Thiazolidine

Thiazolidine

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Names
IUPAC name Thiazolidine
Identifiers
CAS Number	504-78-9 Y
Jmol 3D model	Interactive image
PubChem	10444
SMILES C1CSCN1
Properties
Chemical formula	C3H7NS
Molar mass	89.16 g/mol
Density	1.131 g/cm3
Boiling point	72 to 75 °C (162 to 167 °F; 345 to 348 K) at 25 torr
Vapor pressure	{{{value}}}
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

Thiazolidines are a class of heterocyclic organic compounds with a 5-membered saturated ring with a thioether group and an amine group in the 1 and 3 positions, respectively. It is a sulfur analogue of oxazolidine. The drug pioglitazone contains a thiazolidine ring. It is a drug usually indicated in cases of type II diabetes for decreasing blood sugar. It also decreases triglycerides and C-reactive protein levels. It lowers blood pressure and increases levels of HDL. Another drug which contains a thiazolidine ring is the antibiotic drug penicillin.

Thiazolidines may be synthesized by a condensation reaction between a thiol and an aldehyde or ketone. The reaction is reversible. Therefore, many thiazolidines are labile towards hydrolysis in aqueous solution. Hydrolysis of the thiazolidine generates the thiol and aldehyde or ketone from which it was synthesized.

Thiazolidine with 2 ketones (at the 2 and 4 positions) provides the functional group of the thiazolidinediones.