31061-24-2

Basic information

• Product Name: (2,4-DIOXO-1,3-THIAZOLIDIN-3-YL)ACETIC ACID
• Synonyms: (2,4-dioxo-1,3-thiazolidin-3-yl)acetic acid(SALTDATA: FREE);AKOS BBS-00000977;(2,4-DIOXO-THIAZOLIDIN-3-YL)-ACETIC ACID;(2,4-DIOXO-1,3-THIAZOLIDIN-3-YL)ACETIC ACID;ART-CHEM-BB B023305;IFLAB-BB F1074-0394;CHEMBRDG-BB 4004600;OTAVA-BB BB7211360003
• CAS NO: 31061-24-2
• Molecular Formula: C₅H₅NO₄S
• Molecular Weight: 175.16
• Mol File: 31061-24-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 379°C at 760 mmHg
• Flash Point: 183°C
• Appearance: /
• Density: 1.676g/cm³
• Vapor Pressure: 8.6E-07mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Sonicated), DMSO (Slightly)
• PKA: 3.75±0.10(Predicted)
• CAS DataBase Reference: (2,4-DIOXO-1,3-THIAZOLIDIN-3-YL)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4-DIOXO-1,3-THIAZOLIDIN-3-YL)ACETIC ACID(31061-24-2)
• EPA Substance Registry System: (2,4-DIOXO-1,3-THIAZOLIDIN-3-YL)ACETIC ACID(31061-24-2)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 31061-24-2(Hazardous Substances Data)

Usage

Uses

(2,4-Dioxo-thiazolidin-3-yl)-acetic Acid is a useful compound for preparation of novel thiazolidinedione-?hydroxamates as Zmp1 inhibitors.

InChI:InChI=1/C5H5NO4S/c7-3-2-11-5(10)6(3)1-4(8)9/h1-2H2,(H,8,9)

Upstream product

• 18345-22-7 (2,4-dioxothiazolidin-3-yl)acetic acid methyl ester 
• 2295-31-0 thiazoline-2,4-dione 
• 616-27-3 1-chlorobutan-2-one 
• 79-08-3 bromoacetic acid 
• 39137-34-3 (2,4-thiazolidinedion-3-yl)acetic acid ethyl ester 
• 50773-27-8 (2,4-dioxothiazolidin-3-yl)acetic acid tert-butyl ester 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 466652-58-4 C₁₃H₁₁O₆SN 
• 1452759-66-8 (Z)-2-(5-(2-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)acetic acid 
• 1452759-67-9 (Z)-2-(5-(2,3-dichlorobenzylidene)-2,4-dioxothizolidin-3-yl)acetic acid 
• 1452759-68-0 (Z)-2-(5-(2-chloro-5-nitrobenzylidene)-2,4-dioxothizolidin-3-yl)acetic acid 
• 1452759-69-1 (Z)-2-(5-(4-chloro-3-nitrobenzylidene)-2,4-dioxothizolidin-3-yl)acetic acid 
• 1452759-70-4 (Z)-2-(5-(2-3-dihydroxybenzylidene)-2,4-dioxothizolidin-3-yl)acetic acid 
• 1452759-72-6 (Z)-2-(5-(3,5-dibromo-4-hydroxybenzylidene)-2,4-dioxothizolidin-3-yl)acetic acid 
• 1452759-73-7 (Z)-2-(5-(4-bromo-2-fluorobenzylidene)-2,4-dioxothizolidin-3-yl)acetic acid 
• 1452759-74-8 (Z)-2-(5-(4-bromo-3-fluorobenzylidene)-2,4-dioxothizolidin-3-yl)acetic acid 
• 1452759-75-9 (Z)-2-(5-(2,4-dinitrobenzylidene)-2,4-dioxothizolidin-3-yl)-acetic acid 

Relevant articles and documents

A Combinatorial Virtual Screening Approach Driving the Synthesis of 2,4-Thiazolidinedione-Based Molecules as New Dual mPGES-1/5-LO Inhibitors

Dual inhibition of microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO), two key enzymes involved in pro-inflammatory eicosanoid biosynthesis, represents a new strategy for treating inflammatory disorders. Herein we report the discovery of 2,4-thiazolidinedione-based mPGES-1/5-LO dual inhibitors following a multidisciplinary protocol, involving virtual combinatorial screening, chemical synthesis, and validation of the biological activities for the selected compounds. Following the multicomponent-based chemical route for the decoration of the 2,4-thiazolidinedione core, a large library of virtual compounds was built (～2.0×104 items) and submitted to virtual screening. Nine selected molecules were synthesized and biologically evaluated, disclosing among them four compounds able to reduce the activity of both enzymes in the mid- and low- micromolar range of activities. These results are of interest for further expanding the chemical diversity around the 2,4-thiazolidinedione central core, facilitating the identification of novel anti-inflammatory agents endowed with a promising and safer pharmacological profile.

Novel thiazolidinedione-hydroxamates as inhibitors of Mycobacterium tuberculosis virulence factor Zmp1

Zinc metalloprotease 1 (Zmp1) is an extracellular enzyme, which has been found essential for the intracellular survival and pathogenesis of Mycobacterium tuberculosis. In this work, we designed and synthesized a series of novel thiazolidinedione-hydroxamates and evaluated in silico their drug-likeness behavior. Then, their inhibitory properties towards a recombinant Zmp1 from Mycobacterium tuberculosis were analyzed by MALDI-TOF MS. Nine of the tested compounds were found to inhibit the enzymatic reaction more effectively than the generic metalloprotease inhibitor phosphoramidon. Furthermore, the synthesized thiazolidinedione-hydroxamate hybrids were evaluated for their in vitro antimycobacterial activity and acute cytotoxicity using whole-cell assays. Results showed that none of the hybrids exhibited acute cytotoxicity against RAW264.7 macrophages. Whereas extracellular antimycobacterial activity was limited, RAW264.7 macrophage infection results showed that a majority of the hybrids inhibited the intracellular growth of Mycobacterium tuberculosis at a concentration of 100 and 10 μM. The thiazolidinedione-hydroxamate compound 2n was considered to be the best candidate of the evaluated library.

HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY

The present invention relates to certain heterocyclic compounds of formula (1) that have the ability to inhibit lysine biosynthesis via the diaminopimelate biosynthesis pathway in certain organisms. As a result of this activity these compounds can be used