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Volumn 51, Issue 15, 2008, Pages 4476-4481

Synthesis, biological evaluation, and enzyme docking simulations of 1,5-diarylpyrrole-3-alkoxyethyl ethers as selective cyclooxygenase-2 inhibitors endowed with anti-inflammatory and antinociceptive activity

Author keywords

[No Author keywords available]

Indexed keywords

CARRAGEENAN; CELECOXIB; CYCLOOXYGENASE 2 INHIBITOR; PYRROLE DERIVATIVE; ROFECOXIB; VALDECOXIB;

EID: 49449083101     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800084s     Document Type: Article
Times cited : (58)

References (29)
  • 1
    • 0033551847 scopus 로고    scopus 로고
    • Arachidonic Acid Oxygenation by COX-1 and COX-2: Mechanisms of Catalysis and Inhibition
    • Marnett, L. J.; Rowlinson, S. W.; Goodwin, D. C.; Kalgutkar, A. S,; Lanzo, C.A. Arachidonic Acid Oxygenation by COX-1 and COX-2: Mechanisms of Catalysis and Inhibition. J. Biol. Chem. 1999, 274, 22903-22906.
    • (1999) J. Biol. Chem , vol.274 , pp. 22903-22906
    • Marnett, L.J.1    Rowlinson, S.W.2    Goodwin, D.C.3    Kalgutkar, A.S.4    Lanzo, C.A.5
  • 2
    • 0028810964 scopus 로고
    • Comparison of Hydroperoxide Initiator Requirements for the Cyclooxygenase Activities of Prostaglandin H Synthase-1 and -2
    • Kulmacz, R. J.; Wang, L. H. Comparison of Hydroperoxide Initiator Requirements for the Cyclooxygenase Activities of Prostaglandin H Synthase-1 and -2. J. Biol. Chem. 1995, 270, 24019-24023.
    • (1995) J. Biol. Chem , vol.270 , pp. 24019-24023
    • Kulmacz, R.J.1    Wang, L.H.2
  • 3
    • 0028199075 scopus 로고
    • Ligand-Induced Prostaglandin Synthesis Requires Expression of the TIS10/PGS-2 Prostaglandin Synthase Gene in Murine Fibroblasts and Macrophages
    • Reddy, S. T.; Herschman, H. R. Ligand-Induced Prostaglandin Synthesis Requires Expression of the TIS10/PGS-2 Prostaglandin Synthase Gene in Murine Fibroblasts and Macrophages. J. Biol. Chem. 1994, 269, 15473-15480.
    • (1994) J. Biol. Chem , vol.269 , pp. 15473-15480
    • Reddy, S.T.1    Herschman, H.R.2
  • 5
    • 4143107932 scopus 로고    scopus 로고
    • Cyclooxygenase Isozymes: The Biology of Prostaglandin Synthesis and Inhibition
    • Simmons, D. L.; Botting, R. M.; Hla, T. Cyclooxygenase Isozymes: The Biology of Prostaglandin Synthesis and Inhibition. Pharmacol Rev. 2004, 56, 387-437.
    • (2004) Pharmacol Rev , vol.56 , pp. 387-437
    • Simmons, D.L.1    Botting, R.M.2    Hla, T.3
  • 7
    • 0035833502 scopus 로고    scopus 로고
    • The Coxibs, Selective Inhibitors of Cyclooxygenase-2
    • Fitzgerald, G. A.; Patrono, C. The Coxibs, Selective Inhibitors of Cyclooxygenase-2. N. Engl. J. Med. 2001, 345, 433-442.
    • (2001) N. Engl. J. Med , vol.345 , pp. 433-442
    • Fitzgerald, G.A.1    Patrono, C.2
  • 8
    • 0033577982 scopus 로고    scopus 로고
    • Gastrointestinal Toxicity of Nonsteroidal Anti-Inflammatory Drugs
    • Wolfe, M. M.; Lichtenstein, D. R.; Singh, G. Gastrointestinal Toxicity of Nonsteroidal Anti-Inflammatory Drugs. N. Engl. J. Med. 1999, 340, 1888-1899.
    • (1999) N. Engl. J. Med , vol.340 , pp. 1888-1899
    • Wolfe, M.M.1    Lichtenstein, D.R.2    Singh, G.3
  • 9
    • 0032916736 scopus 로고    scopus 로고
    • DeWitt, D. L. Cox-2-Selective Inhibitors: The New Super Aspirins. Mol. Pharm. 1999, 55, 625-631.
    • DeWitt, D. L. Cox-2-Selective Inhibitors: The New Super Aspirins. Mol. Pharm. 1999, 55, 625-631.
  • 10
    • 31044441042 scopus 로고    scopus 로고
    • Biological Basis for the Cardiovascular Consequences of COX-2 Inhibition: Therapeutic Challenges and Opportunities
    • Grosser, T.; Fries, S.; Fitzgerald, G. A. Biological Basis for the Cardiovascular Consequences of COX-2 Inhibition: Therapeutic Challenges and Opportunities. J. Clin. Invest. 2006, 116, 4-15.
    • (2006) J. Clin. Invest , vol.116 , pp. 4-15
    • Grosser, T.1    Fries, S.2    Fitzgerald, G.A.3
  • 12
    • 33750934205 scopus 로고    scopus 로고
    • The Ever Growing Story of Cyclooxygenase Inhibition
    • Rodriguez, L. A.; Patrignani, P. The Ever Growing Story of Cyclooxygenase Inhibition. Lancet 2006, 368, 1745-1747.
