Rhodanine

Rhodanine^[1]

Names
IUPAC name 2-Sulfanylidene-1,3-thiazolidin-4-one
Other names 2-Thioxo-4-thiazolidinone; 4-Oxo-2-thioxothiazoline
Identifiers
CAS Number	141-84-4
ChEMBL	ChEMBL224633
ChemSpider	1013337
Jmol interactive 3D	Image
PubChem	1201546
InChI InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) Key: KIWUVOGUEXMXSV-UHFFFAOYSA-N InChI=1/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) Key: KIWUVOGUEXMXSV-UHFFFAOYAP
SMILES O=C1NC(=S)SC1
Properties
Chemical formula	C3H3NOS2
Molar mass	133.18 g·mol^−1
Melting point	165 to 169 °C (329 to 336 °F; 438 to 442 K)
Hazards
EU classification (DSD)	Xn
R-phrases	R22 R41
S-phrases	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]

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

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. doi:10.1021/jm901137j. PMID 20131845.
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: 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: 150908163303002. doi:10.1021/acs.jmedchem.5b00361.