72678-94-5

Basic information

• Product Name: 2-(3,4,5-TRIMETHOXYPHENYL)-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID
• Synonyms: 2-(3,4,5-TRIMETHOXY-PHENYL)-THIAZOLIDINE-4-CARBOXYLIC ACID;2-(3,4,5-TRIMETHOXYPHENYL)-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID;(4R)-2-(3,4,5-trimethoxyphenyl)-1,3-thiazolidine-4-carboxylic acid;(4R)-2-(3,4,5-trimethoxyphenyl)-4-thiazolidinecarboxylic acid;(4R)-2-(3,4,5-trimethoxyphenyl)thiazolidine-4-carboxylic acid;(4S)-2-(3,4,5-trimethoxyphenyl)thiazolidine-4-carboxylic acid
• CAS NO: 72678-94-5
• Molecular Formula: C₁₃H₁₇NO₅S
• Molecular Weight: 299.34
• Mol File: 72678-94-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 493.6 °C at 760 mmHg
• Flash Point: 252.3 °C
• Appearance: /
• Density: 1.286 g/cm³
• Vapor Pressure: 1.46E-10mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 2-(3,4,5-TRIMETHOXYPHENYL)-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4,5-TRIMETHOXYPHENYL)-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID(72678-94-5)
• EPA Substance Registry System: 2-(3,4,5-TRIMETHOXYPHENYL)-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID(72678-94-5)

Safety Data

• Hazardous Substances Data: 72678-94-5(Hazardous Substances Data)

Usage

Uses

2-(3,4,5-Trimethoxy-phenyl)-thiazolidine-4-carboxylic Acid is used in the preparation of phenylthiazolidinecarboxamides as platelet activating factor (PAF) inhibitors

InChI:InChI=1/C13H17NO5S/c1-17-9-4-7(5-10(18-2)11(9)19-3)12-14-8(6-20-12)13(15)16/h4-5,8,12,14H,6H2,1-3H3,(H,15,16)

Upstream product

• 52-90-4 L-Cysteine 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 1426937-84-9 C₁₈H₂₃NO₅S 
• 1426937-83-8 dimethyl (3R)-3-(3,4,5-trimethoxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 
• 69570-46-3 (R)-3-((S)-3-Mercapto-2-methyl-propionyl)-2-(3,4,5-trimethoxy-phenyl)-thiazolidine-4-carboxylic acid 
• 637032-09-8 2-(3,4,5-trimethoxy-phenyl)-thiazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 
• 72678-41-2 (R)-3-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-2-(3,4,5-trimethoxy-phenyl)-thiazolidine-4-carboxylic acid 

Relevant articles and documents

NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR

Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

Design, synthesis and biological evaluation of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors

Herein we describe the design, synthesis and biological activities of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors. The target compounds 2a-2j were designed and synthesized from the structural characteristics of N-phenylthiourea, tyrosinase inhibitor and tyrosine, and l-DOPA, the natural substrates of tyrosinase. Among them, (2R/S,4R)-2-(2,4-dimethoxyphenyl)thiazolidine-4-carboxylic acid (2g) caused the greatest inhibition 66.47% at 20 μM of l-DOPA oxidase activity of mushroom tyrosinase. Kinetic analysis of tyrosinase inhibition revealed that 2g is a competitive inhibitor. We predicted the tertiary structure of tyrosinase, and simulated the docking of mushroom tyrosinase with 2g. These results suggest that the binding affinity of 2g with tyrosinase is high. Also, 2g effectively inhibited tyrosinase activity and reduced melanin levels in B16 cells treated with α-MSH. These data strongly suggest that 2g can suppress the production of melanin via the inhibition of tyrosinase activity.

Discovery of 4-substituted methoxybenzoyl-aryl-thiazole as novel anticancer agents: Synthesis, biological evaluation, and structure-activity relationships

A series of 4-substituted methoxybenzoyl-aryl-thiazoles (SMART) have been discovered and synthesized as a result of structural modifications of the lead compound 2-arylthiazolidine-4-carboxylic acid amides (ATCAA). The antiproliferative activity of the SMART agents against melanoma and prostate cancer cells was improved from μM to low nM range compared with the ATCAA series. The structure-activity relationship was discussed from modifications of "A", "B", and "C" rings and the linker. Preliminary mechanism of action studies indicated that these compounds exert their anticancer activity through inhibition of tubulin polymerization.