    • (2006) Lancet , vol.368 , pp. 1745-1747
    • Rodriguez, L.A.1    Patrignani, P.2
  • 14
    • 0029008617 scopus 로고
    • Expression of Prostaglandin G/H Synthase-1 and -2 Protein in Human Colon Cancer
    • Kargman, S.; O'Neill, G. P.; Vickers, P. J.; Evans, J. F.; Mancini, J. A.; Jothy, S. Expression of Prostaglandin G/H Synthase-1 and -2 Protein in Human Colon Cancer. Cancer Res. 1995, 55, 2556-2559.
    • (1995) Cancer Res , vol.55 , pp. 2556-2559
    • Kargman, S.1    O'Neill, G.P.2    Vickers, P.J.3    Evans, J.F.4    Mancini, J.A.5    Jothy, S.6
  • 16
    • 33846586530 scopus 로고    scopus 로고
    • Synthesis, Resolution, and Absolute Configuration of two Novel and Selective Cyclooxygenase-2 Inhibitors Based on 1,5-Diarylpyrrole Scaffold
    • Di Bari, L.; Pescitelli, G.; Salvadori, P.; Rovini, M.; Anzini, M.; Cappelli, A.; Vomero, S. Synthesis, Resolution, and Absolute Configuration of two Novel and Selective Cyclooxygenase-2 Inhibitors Based on 1,5-Diarylpyrrole Scaffold. Tetrahedron: Asymmetry 2006, 17, 3430-3436.
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 3430-3436
    • Di Bari, L.1    Pescitelli, G.2    Salvadori, P.3    Rovini, M.4    Anzini, M.5    Cappelli, A.6    Vomero, S.7
  • 19
    • 0030995430 scopus 로고    scopus 로고
    • Differential Allosteric Regulation of Prostaglandin H Synthase-1 and -2 by Arachidonic acid
    • Swinney, D. C.; Mak, A. Y.; Barnett, J.; Ramesha, C. S. Differential Allosteric Regulation of Prostaglandin H Synthase-1 and -2 by Arachidonic acid. J. Biol. Chem. 1997, 272, 12393-12398.
    • (1997) J. Biol. Chem , vol.272 , pp. 12393-12398
    • Swinney, D.C.1    Mak, A.Y.2    Barnett, J.3    Ramesha, C.S.4
  • 20
    • 0036966124 scopus 로고    scopus 로고
    • The Biochemical Selectivity of Novel COX-2 Inhibitors in Whole Blood Assays of COX-Isozyme Activity
    • Tacconelli, S.; Capone, M. L.; Sciulli, M. G.; Ricciotti, E.; Patrignani, P. The Biochemical Selectivity of Novel COX-2 Inhibitors in Whole Blood Assays of COX-Isozyme Activity. Curr. Med. Res. Opin. 2002, 18, 503-511.
    • (2002) Curr. Med. Res. Opin , vol.18 , pp. 503-511
    • Tacconelli, S.1    Capone, M.L.2    Sciulli, M.G.3    Ricciotti, E.4    Patrignani, P.5
  • 24
    • 0023850632 scopus 로고
    • κ-Opioid Agonists Produce Antinociception After iv and icv but not Intrathecal Administration in the Rat
    • Leighton, G. E.; Rodriguez, R. E.; Hill, R. G.; Hughes, J. κ-Opioid Agonists Produce Antinociception After iv and icv but not Intrathecal Administration in the Rat. Br. J. Pharmacol. 1988, 93, 553-560.
    • (1988) Br. J. Pharmacol , vol.93 , pp. 553-560
    • Leighton, G.E.1    Rodriguez, R.E.2    Hill, R.G.3    Hughes, J.4
  • 25
    • 0000680650 scopus 로고
    • Acetic Acid for Analgesic Screening
    • Koster, R.; Anderson, M.; de Beer, E. J. Acetic Acid for Analgesic Screening. Fed. Proc. 1959, 18, 412-418.
    • (1959) Fed. Proc , vol.18 , pp. 412-418
    • Koster, R.1    Anderson, M.2    de Beer, E.J.3
  • 26
    • 11644261806 scopus 로고    scopus 로고
    • Automated Docking Using a Lamarckian Genetic Algorithm and Empirical Binding Free Energy Function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated Docking Using a Lamarckian Genetic Algorithm and Empirical Binding Free Energy Function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 27
    • 14944378770 scopus 로고    scopus 로고
    • Molecular Discovery Ltd, Marsh Road, Pinner, Middlesex, UK
    • Grid, version 21; Molecular Discovery Ltd.: Marsh Road, Pinner, Middlesex, UK.
    • Grid, version 21
  • 29
    • 0242500887 scopus 로고    scopus 로고
    • Theoretical studies on the inhibition mechanism of cyclooxygenase-2. Is there a unique recognition site
    • Soliva, R.; Almansa, C.; Kalko, S. G.; Luque, F. J.; Orozco, M. Theoretical studies on the inhibition mechanism of cyclooxygenase-2. Is there a unique recognition site. J. Med. Chem. 2003, 46, 1372-1382.
    • (2003) J. Med. Chem , vol.46 , pp. 1372-1382
    • Soliva, R.1    Almansa, C.2    Kalko, S.G.3    Luque, F.J.4    Orozco, M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.