Summary.
The synthesis of three thiophene analogues of Flosulide – a potent and selective inhibitor of cyclooxygenase subtype 2 (COX-2) – is described. Utilizing combined Friedel-Crafts acylation and alkylation of 2-chlorothiophene, simplified procedures were developed to obtain cyclopenta[b]- thiophenones as key products which were further derivatized by nitration, nucleophilic aromatic substitution, reduction, and mesylation.
Zusammenfassung.
Die Synthese dreier Thiophenanaloga von Flosulid – ein potenter und selektiver Hemmer der Cyclooxygenase vom Subtyp 2 (COX-2) – wird beschrieben. Durch Anwendung kombinierter Friedel-Crafts-Acylierung und -Alkylierung von 2-Chlorthiophen wurden vereinfachte Verfahren zur Herstellung von Cyclopenta[b]thiophenen als Schlüsselsubstanzen entwickelt, welche weiter durch Nitrierung, nucleophile aromatische Substitution, Reduktion und Mesylierung derivatisiert wurden.
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Received February 23, 1998. Accepted (revised) May 14, 1998
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Binder, D., Pyerin, M., Steindl, R. et al. A Facile Route to Functionalized Cyclopenta[b]thiophenones Based on the Structure of the Selective COX-2 Inhibitor Flosulide. Monatshefte fuer Chemie 129, 887–896 (1998). https://doi.org/10.1007/PL00013496
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DOI: https://doi.org/10.1007/PL00013496