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Aminoacetophenone thiosemicarbazone derivative and application thereof

A technology of aminoacetophenone thiosemicarbazide and derivatives, which is applied in the fields of cosmetics, medicines, food chemistry and agricultural pesticides, can solve the problems of insufficient safety and poor activity, and achieves simple preparation and strong inhibitory activity. , the effect of novel structure

Active Publication Date: 2015-02-04
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, most compounds or extracts cannot be used in production and life due to poor activity or insufficient safety. Finding low-toxicity and high-efficiency tyrosinase inhibitors is still an important research direction in this field

Method used

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  • Aminoacetophenone thiosemicarbazone derivative and application thereof
  • Aminoacetophenone thiosemicarbazone derivative and application thereof
  • Aminoacetophenone thiosemicarbazone derivative and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of 4'-acetamidoacetophenone thiosemicarbazone (compound 1):

[0025] Step 1, 4-aminoacetophenone obtains amidated acetophenone through carboxylic acid amidation reaction (this step is prior art): add p-aminoacetophenone (0.02mol), carboxylic acid (0.08 mol) and 1-2 grains of zeolite, the solution was heated slowly to keep the reactants slightly boiling for about 15 minutes. Then gradually increase the temperature to 100-105°C for about 45 minutes. When the thermometer reading drops, stop heating. Under constant stirring, the reactant was slowly poured into a beaker filled with 100ml of cold water while hot, continued to stir, fully cooled, and the amidated acetophenone crude product was separated out. Suction filter and wash the crude product with 5-10ml of cold water. Then washed 3 times with 20 mL of hot water, dried and recrystallized with a small amount of ethanol to obtain the product amidated acetophenone.

[0026] Step 2, the amida...

Embodiment 2

[0027] Embodiment 2: the synthesis of 4'-trifluoroacetamidoacetophenone thiosemicarbazone (compound 2)

[0028] Referring to Example 1 for the synthetic method, the obtained target product (compound 2) was a colorless solid with a yield of 92%. 1 H NMR (300MHz, DMSO-d 6 ):δ11.37(s,1H),10.26(s,1H),8.33(s,1H),8.02(d,J=8.7Hz,3H),7.72(d,J=8.7Hz,2H),2.31 (s,3H). 13 C NMR (75MHz, DMSO-d 6 ): δ178.8, 154.7, 154.2, 146.9, 137.1, 134.6, 127.3, 120.4, 13.7. ESI-MS (m / z) 305.1 [M+1] + .

Embodiment 3

[0029] Embodiment 3: the synthesis of 4'-trichloroacetamidoacetophenone thiosemicarbazone (compound 3)

[0030] Referring to Example 1 for the synthetic method, the obtained target product (compound 3) was a light yellow solid with a yield of 80%. 1 H NMR (300MHz, DMSO-d 6 ):δ10.95(s,1H),10.23(s,1H),8.30(s,1H),8.00(d,J=8.8Hz,3H),7.70(d,J=8.8Hz,2H),2.29 (s,3H). 13 C NMR (75MHz, DMSO-d 6 ): δ178.8, 159.6, 147.0, 138.0, 134.3, 127.2, 120.6, 92.9, 13.7. ESI-MS (m / z) 353.2 [M+1] + .

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Abstract

The invention discloses an aminoacetophenone thiosemicarbazone derivative shown as a formula I and application thereof. In the formula I, an amino group connected with R is at 3 position or 4 position of the phenyl ring, and R is selected from C1-C6 alky or halogenated alkyl or alkoxy, aryl or substituted aryl. The related compounds are novel in structure and simple to prepare, are strong in inhibition activity on tyrosinase and have extremely obvious application prospect.

Description

Technical field: [0001] The invention relates to the fields of cosmetics, medicines, food chemistry and agricultural pesticides, in particular to an aminoacetophenone thiosemicarbazone derivative and its application. Background technique: [0002] Tyrosinase, also known as phenol oxidase and polyphenol oxidase, is a multifunctional copper-containing enzyme that widely exists in microorganisms, animals, plants and the human body. This enzyme utilizes molecular oxygen to catalyze the oxidation of monophenols to diphenols (monophenolase activity) followed by the catalytic oxidation of diphenols to the corresponding quinones. The quinone undergoes a series of enzyme-catalyzed or non-enzyme-catalyzed processes to obtain mixed melanin. [0003] Tyrosinase is related to many biological processes, such as human aging and human pigmentation diseases. Recent studies have shown that the high expression of tyrosinase leads to a large amount of melanin, which is also closely related to...

Claims

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Application Information

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IPC IPC(8): C07C337/08A61Q19/02A61P35/00A61P25/16A01P7/04A23L3/3535
Inventor 宋森川游遨周杰朱国勋潘文龙宋化灿
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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