Rhodanine

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Rhodanine[1]
Rhodanine.svg
Names
IUPAC name
2-Sulfanylidene-1,3-thiazolidin-4-one
Other names
2-Thioxo-4-thiazolidinone; 4-Oxo-2-thioxothiazoline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.005
Properties
C3H3NOS2
Molar mass 133.18 g·mol−1
Melting point 165 to 169 °C (329 to 336 °F; 438 to 442 K)
Hazards
Harmful Xn
R-phrases (outdated) R22 R41
S-phrases (outdated) S22 S26 S39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Rhodanine is a 5-membered heterocyclic organic compound possessing a thiazolidine core. It was first discovered in 1877 by Marceli Nencki who named it "Rhodaninsaure" in reference to its synthesis from ammonium rhodanide (in modern chemistry ammonium thiocyanate) and chloroacetic acid in water.[2]

Rhodanines can also be prepared by the reaction of carbon disulfide, ammonia, and chloroacetic acid, which proceeds via an intermediate dithiocarbamate.[3]

Rhodanine synthesis.png

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,[4][5][6]

References[edit]

  1. ^ Rhodanine at Sigma-Aldrich
  2. ^ Nencki, M. (10 July 1877). "Ueber die Einwirkung der Monochloressigsäure auf Sulfocyansäure und ihre Salze". Journal fur Praktische Chemie. 16 (1): 1–17. doi:10.1002/prac.18770160101. 
  3. ^ C. Ernst Redemann; Roland N. Icke; Gordon A. Alles (1955). "Rhodanine". Org. Synth. ; Coll. Vol., 3, p. 763 
  4. ^ 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. PMID 20131845. doi:10.1021/jm901137j. 
  5. ^ 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. 7: 1. doi:10.1517/17460441.2012.688743. 
  6. ^ Pouliot, Martin; Jeanmart, Stephane (8 September 2015). "Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research". Journal of Medicinal Chemistry. 59: 150908163303002. PMID 26313340. doi:10.1021/acs.jmedchem.5b00361.