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

(Thiosemicarbazideformyl) phenoxyacetic acid derivative and application thereof

A technology of phenoxyacetic acid derivatives and thiosemicarbazide formal, which is applied in the fields of cosmetics, food, and medicinal chemistry, can solve the problems of low inhibitory activity, carcinogenicity, and high price, and achieve good tyrosinase inhibitory activity

Inactive Publication Date: 2012-12-19
SUN YAT SEN UNIV
View PDF5 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the types of tyrosinase inhibitors commonly used in the market are very limited, mainly including arbutin, kojic acid, vitamin C and its derivatives, etc. Arbutin is safe, but its inhibitory activity is low and the price is high. Vitamin C The price is low, the safety is good, and the activity is too poor to be used in large quantities, while the activity of kojic acid is better, but it is gradually discontinued due to its carcinogenic effect

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
  • (Thiosemicarbazideformyl) phenoxyacetic acid derivative and application thereof
  • (Thiosemicarbazideformyl) phenoxyacetic acid derivative and application thereof
  • (Thiosemicarbazideformyl) phenoxyacetic acid derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of methyl 4-(thiosemicarbazide formal) phenoxyacetate (compound 1)

[0032] Dissolve 2.44g (20mmol) of p-hydroxybenzaldehyde in 40mL dry acetone, add 5.52g (40mmol) of potassium carbonate (microwave activation) and 3.24g (30mmol) of methyl chloroacetate, and stir for 8 hours under reflux conditions after addition. TLC tracks until the reaction is complete. Filter and spin dry the solvent to obtain the initial product. The intermediate was separated by silica gel column chromatography with a yield of 83%.

[0033] Dissolve 5 mmol of the intermediate obtained above in anhydrous methanol, add 5 mmol of thiosemicarbazide, and stir for 4 hours under reflux conditions. TLC will track until the reaction is complete. After the reaction solution is cooled, it is filtered to obtain a white solid product, namely methyl 4-(thiosemicarbazide formal) phenoxyacetate (1), with a yield of 92%. 1 H-NMR(300MHz,DMSO-d 6 ): δ11.37(s,1H,NH), 8.16(s,1H,NH 2 ),8.01(s,1H,NCH...

Embodiment 2

[0082] Example 2 In vitro tyrosinase inhibitory activity test of (thiosemicarbazide formal) phenoxyacetic acid derivatives

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 (thiosemicarbazideformyl) phenoxyacetic acid derivatives and application of using the (thiosemicarbazideformyl) phenoxyacetic acid derivatives as tyrosinase inhibitors. The general formula of the (thiosemicarbazideformyl) phenoxyacetic acid derivatives is shown as formula I, wherein R<1> is selected from hydrogen or alkoxy with one to six carbon; and R<2> is selected from groups shown as the accompanying drawing and the R<3> is selected from linear alkyl with one to six carbon.

Description

Technical field [0001] The invention relates to the fields of cosmetics, food, and pharmaceutical chemistry, in particular to (thiosemicarbazide formal) phenoxyacetic acid derivatives and their application as tyrosinase inhibitors. technical background [0002] At present, tyrosinase (EC 1.14.18.1, Tyrosinase), also known as phenol oxidase, polyphenol oxidase, and catechol oxidase, is a multi-subunit copper-containing oxidoreductase with a complex structure. It is widely present in microorganisms and animals. In plants and humans. Tyrosinase has a unique dual catalytic function and is a key enzyme for the synthesis of melanin in organisms. It is closely related to human aging and human pigmentation diseases. Therefore, tyrosinase inhibitors can be used to treat common melanosis skin diseases such as freckles, chloasma, and age spots. At present, the whitening agents added in whitening cosmetics on the market are all tyrosinase inhibitors. , Such as arbutin, vitamin C derivative...

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): C07C337/08A61K31/216A61P35/00A61P17/00A61P25/16A61K8/46A61Q19/02A01N47/34A01P7/04A23L3/3535
Inventor 陈智勇牟德海宋化灿潘文龙万一千
Owner SUN YAT SEN UNIV
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