97852-89-6

Basic information

• Product Name: 5-[(3,4-dihydroxyphenyl)methylene]-2-thioxo-4-Thiazolidinone
• Synonyms: 5-(3,4-Dihydroxybenzylidene)rhodanine,5-(3,4-Dihydroxybenzylidene)rhodanine
• CAS NO: 97852-89-6
• Molecular Formula: C10H7NO3S2
• Molecular Weight: 253.302
• Mol File: 97852-89-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: >270 °C
• Density: 1.70±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 5-[(3,4-dihydroxyphenyl)methylene]-2-thioxo-4-Thiazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(3,4-dihydroxyphenyl)methylene]-2-thioxo-4-Thiazolidinone(97852-89-6)
• EPA Substance Registry System: 5-[(3,4-dihydroxyphenyl)methylene]-2-thioxo-4-Thiazolidinone(97852-89-6)

Safety Data

• Hazardous Substances Data: 97852-89-6(Hazardous Substances Data)

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 1415582-13-6 C₁₁H₉NO₃S₂ 
• 1415582-39-6 (5Z,5'Z)-2,2'-(heptane-1,7-diyldiimino)bis(5-(3,4-dihydroxybenzylidene)-1,3-thiazol-4(5H)-one) 
• 857760-57-7 3-(3,4-dihydroxy-phenyl)-2-thioxo-propionic acid 

Relevant articles and documents

Design and microwave synthesis of new (5z) 5-arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5z) 2-amino-5-arylidene-1,3-thiazol-4(5h)-one as new inhibitors of protein kinase dyrk1a

Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradi

New compounds having skin whitening, antioxidant and PPAR activity, and medical use thereof

PURPOSE: A novel compound with skin whitening, antioxidation, and PPAR activation effects, and a medical use thereof are provided to be used for a pharmaceutical composition or a cosmetic product. CONSTITUTION: A compound is denoted by chemical formula 1. A skin whitening composition contains the compound as an active ingredient. An antioxidative composition for preventing or treating oxidative diseases contains the compound of chemical formula 1 as an active ingredient. The oxidative diseases are selected among skin aging, pigmentation, wrinkling, psoriasis, or eczema. The composition prevents or treats diseases which are regulated by PPAR(peroxisome proliferator-activated receptor) activity. The PPAR includes PPAR alpha or PPAR gamma.

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.