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      Click Chemistry: Diverse Chemical Function from a Few Good Reactions

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      Angewandte Chemie International Edition

      Wiley-Blackwell

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          Catalytic Asymmetric Dihydroxylation

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            Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib).

            A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3-(trifluoromethyl)- H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
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              Asymmetric 1,3-Dipolar Cycloaddition Reactions.

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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley-Blackwell
                1433-7851
                1521-3773
                June 01 2001
                June 01 2001
                : 40
                : 11
                : 2004-2021
                Article
                10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
                11433435
                © 2001

                http://doi.wiley.com/10.1002/tdm_license_1.1

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