of aminosalicylic acid derivative as neuroprotective agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 15

[0026] Example 15-(5-chloro-2-hydroxybenzylamino)-2-hydroxybenzoic acid (JX-1)

[0027] Dissolve 1.57g (0.01mol) of 5-chloro-2-hydroxybenzaldehyde in 20ml of absolute ethanol, 1.53g (0.01mol) of 5-aminosalicylic acid in 40ml of absolute ethanol, 5ml of water and 1ml of concentrated hydrochloric acid In the mixed solvent, mix the two, reflux for 30 minutes, cool and precipitate the solid, filter, add 20ml of absolute ethanol to the filter cake, add 1.5g of sodium borohydride at 0-5°C, after the addition is complete, stir for 0.5 hours, and reflux for 30 minutes. Cool, adjust the pH to 1-2 with concentrated hydrochloric acid, filter, add 100ml of water, stir for 30 minutes, and filter to obtain the target compound.

Embodiment 25

[0028] Example 25-(5-bromo-2-hydroxybenzylamino)-2-hydroxybenzoic acid (JX-2)

[0029] Dissolve 2.01g (0.01mol) of 5-bromo-2-hydroxybenzaldehyde in 20ml of absolute ethanol, 1.53g (0.01mol) of 5-aminosalicylic acid in 40ml of absolute ethanol, 5ml of water and 1ml of concentrated hydrochloric acid In the mixed solvent, mix the two, reflux for 30 minutes, cool and precipitate the solid, filter, add 20ml of absolute ethanol to the filter cake, add 1.5g of sodium borohydride at 0-5°C, after the addition is complete, stir for 0.5 hours, and reflux for 30 minutes. Cool, adjust the pH to 1-2 with concentrated hydrochloric acid, filter, add 100ml of water, stir for 30 minutes, and filter to obtain the target compound.

[0030] 13 C-NMR (d-DMSO) δ: 40.34, 110.03, 111.79, 112.60, 111.96, 117.45, 122.00, 128.3, 129.70, 130.00, 140.51, 153.07, 154.35, 171.81

Embodiment 3

[0031] Example 3 5-(3,5-dichloro-2-hydroxybenzylamino)-2-hydroxybenzoic acid (JX-3)

[0032] Dissolve 1.91g (0.01mol) of 3,5-dichloro-2-hydroxybenzaldehyde in 20ml of absolute ethanol, 1.53g (0.01mol) of 5-aminosalicylic acid in 40ml of absolute ethanol, 5ml of water and 1ml In the mixed solvent of concentrated hydrochloric acid, mix the two, reflux for 30 minutes, cool and precipitate the solid, filter, add 20ml of absolute ethanol to the filter cake, add 1.5g of sodium borohydride at 0-5°C, complete the addition, stir for 0.5 hours, and reflux After cooling for 30 minutes, adjust the pH to 1-2 with concentrated hydrochloric acid, filter, add 100ml of water, stir for 30 minutes, and filter to obtain the target compound.

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Abstract

The invention relates to an aminosalicylic acid derivative. The structure of the aminosalicylic acid derivative accords with the following general formula (I). At least one of R1, R2, R3 and R5 is -OH; when R1, R2, R3 and R5 are not -OH, R1, R2, R3 and R5 are -H, -OCH3, -F, -Cl, -Br, -CF3 or -NO3; R4 is -OCH3, -F, -Cl, -Br, -CF3 or -NO3; R6 and R7 are -COOH or -OH. When R6 is -COOH, R7 is -OH; when R6 is -OH, R7 is -COOH. In the invention, target compounds have strong protection function on PC12 cell injuries caused by glutamate. And the target compounds block the coupling between PSD-95 and nNOS by specificity to develop the pharmacological action.

Description

1. Technical field [0001] The invention belongs to the field of pharmacy, and provides a derivative of aminosalicylic acid and the use of the derivative as a neuroprotective agent. 2. Background technology [0002] Prior Art: Neuroprotective agents are currently a research hotspot in the treatment of ischemic stroke. So far, hundreds of neuroprotective agents have been developed for different links of the cerebral infarction cascade reaction, but except for the free radical scavenger Edaravone, almost all neuroprotective agents are effective in animal experiments, clinically ineffective or The effect is very poor, or the clinical application is limited due to serious side effects. Seeking new neuroprotective agents has become the focus of current research. [0003] There are three main pathways for the death of neurons after cerebral ischemia injury: calcium influx caused by ischemia activates nitric oxide synthase (NOS), leading to pathological release of nitric oxide (NO...

Claims

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Application Information

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IPC IPC(8): C07C229/64A61K31/606A61P25/00A61P9/10
Inventor 朱东亚李飞季兴周丽吴斌
Owner NANJING MEDICAL UNIV
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