Thiazolidine

Thiazolidine

Thiazolidine
Names
IUPAC name
Thiazolidine
Identifiers
 YesY
Jmol-3D images Image
PubChem
Properties
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
 YesY  (: YesY/N?)

Thiazolidines are a class of 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.

References