Click Chemistry: Diverse Chemical Function from a Few Good Reactions

Kolb, Hartmuth C.; Finn, M G; Sharpless, K. Barry; Chakraborty, Saumen

doi:10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5

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Click Chemistry: Diverse Chemical Function from a Few Good Reactions

Author(s): Hartmuth C. Kolb , M. G. Finn , K. Barry Sharpless

Publication date Created: June 01 2001

Publication date (Print): June 01 2001

Journal: Angewandte Chemie International Edition

Publisher: Wiley-Blackwell

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Catalytic Asymmetric Dihydroxylation

Hartmuth Kolb, Michael S. VanNieuwenhze, K. Sharpless (1994)

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The atom economy--a search for synthetic efficiency

B. TROST (1991)

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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).

T Penning, J J Talley, S Bertenshaw … (1997)

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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Journal

Title: Angewandte Chemie International Edition

Abbreviated Title: Angew. Chem. Int. Ed.

Publisher: Wiley-Blackwell

ISSN (Print): 1433-7851

ISSN (Electronic): 1521-3773

Publication date Created: June 01 2001

Publication date (Print): June 01 2001

Volume: 40

Issue: 11

Pages: 2004-2021

Article

DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5

PubMed ID: 11433435

SO-VID: d7d3f38f-2445-4b13-a242-ad68232f8f13

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

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Click Chemistry: Diverse Chemical Function from a Few Good Reactions

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Probing cerebral hemodynamics with BOLD fMRI

Most cited references 158

Catalytic Asymmetric Dihydroxylation

The atom economy--a search for synthetic efficiency

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).

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