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Tyrosinase inhibitor, and preparation method and applications thereof

A compound and pharmaceutical technology, applied in the field of medicine, can solve problems such as restricted use and safety issues

Active Publication Date: 2018-12-04
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some safety concerns with these tyrosinase inhibitors limit their use

Method used

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  • Tyrosinase inhibitor, and preparation method and applications thereof
  • Tyrosinase inhibitor, and preparation method and applications thereof
  • Tyrosinase inhibitor, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (1) Synthesis of 1-(2,4-bis(benzyloxy)phenyl)ethanone

[0054] Take 2,4-dihydroxyacetophenone (5g, 32.8mmol) and benzyl bromide (14.1g, 82.2mmol), add it to an eggplant-shaped flask, add acetonitrile, heat in an oil bath at 85°C, and reflux the reaction solution for 3-5 Hours, after the reaction is over, spin off the acetonitrile and add water, extract with ethyl acetate, wash with brine, dry the organic layer, recrystallize, filter with suction, and dry the filter cake under infrared to obtain a white solid with a yield of 95%.

[0055] (2) Synthesis of ethyl 4-(2,4-bis(benzyloxy)phenyl)-2,4-dioxobutanoate

[0056] Take 1-(2,4-bis(benzyloxy)phenyl)ethanone (8g, 24.1mmol), diethyl oxalate (4.22g, 28.9mmol) and sodium ethoxide (3.28g, 48.1mmol), add to Add ethanol to an eggplant-shaped bottle, heat in an oil bath at 80°C, reflux the reaction solution for 5-8 hours, and cool to room temperature; a yellow solid precipitates, is suction filtered, and the filter cake is dri...

Embodiment 2

[0069] Preparation of 3-(2,4-dihydroxyphenyl)-N-(o-tolyl)-1H-pyrazole-5-carboxamide:

[0070] Referring to the synthesis method of Example 1, the intermediate 1 of Example 1 was replaced by 3-(2,4-bis(benzyloxy)phenyl)-N-(o-tolyl)-1H-pyrazole-5-methyl Amide, to obtain a white solid compound, which was detected as one point by TLC, with fluorescence at 254nm and no fluorescence at 365nm under a UV lamp.

[0071] 1 H NMR(300MHz,DMSO-d6)δ13.16(s,1H),10.18(s,1H),9.61(s,1H),9.39(s,1H),7.71(s,1H),7.48(d, J=8.3Hz, 1H), 7.24(m, 2H), 7.11(s, 1H), 7.01(s, 1H), 6.45(s, 1H), 6.34(d, J=8.3Hz, 1H), 2.28( s,3H).ESI-MS m / z 310.1211[M+H] + .

Embodiment 3

[0073] Preparation of 3-(2,4-dihydroxyphenyl)-N-(m-tolyl)-1H-pyrazole-5-carboxamide:

[0074] Referring to the synthesis method of Example 1, the intermediate 1 of Example 1 was replaced by 3-(2,4-bis(benzyloxy)phenyl)-N-(m-tolyl)-1H-pyrazole-5-methyl Amide, to obtain a white solid compound, which was detected as one point by TLC, with fluorescence at 254nm and no fluorescence at 365nm under a UV lamp.

[0075] 1 H NMR (300MHz, DMSO-d6) δ9.92(s, 2H), 7.69–7.55(m, 2H), 7.49(d, J=8.5Hz, 1H), 7.23(t, J=7.7Hz, 1H) ,7.14(s,1H),6.91(d,J=7.2Hz,1H),6.45(d,J=2.2Hz,1H),6.35(dd,J=8.5,2.3Hz,1H),2.31(s, 3H).ESI-MS m / z 310.1203[M+H] + .

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Abstract

The invention belongs to the field of medicine, relates to a tyrosinase inhibitor (I) and a preparation method thereof, and more specifically relates to 2, 4-dihydroxy phenol-pyrazol-aniline structurecompound. It is confirmed by pharmacodynamic tests that the 2, 4-dihydroxy phenol-pyrazol-aniline structure compound is capable of preventing melanin generation through inhibiting tyrosinase activity, and can be used for preparation of medicines used for preventing or treating melanin overexpression diseases.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a class of tyrosinase inhibitors and a preparation method thereof, in particular to 2,4-dihydroxyphenol-pyrazole-aniline structural compounds, which have anti-melanin production by inhibiting tyrosinase activity effect. Background technique [0002] Tyrosinase (Tyrosinase, EC.1.14.18.1) is a ketone-containing metalloenzyme, which has both monophenolase and diphenolase biological activities, and is widely distributed in animals, plants and microorganisms. It is often called tyrosinase in animals and microorganisms, and polyphenol oxidase in plants. Tyrosinase is a key enzyme in the process of melanin production. Directly inhibiting the catalytic activity of tyrosinase can prevent the synthesis of melanin. Therefore, inhibition of tyrosinase is promising for the treatment of diseases related to the overexpression of melanin, such as freckles and age spots. , melasma, post-inflammatory melan...

Claims

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Application Information

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IPC IPC(8): C07D231/14C07D405/12C07D401/12A61P17/00A61P35/00A61K31/415A61K31/4155A61K31/4439A61P43/00
CPCA61P17/00A61P35/00A61P43/00C07D231/14C07D401/12C07D405/12
Inventor 孙昊鹏莫俊陈瑶冯锋
Owner CHINA PHARM UNIV
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