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Acylhydrazone compound and preparation method and application thereof

A compound and lead compound technology, applied in organic chemistry, drug combination, pharmaceutical formulation, etc., can solve problems such as damage and unsatisfactory curative effect

Active Publication Date: 2019-03-08
SHENYANG SUNSHINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Current research shows that the neurons of patients with brain injury and some neurodegenerative diseases such as Alzheimer's disease and Parkinson's syndrome have damage and atrophy, and the current drugs for the treatment of these diseases are not very effective

Method used

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  • Acylhydrazone compound and preparation method and application thereof
  • Acylhydrazone compound and preparation method and application thereof
  • Acylhydrazone compound and preparation method and application thereof

Examples

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preparation example Construction

[0040] The preparation method of the above-mentioned acylhydrazone compounds includes steps S110-S130.

[0041] The synthetic route of above-mentioned acylhydrazone compound is:

[0042]

[0043] The specific steps S110-S130 are as follows:

[0044] S110. Carrying out hydrazine hydrolysis reaction of compound A and 80% hydrazine hydrate by mass percentage to obtain compound B, wherein the structure of compound A is: The structural formula of compound B is:

[0045] Specifically, compound A was prepared using isoniazid. The specific steps for preparing compound A include the operations of S111-S115.

[0046] S111. Compound D is prepared.

[0047] Isoniazid and CS 2 Nucleophilic addition reaction in KOH affords compound D. The reaction formula for preparing compound D is as follows:

[0048]

[0049] Specifically, first dissolve the KOH solid in absolute ethanol to obtain a potassium hydroxide ethanol solution, and then add isoniazid to the potassium hydroxide et...

Embodiment 1

[0079] (1) Synthesis of Compound C

[0080] The first step: the synthetic route of compound D is as follows:

[0081]

[0082] Mix 7.8016g (0.1390mol) of KOH solid with 150ml of absolute ethanol, heat and stir until it dissolves, and after the solution is cooled to room temperature, add 10.0380g (0.0732mol) of isoniazid to it, and slowly add 6mL of CS 2 , magnetically stirred at room temperature for 10 h to produce a yellow solid, which was then suction filtered and dried in vacuo to obtain Compound D as a yellow powder. Yield: 19.4775 g, crude yield: 105.9%.

[0083] The second step: the synthetic route of compound C is as follows:

[0084]

[0085] 12.9884g (0.0517mol) of compound D obtained in the first step and 20mL (0.41mol) of 80% hydrazine hydrate in mass percentage were mixed with 20mL of ice water after magnetic stirring and reflux in an oil bath at 143°C for 4 hours, and then Adjust the pH to 5 with concentrated hydrochloric acid to produce a white solid, th...

Embodiment 2

[0103] (1) Synthesize Compound B according to the steps of Synthesis Compound B in Example 1.

[0104] (2) Dissolve 0.2085 g (0.78 mmol) of compound B in 70 mL of anhydrous methanol to obtain a pre-reaction solution. Then, 0.18 mL (1.43 mmol) of cinnamaldehyde was added to the pre-reaction solution, and heated to reflux at 67° C. for 4 h. Stand to cool and crystallize, filter with suction, and recrystallize from absolute ethanol to obtain 0.2982g of white crystals, which have the structural formula: acylhydrazone compounds. The yield was 38.1%. MS (ESI) m / z: 380.

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Abstract

The invention relates to an acylhydrazone compound and a preparation method and the application thereof. The acylhydrazone compound has the following structure as shown in a formula, wherein, R is selected from one of the two parts of the formula. The acylhydrazone compound can promote neural cell differentiation and neurite growth.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an acylhydrazone compound and its preparation method and application. Background technique [0002] The maturation process of neurons goes through neurite outgrowth, extension, axonal, dendritic differentiation decisions, and neurite formation. These developmental processes are precisely regulated to form a highly complex neural network that influences our learning, memory and emotional activity. Current studies have shown that neurite damage and atrophy exist in patients with brain injury and some neurodegenerative diseases such as Alzheimer's disease and Parkinson's syndrome, and the current drugs for treating these diseases are not very effective. Therefore, the development of compounds that can promote neural differentiation or neurite growth is of great significance to the development of drugs for the treatment of brain injury and neurodegenerative diseases. Con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D409/14C07D401/14A61K31/4439A61K31/444A61P25/00
CPCA61P25/00C07D401/04C07D401/14C07D409/14
Inventor 林红卫向小亮蒋霞刘益林
Owner SHENYANG SUNSHINE PHARMA
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