Synthesis and in solution behaviour of new 2‐substituted‐4‐thiazolidinecarboxylic acid derivatives

Abstract

A number of 2‐substituted‐4‐thiazolidinecarboxylic acid derivatives were synthesized by cyclocondensation of L‐cysteine or its esters with various aldehydes, resulting from acids provided with antiinflammatory properties. In the cyclocondensation a new chiral center at C‐2 position of thiazolidine ring is formed giving rise to a mixture of diastereoisomers which can be partially separated. These diastereoisomers show in solution a fast epimerisation at the same chiral center as evidenced by 1H‐nmr studies.

Microbiological Transformations 43. Epoxide Hydrolases as Tools for the Synthesis of Enantiopure α-Methylstyrene Oxides: A New and Efficient Synthesis of (S)-Ibuprofen

“…The overall yield of 8 , starting from racemic 5 , amounted to 35%. [α] 20 D : −16 ( c 1.0, CHCl 3 ) (lit . [α] 20 D −14.8 ( c 1.6; CHCl 3 )).…”

Regioselectivity of the hydrolysis of 2-(1-alkoxyvinyl)-substituted imidazolidines, 1,3-thiazolidines, and 1,3-oxazolidines

“…Hydrolytic stability of the above listed heterocyclic compounds is an important factor determining their application as therapeutic agents which undergo cleavage of the heteroring in vivo [10,11]. It is known that L-cysteine responsible for intracellular level of glutathione could be introduced at a required dose as appropriate prodrugs, 2-alkylthiazolidines [10,11].…”

“…It is known that L-cysteine responsible for intracellular level of glutathione could be introduced at a required dose as appropriate prodrugs, 2-alkylthiazolidines [10,11]. The nitrogen-containing heteroring in vivo undergoes nonenzymatic hydrolysis to release amino acid and the corresponding aldehyde.…”

“…2-Alkylthiazolidines exhibit radioprotective, antimutagenic, antibacterial, and antiviral activity [3,8]. Compounds of the thiazolidine series are important as models for studying biochemical transformations of their complex analogs involved in natural processes [9].Hydrolytic stability of the above listed heterocyclic compounds is an important factor determining their application as therapeutic agents which undergo cleavage of the heteroring in vivo [10,11]. It is known that L-cysteine responsible for intracellular level of glutathione could be introduced at a required dose as appropriate prodrugs, 2-alkylthiazolidines [10,11].…”