Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Pyrazoline derivative and application of pyrazoline derivative as tyrosinase inhibitor

A technology of pyrazoline and derivatives, which is applied in the direction of drug combinations, medical preparations containing active ingredients, organic active ingredients, etc., to achieve the effect of good application prospects

Inactive Publication Date: 2015-10-07
WUHAN UNIV OF TECH
View PDF0 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the mechanism of tyrosinase inhibition at home and abroad.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Pyrazoline derivative and application of pyrazoline derivative as tyrosinase inhibitor
  • Pyrazoline derivative and application of pyrazoline derivative as tyrosinase inhibitor
  • Pyrazoline derivative and application of pyrazoline derivative as tyrosinase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Compound 1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-3-(4-dimethylamino-naphthalen-1-yl)-propenone ( 4) Synthesis of:

[0042] 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone (1.78 g, 10 mml) was added to 4-dimethylamino-1-naphthalene Aldehyde (1.99g, 10mml) in ethanol solution (15ml). 50% NaOH solution was added dropwise to the reaction mixture to make it alkaline (PH=10), and the reaction mixture was stirred at 27°C for 8 hours. TLC monitored the completion of the reaction. The reaction solution was poured into 50 ml of hydrochloric acid ice-water mixture (1 ml of concentrated hydrochloric acid). Extracted with ethyl acetate (50ml), washed with water (150ml), dried over anhydrous magnesium sulfate, concentrated in a rotary evaporator to obtain light yellow powder 1-(2,3-dihydro-benzo[1,4]diox Heterocyclohexen-6-yl)-3-(4-dimethylamino-naphthalen-1-yl)-propenone (4) 1.76 g, yield 49%.

[0043] 1 H NMR (500MHz, CDCl 3 )δ: 7.78(d, J=8.5Hz, H), 7.66(d, J=7.0Hz, H), 7.56(d...

Embodiment 2

[0044] Example 2. Compound 3-benzofuran-2-yl-5-(4-dimethylamino-naphthalene-1-yl)-4,5-dihydro-pyrazole-1-thioformic acid amide (1a )Synthesis:

[0045] 2-Acetylbenzofuran (1.60 g, 10 mml) was added to a solution (15 ml) of 4-dimethylamine-1-naphthaldehyde (1.99 g, 10 mml) in ethanol. 50% NaOH solution was added dropwise to the reaction mixture to make it alkaline (PH=10), and the reaction mixture was stirred at 27°C for 8 hours. TLC monitored the completion of the reaction. The reaction solution was poured into 50 ml of hydrochloric acid ice-water mixture (1 ml of concentrated hydrochloric acid). It was extracted with ethyl acetate (50ml), washed with water (150ml), dried over anhydrous magnesium sulfate, and concentrated by a rotary evaporator to obtain 1.70g of chalcone (1) with a yield of 50%.

[0046] Thiosemicarbazide (0.55 g, 6 mmol) was added to a solution of chalcone (1) (1.70 g, 5 mmol) in ethanol (15 ml). 50% NaOH solution was added dropwise to the reaction mixtu...

Embodiment 3

[0048] Example 3. Compound 3-benzofuran-2-yl-5-(4,7-dimethoxynaphthalene-1-yl)-4,5-dihydro-pyrazole-1-thioformic acid amide ( Synthesis of 2a):

[0049] Using 4,6-dimethoxy-1-naphthylaldehyde instead of 4-dimethylamine-1-naphthaldehyde, the others were the same as in Example 2 to obtain white powder pyrazoline (2a) with a yield of 39%.

[0050] 1 H NMR (500MHz, CDCl 3 )δ:8.87(s,D 2 O exchangeable, 2H, NH 2 ),7.89-7.29(m,J=8.0Hz, 8H),7.16(s,1H),6.92(d,J=8.0Hz,1H),5.57-5.50(dd,J=11.5Hz,1H),4.22 -4.19(dd, J=11.5Hz, 1H), 3.85(s, 6H), 3.47-3.34(dd, J=17.5Hz, 1H); Mass Spectrum(ESI) m / z: 432.52[M+H]+ ;Microanalysis Calculated for C 24 h 21 N 3 o 3 S(431.51), C, 66.80%; H, 4.91%; N, 9.74%; S, 7.43%. Found C: 66.97%, H: 4.98%, N: 9.73%, S: 7.41%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a series of pyrazoline derivatives. Claisen-schmidt condensation reaction is carried out on equivalent molar weights of ketone and aldehyde under alkaline condition, so that chalcone is synthesized; reaction is carried out on chalcone and thiosemicarbazide under the alkaline condition, so that the pyrazoline derivative is obtained; and the same reaction is carried out on chalcone and N-(4-chlorophenyl) semicarbazide under the alkaline condition, so that the pyrazoline derivative is synthesized. Biological activity determination on the series of compounds proves that the synthesized pyrazoline derivative has tyrosinase inhibitory effect and anti-tumour biological activity, is applicable to being taken as a tyrosinase inhibitor and a medicine used for preventing or treating a tumour disease and has a good potential application prospect.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, and in particular relates to a pyrazoline derivative and its application. Background technique [0002] Tyrosinase is a key enzyme for the synthesis of melanin in organisms. It is related to pigment disorders and abnormal pigment deposition, and is also the main factor causing enzymatic browning of fruits and vegetables, and it also affects the immunity and growth of insects. Because of its wide existence, it has a good application prospect in medical treatment, whitening, preservation and insecticide. Tyrosinase has the activity of monophenolase and bisphenolase, and monophenolase has the characteristics of hysteresis effect in the catalytic process, and the enzyme concentration, substrate and effector will all affect the length of the hysteresis time. [0003] Tyrosinase is a multi-subunit copper-containing oxidoreductase with a complex structure. It first hydroxylates tyrosine to produce or...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D405/04C07D319/18A61K31/4155A61K31/357A61P35/00
CPCC07D319/18C07D405/04
Inventor 秦华利尚振鹏陈小清郝建宏冷静王晓燕
Owner WUHAN UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com