Rhodanine

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Not to be confused with rhodamine.
Rhodanine[1]
Rhodanine transparant.png
Names
IUPAC name
2-Sulfanylidene-1,3-thiazolidin-4-one
Other names
2-Thioxo-4-thiazolidinone; 4-Oxo-2-thioxothiazoline
Identifiers
141-84-4 YesY
ChEMBL ChEMBL224633 YesY
ChemSpider 1013337 YesY
Jmol-3D images Image
PubChem 1201546
Properties
C3H3NOS2
Molar mass 133.19 g·mol−1
Melting point 165 to 169 °C (329 to 336 °F; 438 to 442 K)
Hazards
EU classification Harmful Xn
R-phrases R22 R41
S-phrases S22 S26 S39
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Rhodanine is an organic compound derived from thiazolidine. Rhodanine can be prepared by the reaction of carbon disulfide, ammonia, and chloroacetic acid.[2]

Some rhodanine derivatives have pharmacological properties; for instance, epalrestat is used to treat diabetic neuropathy. However, most are promiscuous binders with poor selectivity; as a result, this class of compounds is viewed with suspicion by medicinal chemists.[3][4]

References[edit]

  1. ^ Rhodanine at Sigma-Aldrich
  2. ^ C. Ernst Redemann; Roland N. Icke; Gordon A. Alles (1955). "Rhodanine". Org. Synth. ; Coll. Vol. 3, p. 763 
  3. ^ J.B. Baell, G.A. Holloway (2010). "New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays". J. Med. Chem. 53 (7): 2719–2740. doi:10.1021/jm901137j. PMID 20131845. 
  4. ^ Tomašić, Tihomir; Peterlin Mašič, Lucija (2012). "Rhodanine as a scaffold in drug discovery: A critical review of its biological activities and mechanisms of target modulation". Expert Opinion on Drug Discovery: 1. doi:10.1517/17460441.2012.688743.