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Homopiperony lamine 3-methyl-5-chlorine salicylide and synthesis method and application thereof

A technology of piperonyl ethylamine and chlorosalicylaldehyde, which is applied in the field of medicine, can solve problems such as new Schiff bases that have not yet been seen, and achieve good medicinal value, mild reaction conditions, and simple synthesis methods

Inactive Publication Date: 2014-05-28
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no relevant reports on the synthesis and activity research of novel Schiff bases based on piperonylethylamine and 3-methyl-5-chlorosalicylaldehyde.

Method used

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  • Homopiperony lamine 3-methyl-5-chlorine salicylide and synthesis method and application thereof
  • Homopiperony lamine 3-methyl-5-chlorine salicylide and synthesis method and application thereof
  • Homopiperony lamine 3-methyl-5-chlorine salicylide and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Dissolve 0.01mol of 3-methyl-5-chlorosalicylaldehyde and 0.01mol of piperonylethylamine in 30mL of absolute ethanol (use Molecular sieve dehydration), the obtained solution was refluxed and reacted at 78°C under stirring conditions until complete (TLC tracking detection, about 4h), after the reaction was stopped, the reaction solution was fully cooled to 20°C, and stood for 6h, yellow needle-shaped crystals were precipitated, filtered , the obtained crystals were vacuum-dried at 30° C. for 1 h to obtain a yellow solid product with a yield of 90%.

[0025] The yellow solid product obtained above was subjected to infrared spectrum, ultraviolet spectrum, 1 H and 13 C nuclear magnetic resonance spectrum and electrospray mass spectrometry identification, their spectra are as follows figure 1 , 2 , 3, 4 and 5, the specific spectral characteristics are as follows:

[0026] Infrared spectrum: (KBr,cm -1 )3440(ν N-H ),2918(ν Ar-H ),1635(ν C=N ), 1503, 1440 (ν C=C ), 12...

Embodiment 2

[0034] Get 0.01mol of 3-methyl-5-chloro salicylaldehyde and 0.01mol of piperonyl ethylamine and dissolve in 120mL of dichloromethane (dichloromethane is used Molecular sieve dehydration), the resulting solution was stirred and reacted at 45°C until complete (TLC tracking detection, about 6h), after the reaction was stopped, most of the methylene chloride (accounting for 80% of the amount of methylene chloride) was removed by distillation under reduced pressure, and the remaining The reaction solution was fully cooled to 10°C and left to stand for 2 hours. Yellow needle-like crystals were precipitated and filtered. The obtained crystals were vacuum-dried at room temperature for 12 hours to obtain a yellow solid product with a yield of 70%.

[0035] The above-mentioned yellow solid product is subjected to spectroscopic analysis, and its spectral characteristics are the same as the product obtained in Example 1. Therefore, it can be determined that the yellow solid product obtain...

Embodiment 3

[0037] Take 0.01mol of 3-methyl-5-chlorosalicylaldehyde and 0.01mol of piperonyl ethylamine and dissolve in 300mL of chloroform / anhydrous methanol mixed solvent (the volume ratio of chloroform and anhydrous methanol is 2:1, chloroform and Anhydrous methanol before use Molecular sieve dehydration), the obtained solution was refluxed and stirred at 65°C until the reaction was complete (TLC tracking detection, about 1h). The solution was fully cooled to 15°C, left standing for 12h, and yellow needle-like crystals were precipitated, filtered, and the obtained crystals were vacuum-dried at 35°C for 6h to obtain piperonyl ethylamine 3-methyl-5-chlorosalicylaldehyde with a yield of 72%. .

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Abstract

The invention discloses a homopiperony lamine 3-methyl-5-chlorine salicylide and synthesis method and application of the homopiperony lamine 3-methyl-5-chlorine salicylide. The synthesis method of the homopiperony lamine 3-methyl-5-chlorine salicylide comprises the following steps: weighing the same amount of substance of 3-methyl-5-chlorine salicylide and homopiperony lamine and enabling the 3-methyl-5-chlorine salicylide and the homopiperony lamine to be dissolved in an organic solvent, carrying out a condensation reaction of the 3-methyl-5-chlorine salicylide, the homopiperony lamine and the organic solvent at a temperature in a range from 45 DEG C to the boiling temperature of the solvent, reacting completely and then cooling, standing for crystallization, separating crystal and drying to obtain the homopiperony lamine 3-methyl-5-chlorine salicylide. Proliferation inhibitory activity to eight kinds of human malignant tumor cell strains of the homopiperony lamine 3-methyl-5-chlorine salicylide are tested, the results show that the homopiperony lamine 3-methyl-5-chlorine salicylide has the highest toxicity selectivity on human hepatoma cellHepG2, and inhibitory activity of cisplatin drug-resistant strain to ovarian cancer is higher than cisplatin. The homopiperony lamine 3-methyl-5-chlorine salicylide has the value of deep study and development, and the constitutional formula of the homopiperony lamine 3-methyl-5-chlorine salicylide is shown in the description.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to piperonyl ethylamine 3-methyl-5-chlorosalicylaldehyde and its synthesis method and application. Background technique [0002] Schiff bases are a very important class of organic compounds, which are characterized by imine or imine characteristic groups (-RC=N-), which are usually formed by condensation of amines and active carbonyl groups. The functions and applications of Schiff bases are very extensive, including medicine, biology, materials and many other fields, among which it is one of the hot research fields in pharmaceutical research. [0003] Existing research results have fully demonstrated that Schiff bases have a wide range of biological and pharmacological activities, such as antitumor, antibacterial, antiviral, antimalarial, anti-inflammatory and antipyretic. The unique imine group or imine group of Schiff base is quite common in nature, derivatives and synthetic co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/58A61K31/36A61P35/00
Inventor 陈振锋梁宏刘延成彭艳杨扬陈思园
Owner GUANGXI NORMAL UNIV
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