37530-35-1

Basic information

• Product Name: 5-(3-HYDROXY-BENZYLIDENE)-2-THIOXO-THIAZOLIDIN-4-ONE
• Synonyms: (5E)-5-(3-hydroxybenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one;(5E)-5-(3-hydroxybenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one(SALTDATA: FREE);(5E)-5-(3-Hydroxybenzylidene)-2-Mercapto-thiazol-4(5H)-one;(5E)-5-(3-hydroxybenzylidene)-2-thioxo-thiazolidin-4-one;(5E)-5-[(3-hydroxyphenyl)methylene]-2-thioxo-4-thiazolidinone;(5E)-5-[(3-hydroxyphenyl)methylene]-2-thioxo-thiazolidin-4-one;(5E)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one;(E)-5-(3-Hydroxybenzylidene)-2-mercaptothiazol-4(5H)-one
• CAS NO: 37530-35-1
• Molecular Formula: C₁₀H₇NO₂S₂
• Molecular Weight: 237.3
• Mol File: 37530-35-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 244 °C (decomp)
• Boiling Point: 440.1°C at 760 mmHg
• Flash Point: 220°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 2.34E-08mmHg at 25°C
• Refractive Index: 1.776
• Storage Temp.: 2-8°C
• PKA: 7.50±0.30(Predicted)
• CAS DataBase Reference: 5-(3-HYDROXY-BENZYLIDENE)-2-THIOXO-THIAZOLIDIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-HYDROXY-BENZYLIDENE)-2-THIOXO-THIAZOLIDIN-4-ONE(37530-35-1)
• EPA Substance Registry System: 5-(3-HYDROXY-BENZYLIDENE)-2-THIOXO-THIAZOLIDIN-4-ONE(37530-35-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 37530-35-1(Hazardous Substances Data)

Usage

General Description

5-(3-HYDROXY-BENZYLIDENE)-2-THIOXO-THIAZOLIDIN-4-ONE is a chemical compound with the molecular formula C11H9NOS2. It is a thiazolidinone derivative with a benzylidene substitution at the fifth position and a thioxo group at the second position. 5-(3-HYDROXY-BENZYLIDENE)-2-THIOXO-THIAZOLIDIN-4-ONE has shown potential biological activities, such as anti-inflammatory and antioxidant properties. It has been studied for its potential use in the treatment of various diseases, including cancer and diabetes. Additionally, its structural features make it a candidate for further drug development and medicinal chemistry research.

InChI:InChI=1/C10H7NO2S2/c12-7-3-1-2-6(4-7)5-8-9(13)11-10(14)15-8/h1-5,12H,(H,11,13,14)/b8-5+

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 100-83-4 meta-hydroxybenzaldehyde 

Relevant articles and documents

Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry

Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.

Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2

The identification, synthesis and evaluation of a series of rhodanine and thiazolidin-2,4-dione derivatives as selective inhibitors of human arylamine N-acetyltransferase 1 and mouse arylamine N-acetyltransferase 2 is described. The most potent inhibitors

COMPOUNDS USEFUL AS HYPOGLYCEMIC AGENTS AND FOR TREATING ALZHEIMER'S DISEASE

Provided are methods for treating hyperglycemia and Alzheimer's disease utilizing certain rhodanine derivatives. Certain of the rhodanine derivatives utilized in the instant methods are novel and, accordingly, such compounds and pharmaceutical formulation