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Preparation method and application of 4-methoxy-cinnamaldehyde thiosemicarbazone

A kind of technology of cinnamaldehyde thiosemicarbazide and methoxymeat, which is applied in the field of preparation and application of 4-methoxycinnamaldehyde thiosemicarbazone, and can solve problems such as application that has not yet been reported.

Inactive Publication Date: 2010-04-21
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the application of this compound as an inhibitor of a new type of insecticide target protein, phenol oxidase, has not been reported yet.

Method used

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  • Preparation method and application of 4-methoxy-cinnamaldehyde thiosemicarbazone
  • Preparation method and application of 4-methoxy-cinnamaldehyde thiosemicarbazone
  • Preparation method and application of 4-methoxy-cinnamaldehyde thiosemicarbazone

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Experimental program
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Embodiment Construction

[0037] The synthetic steps of 1.4-methoxycinnamaldehyde thiosemicarbazone

[0038] Weigh 0.455g (5mmol) of thiosemicarbazide, dissolve in 10mL 95% ethanol solution, add 95% ethanol solution containing 0.81g 4-methoxycinnamaldehyde, under magnetic stirring, add 2mL glacial acetic acid, heat to reflux, thin The reaction progress was monitored by layer chromatography. After heating to reflux for 3 h, the reaction system was cooled to room temperature, left to crystallize at 4° C., and suction filtered to obtain a crude product.

[0039] The product was recrystallized by 50% ethanol, dried in an oven, weighed, and the calculated yield was 77.1%. Adopt mass spectrometry, infrared spectrum and nuclear magnetic resonance spectrum to identify the structure of the product obtained, the infrared spectrogram of 4-methoxycinnamaldehyde thiosemicarbazone see figure 1 , the ESI-MS mass spectrum of 4-methoxycinnamaldehyde thiosemicarbazone see figure 2 , The H NMR spectrum of 4-methoxycin...

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Abstract

The invention discloses a preparation method and application of 4-methoxy-cinnamaldehyde thiosemicarbazone, relates to a thiosemicarbazone compound and provides a compound, i.e. 4-methoxy-cinnamaldehyde thiosemicarbazone as well as a preparation method and application thereof in protein phenol oxidase of insecticide targets. The molecular formula of the 4-methoxy-cinnamaldehyde thiosemicarbazone is C11H13N3OS. The preparation method comprises the following steps: weighing and dissolving thiosemicarbazone in a solvent, adding 4-methoxy-cinnamaldehyde with same quality as thiosemicarbazone, stirring under the action of magnetic forace, adding a proper amount of glacial acetic acid, heating, reflux reacting, and then cooling a reaction system to the room temperature, standing for crystallizing, and filtering to obtain a crude product; and recrystallizing the crude product to obtain a product, i.e. the 4-methoxy-cinnamaldehyde thiosemicarbazone. The 4-methoxy-cinnamaldehyde thiosemicarbazone can be applied to the protein phenol oxidase of insecticide targets.

Description

technical field [0001] The invention relates to a thiosemicarbazone compound, in particular to the preparation and application of a 4-methoxycinnamaldehyde thiosemicarbazone. Background technique [0002] Thiosemicarbazone compounds are Schiff base compounds formed by the condensation of thiosemicarbazides and corresponding aldehydes or ketones, which have a wide range of biological activities and have attracted much attention in the fields of medicine and chemistry. Li Jinzhou ([1] Li Jinzhou, Zhang Guanglin, Sha Jingquan, et al. Synthesis, spectral characterization and biological activity of furoylpyrazolone thiosemicarbazone complexes[J]. Spectroscopy and Spectral Analysis, 2005, 25(2): 216-219) found that furoyl pyrazolone thiosemicarbazone has good antibacterial effect on Staphylococcus aureus, Bacillus subtilis, Escherichia coli, soft rot of cabbage and Phytophthora solani ; Richardson ([2]RichardsonD R.Therapeutic potential of iron chelators in cancer therapy[J].Adv....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C337/08A01N47/34A01P7/04
Inventor 陈清西李智聪马素娟朱育菁
Owner XIAMEN UNIV