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 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL224633 Y
ChemSpider	1013337 Y
ECHA InfoCard	100.005.005
PubChem	1201546
InChI InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) Y Key: KIWUVOGUEXMXSV-UHFFFAOYSA-N Y 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).
Y verify (what is YN ?)
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