Rhodanine

Rhodanine^[1]
Names
	Preferred 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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL224633 ;
ChemSpider	1013337 ;
ECHA InfoCard	100.005.005
EC Number	205-505-1;
KEGG	C07280;
PubChem CID	1201546;
UNII	7O50LKL2G8 ;
CompTox Dashboard (EPA)	DTXSID4026002 ;
	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
Density	0.868 g/cm−3
Melting point	170 °C (338 °F; 443 K)
Solubility in water	Soluble
Solubility	Ethanol, dimethyl sulfoxide
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H318
Precautionary statements	P264, P270, P280, P301 P312, P305 P351 P338, P310, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Rhodanine is a 5-membered heterocyclic organic compound possessing a thiazolidine core. It was discovered in 1877 by Marceli Nencki who named it "Rhodaninsaure" in reference to its synthesis from ammonium rhodanide (known as ammonium thiocyanate to modern chemists) and chloroacetic acid in water.^[3]

Rhodanines can also be prepared by the reaction of carbon disulfide, ammonia, and chloroacetic acid, which proceeds via an intermediate dithiocarbamate.^[4]

Derivatives

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.^[5]^[6]^[7] Differing academic opinions exist concerning the correct use of PAINS filters, the necessity of the experimental confirmations of such properties, and many useful features of rhodanine derivatives.^[8]^[9]

References

^ Rhodanine at Sigma-Aldrich
^ ^a ^b ^c ^d Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. p. 3.512. ISBN 978-1439855119.
^ Nencki, M. (10 July 1877). "Ueber die Einwirkung der Monochloressigsäure auf Sulfocyansäure und ihre Salze". Journal für Praktische Chemie. 16 (1): 1–17. doi:10.1002/prac.18770160101.
^ Redemann, C. Ernst; Icke, Roland N.; Alles, Gordon A. (1955). "Rhodanine". Organic Syntheses; Collected Volumes, vol. 3, p. 763.
^ Baell, J. B; Holloway, G. A (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. CiteSeerX 10.1.1.394.9155. doi:10.1021/jm901137j. PMID 20131845.
^ 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 (7): 549–60. doi:10.1517/17460441.2012.688743. PMID 22607309. S2CID 3401210.
^ Pouliot, Martin; Jeanmart, Stephane (8 September 2015). "Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research". Journal of Medicinal Chemistry. 59 (2): 497–503. doi:10.1021/acs.jmedchem.5b00361. PMID 26313340.
^ Kaminskyy, D; Kryshchyshyn, A; Lesyk, R (2017). "Recent developments with rhodanine as a scaffold for drug discovery". Expert Opinion on Drug Discovery. 12 (12): 1233–1252. doi:10.1080/17460441.2017.1388370. PMID 29019278. S2CID 3514481.
^ Kaminskyy, D; Kryshchyshyn, A; Lesyk, R (2017). "5-Ene-4-thiazolidinonese An efficient tool in medicinal chemistry". Eur. J. Med. Chem. 140 (10): 542–863. doi:10.1016/j.ejmech.2017.09.031. PMC 7111298. PMID 28987611.

[1] Rhodanine at Sigma-Aldrich

[b1-2] Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. p. 3.512. ISBN 978-1439855119.

[3] Nencki, M. (10 July 1877). "Ueber die Einwirkung der Monochloressigsäure auf Sulfocyansäure und ihre Salze". Journal für Praktische Chemie. 16 (1): 1–17. doi:10.1002/prac.18770160101.

[4] Redemann, C. Ernst; Icke, Roland N.; Alles, Gordon A. (1955). "Rhodanine". Organic Syntheses; Collected Volumes, vol. 3, p. 763.

[5] Baell, J. B; Holloway, G. A (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. CiteSeerX 10.1.1.394.9155. doi:10.1021/jm901137j. PMID 20131845.

[6] 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 (7): 549–60. doi:10.1517/17460441.2012.688743. PMID 22607309. S2CID 3401210.

[7] Pouliot, Martin; Jeanmart, Stephane (8 September 2015). "Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research". Journal of Medicinal Chemistry. 59 (2): 497–503. doi:10.1021/acs.jmedchem.5b00361. PMID 26313340.

[8] Kaminskyy, D; Kryshchyshyn, A; Lesyk, R (2017). "Recent developments with rhodanine as a scaffold for drug discovery". Expert Opinion on Drug Discovery. 12 (12): 1233–1252. doi:10.1080/17460441.2017.1388370. PMID 29019278. S2CID 3514481.

[9] Kaminskyy, D; Kryshchyshyn, A; Lesyk, R (2017). "5-Ene-4-thiazolidinonese An efficient tool in medicinal chemistry". Eur. J. Med. Chem. 140 (10): 542–863. doi:10.1016/j.ejmech.2017.09.031. PMC 7111298. PMID 28987611.

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