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A kind of pyridine acylhydrazone compound, synthesis method and application

A technology of pyridine acyl hydrazone and synthesis method, applied in the field of medicinal chemistry, can solve the problems of low yield of pyridine acyl hydrazone, complicated synthesis process and the like

Active Publication Date: 2020-07-28
XIAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the synthetic methods of existing pyridine acylhydrazones, the yield is low and the synthetic process is complicated.

Method used

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  • A kind of pyridine acylhydrazone compound, synthesis method and application
  • A kind of pyridine acylhydrazone compound, synthesis method and application
  • A kind of pyridine acylhydrazone compound, synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: a kind of pyridine acylhydrazone compound, its reaction formula and structural formula are:

[0044]

[0045] Structure 1 is p-chlorobenzaldehyde-4-chloropyridine-2-formylhydrazone with molecular formula C 13 h 9 Cl 2 N 3 O, the specific preparation method is:

[0046] 1) Preparation of 4-chloropyridine-2-carboxyl hydrazide;

[0047] 2) Dissolve 0.0686g (0.4mmol) of 4-chloropyridine-2-carboxylhydrazide in 10.0mL of methanol to obtain solution 1;

[0048] 3) Weigh 0.0562g (0.4mmol) p-chlorobenzaldehyde and dissolve it in 5mL glacial acetic acid, and obtain solution 2 after completely dissolving;

[0049] 4) Slowly add solution 2 to solution 1. After stirring at 60°C and refluxing in a water bath for 4 hours, the solution is colorless and transparent. Filter it while it is hot. After standing for one day at room temperature, a large number of white rod-shaped crystals p-chlorobenzaldehyde- 4-Chloropyridine-2-formylhydrazone (yield 56%, melting range...

Embodiment 2

[0050] Embodiment 2: a kind of pyridine acylhydrazone compound, its reaction formula and structural formula are:

[0051]

[0052] Structure II is p-bromobenzaldehyde-4-chloropyridine-2-formylhydrazone, and the molecular formula is C 13 h 9 BrClN 3 O, the specific preparation method is:

[0053] 1) Preparation of 4-chloropyridine-2-carboxyl hydrazide;

[0054] 2) Dissolve 0.0343g (0.2mmol) 4-chloropyridine-2-carboxylhydrazide in 10.0mL ethanol to obtain solution 1;

[0055] 3) Weigh 0.0370g (0.2mmol) p-bromobenzaldehyde and dissolve it in 5mL ethanol, and obtain solution 2 after completely dissolving;

[0056] 4) Slowly add solution 2 to solution 1. After stirring at 80°C and refluxing in a water bath for 4 hours, the solution is colorless and transparent. Filter it while it is hot. After standing for two days at room temperature, a large number of white rod-shaped crystals p-bromobenzaldehyde- 4-Chloropyridine-2-formylhydrazone (62% yield, melting range 247.23-247.78°C)...

Embodiment 3

[0058] Embodiment 3: a kind of pyridine acylhydrazone compound, its reaction formula and structural formula are:

[0059]

[0060] Structure III is p-iodobenzaldehyde-4-chloropyridine-2-formylhydrazone, the molecular formula is C 13 h 9 ClIN 3 O, the specific preparation method is:

[0061] 1) Preparation of 4-chloropyridine-2-carboxyl hydrazide;

[0062] 2) Dissolve 0.0686g (0.4mmol) of 4-chloropyridine-2-carboxylhydrazide in 10.0mL of methanol to obtain solution 1;

[0063] 3) Weigh 0.0928g (0.4mmol) p-iodobenzaldehyde and dissolve it in 5.0mL glacial acetic acid, and obtain solution 2 after completely dissolving;

[0064] 4) Slowly add solution 2 to solution 1. After stirring at 80°C and refluxing in a water bath for 4 hours, the solution is colorless and transparent. Filter it while it is hot. After standing for one day at room temperature, a large number of white rod-shaped crystals of p-iodobenzaldehyde- 4-Chloropyridine-2-formylhydrazone (79% yield, melting rang...

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Abstract

The invention relates to a pyridine acylhydrazone compound as well as a synthetic method and application thereof. The structure of the compound is formula (shown in the description), wherein R represents halogen. The invention provides the pyridine acylhydrazone compound with a novel synthetic structure, the structure of the synthesized acylhydrazone compound contains pyridine rings and halogen atoms, and the biological activity of the compound can be improved by N heterocyclic rings and halogen.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a pyridine acylhydrazone compound, a preparation method thereof, and an application of the compound. Background technique [0002] As an important Schiff base compound, acylhydrazone has attracted widespread attention from scientists due to its special acylhydrazone group (CONHN=CR), which endows acylhydrazone compounds with better biological activity. , novel physical and chemical properties and its wide application value. [0003] Pyridine acylhydrazone ligands containing N heterocycles generally have good biological activity, strong coordination ability and various coordination modes. In recent years, many documents have reported the superior biological activity of pyridine acylhydrazones and their complexes and their wide application in other fields, and the research on these compounds has attracted much attention. According to consulting, the yield of the exist...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/88A61P31/04
CPCA61P31/04C07B2200/13C07D213/88Y02A50/30
Inventor 刘向荣廖庚晖杨杰宗新杰赵顺省杨再文杨征杨水兰
Owner XIAN UNIV OF SCI & TECH