Thiolactones are a class of heterocyclic compounds in organic chemistry. They are analogs of the more common lactones in which an oxygen atom is replaced with a sulfur atom. The sulfur atom is within the ring system and adjacent to a carbonyl group.
Chemistry
Thiolactones can be prepared by dehydration of thiol-containing carboxylic acids. Thiolactones can be hydrolyzed back to the thiol acids under basic conditions.[1] β-Thiolactones can be opened by reaction at the 4-position via SN2 nucleophilic reactions.[2]
Occurrence
Thiolactones are intermediates in the activation of some drugs.[4]
^Stevens, Charles; Tarbell, D. Stanley (December 1954). "The Kinetics of Basic Hydrolysis Of Some γ-Lactones and γ-Thiolactones In Aqueous Acetone". The Journal of Organic Chemistry. 19 (12): 1996–2003. doi:10.1021/jo01377a017.
^
Pereillo JM, Maftouh M, Andrieu A, Uzabiaga MF, Fedeli O, Savi P, Pascal M, Herbert JM, Maffrand JP, Picard C (2002). "Structure and stereochemistry of the active metabolite of clopidogrel". Drug Metab. Dispos. 30 (11): 1288–95. doi:10.1124/dmd.30.11.1288. PMID12386137. S2CID2493588.
^Farid, Nagy A.; Kurihara, Atsushi; Wrighton, Steven A. (2010). "Metabolism and Disposition of the Thienopyridine Antiplatelet Drugs Ticlopidine, Clopidogrel, and Prasugrel in Humans". The Journal of Clinical Pharmacology. 50 (2): 126–142. doi:10.1177/0091270009343005. PMID19948947.