Thiazolidine

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Thiazolidine
Thiazolidine numbering.png
Names
IUPAC name
Thiazolidine
Identifiers
504-78-9 YesY
Jmol 3D model Interactive image
PubChem 10444
Properties
C3H7NS
Molar mass 89.16 g·mol−1
Density 1.131 g/cm3[1]
Boiling point 72 to 75 °C (162 to 167 °F; 345 to 348 K)[1] at 25 torr
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

Thiazolidine is a heterocyclic organic compound 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 analog of oxazolidine.

Derivatives, generally referred to as thiazolidines, are known. For example, 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.

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