4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity
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4-Oxothiazolidine core, owing to the wide range of pharmacological activities exhibited by its derivatives, has been recognized as an important structural motif in biologically active compounds. A subclass constitutes 4-oxothiazolidines with an exocyclic C=C double bond at the C(2)-position. Some of these derivatives are registered as active substances for the treatment of various diseases, such as Ralitoline, an antiepileptic, Etozolin, a diuretic, and Piprozolin, a choleretic. The exocyclic C=C double bond in these compounds contains one or two electron-accepting groups at its other end, so that they also belong to the class of the so-called push-pull alkenes. In the case of the nitrogen-unsubstituted molecules, the enamino tautomeric form with the exocyclic double bond is stabilized by the extended electron delocalization arising from the push-pull effect. In the absence of push-pull effect, the imino form would dominate. Therefore, these compounds exhibit properties characteristic ...for both 4-oxothiazolidine ring and push-pull alkenes. They are also proved to be useful synthetic interamediates for the formation of various mono- and polyheterocycles. The importance of 4-oxothiazolidine derivatives is witnessed by several review articles, the latest published in 2012, mainly dealing with the chemistry and biological activity of various 2-imino, 2-oxo, 2-thioxo and 2-alkyl(aryl)-substituted compounds. The lack of a comprehensive review on 2-alkylidene-4-oxothiazolidines has prompted us to collect the literature covering their synthesis, structure, reactivity and biological activity. Derivatives with two exocyclic C=C double bonds are included, too.
Keywords:2-Alkylidene-4-oxothiazolidine / biological activity / heterocycle / push-pull alkene / reactivity / structure / synthesis
Source:Current Organic Chemistry, 2014, 18, 9, 1108-1148
- Bentham Science Publ Ltd, Sharjah