Abstract
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.
MeSH terms
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Animals
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Crystallography, X-Ray
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Cyclooxygenase 1 / drug effects
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Cyclooxygenase 2 / drug effects*
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Cyclooxygenase 2 Inhibitors / chemical synthesis
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Cyclooxygenase 2 Inhibitors / chemistry
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Cyclooxygenase 2 Inhibitors / pharmacology*
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Drug Evaluation, Preclinical
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Humans
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Male
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Models, Molecular
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Molecular Structure
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Prodrugs / chemical synthesis
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Prodrugs / chemistry
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Prodrugs / pharmacology*
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Rats
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Rats, Wistar
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Stereoisomerism
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Structure-Activity Relationship
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Sulfones / chemical synthesis
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Sulfones / chemistry
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Sulfones / pharmacology*
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Sulfoxides / chemical synthesis
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Sulfoxides / chemistry
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Sulfoxides / pharmacology*
Substances
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Cyclooxygenase 2 Inhibitors
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Prodrugs
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Sulfones
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Sulfoxides
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Cyclooxygenase 1
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Cyclooxygenase 2