Thiazolidine
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Names | |
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Preferred IUPAC name
1,3-Thiazolidine[1] | |
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3D model (JSmol)
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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 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.
Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin.
Preparation[edit]
Thiazolidine is prepared as it was in its first reported synthesis, by the condensation of cysteamine and formaldehyde.[3] Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine, derived from formaldehyde and cysteine.
Derivatives[edit]
N-Methyl-2-thiazolidinethione is 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.
See also[edit]
References[edit]
- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ a b Thiazolindine
- ^ Ratner, Sarah; Clarke, H. T. (1937). "Action of formaldehyde on cysteine". Journal of the American Chemical Society. 59: 200–6. doi:10.1021/ja01280a050.
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: CS1 maint: uses authors parameter (link) - ^ Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_001. ISBN 3527306730.
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