Design and synthesis of novel celecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of the sulfonamide pharmacophore by a sulfonylazide bioisostere

Penning, 1997, J. Med. Chem., 40, 1347, 10.1021/jm960803q Goldstein, 2000, Am. J. Gastroenterol., 95, 1681, 10.1111/j.1572-0241.2000.02194.x Kurumbail, 1996, Nature, 384, 644, 10.1038/384644a0 Luong, 1996, Nat. Struct. Biol., 3, 927, 10.1038/nsb1196-927 Llorens, 1999, Bioorg. Med. Chem. Lett., 9, 2779, 10.1016/S0960-894X(99)00481-3 Garavito, 1999, Biochim. Biophys. Acta, 1441, 278, 10.1016/S1388-1981(99)00147-X Habeeb, 2001, J. Med. Chem., 44, 3039, 10.1021/jm010153c Habeeb, 2001, J. Med. Chem., 44, 2921, 10.1021/jm0101287 Rahim, 2002, Bioorg. Med. Chem. Lett., 12, 2753, 10.1016/S0960-894X(02)00537-1 Gilbert, 1969, Synthesis, 3, 10.1055/s-1969-34188 Leffler, 1962, J. Org. Chem., 28, 902, 10.1021/jo01039a004 Soliman, 1979, J. Med. Chem., 22, 321, 10.1021/jm00189a022 Hashimoto, 2002, J. Med. Chem., 45, 1511, 10.1021/jm010484p Alchemy 2000 (program), Version 2.0; Tripos Inc.: St. Louis, MO, USA. Lieber, 1966, Chem. Ind., 586 Pauling, L. In The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960. Livingston, 1960, J. Phys. Chem., 64, 756, 10.1021/j100835a012 Greig, 1997, Mol. Pharmacol., 52, 829, 10.1124/mol.52.5.829 Selinsky, 2001, Biochemistry, 40, 5172, 10.1021/bi010045s Price, 2000, J. Am. Chem. Soc., 122, 9455, 10.1021/ja001018c Insight II, Version 97 and Discover, Version 2.98; Molecular Simulations, Inc: San Diego, CA, USA, 1997. Habeeb, 2000, Drug Dev. Res., 51, 273, 10.1002/ddr.9