Thiazolidine is a heterocyclic organic compound with the formula (CH2)3(NH)S. It is a 5-membered saturated ring with a thioether group and an amine group in the 1 and 3 positions. It is a sulfur analog of oxazolidine. Thiazolidine is a colorless liquid. Although the parent thiazolidine is only of academic interest, some derivatives, i.e., the thiazolidines, are important, such as the antibiotic penicillin.
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Preferred IUPAC name
1,3-Thiazolidine[1] | |
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ECHA InfoCard | 100.007.275 |
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Properties | |
C3H7NS | |
Molar mass | 89.16 g·mol−1 |
Density | 1.131 g/cm3[2] |
Boiling point | 72 to 75 °C (162 to 167 °F; 345 to 348 K)[2] 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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Thiazolidine is prepared by the condensation of cysteamine and formaldehyde.[3] Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine (thioproline), derived from formaldehyde and cysteine.
Useful thiazolidines include the drug pioglitazone, the antibiotic penicillin, and N-Methyl-2-thiazolidinethione, an accelerator for the vulcanization of chloroprene rubbers.[4]
Thiazolidines functionalized with carbonyls at the 2 and 4 positions, the thiazolidinediones, are drugs used in the treatment of diabetes mellitus type 2. Rhodanine is a related bioactive species, featuring one carbonyl and one thiocarbonyl.
Many thiazolidines are prepared from cysteine and related aminothiols.[5] p-aminocinnamaldehyde is able to differentiate between cysteine and homocysteine. With cysteine, a buffered water solution of the aldehyde changes from yellow to colorless due to a secondary ring closing reaction of the imine. Homocysteine is unable to give ring closure and the color does not change.