Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx super([registered]) and Arcoxia super([registered])

The preparation of the sulfoxide analogues 2 and 4, and their enantiomeric pure forms is discussed as well as their potential to act as prodrugs to the potent and selective sulfone-containing COX-2 inhibitors rofecoxib and etoricoxib. Sulfoxides 2 and 4 were shown to be effectively transformed in vi...

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Published inBioorganic & medicinal chemistry letters Vol. 16; no. 12; pp. 3209 - 3212
Main Authors Caturla, Francisco, Amat, Merce, Reinoso, Raquel F, Cordoba, Monica, Warrellow, Graham
Format Journal Article
LanguageEnglish
Published 01.06.2006
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Summary:The preparation of the sulfoxide analogues 2 and 4, and their enantiomeric pure forms is discussed as well as their potential to act as prodrugs to the potent and selective sulfone-containing COX-2 inhibitors rofecoxib and etoricoxib. Sulfoxides 2 and 4 were shown to be effectively transformed in vivo into rofecoxib and etoricoxib, respectively, after oral administration in rats. In the case of sulfoxide 2, both a slightly improved pharmacokinetic profile and a better pharmacological activity in an arthritis model were seen when compared with rofecoxib.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2006.03.052