Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors
The enantiomeric synthesis and profiling of sulfoxide-based prodrugs of potent COX-2 inhibitors discovered at Almirall are reported. The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and...
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Published in | Bioorganic & medicinal chemistry letters Vol. 16; no. 13; pp. 3605 - 3608 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Elsevier Ltd
01.07.2006
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | The enantiomeric synthesis and profiling of sulfoxide-based prodrugs of potent COX-2 inhibitors discovered at Almirall are reported.
The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives 1 and 3, after oral administration to rats. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0960-894X 1464-3405 |
DOI: | 10.1016/j.bmcl.2006.03.101 |