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Volumn 47, Issue 9, 2004, Pages 2180-2193

Synthesis and Selective Cyclooxygenase-2 Inhibitory Activity of a Series of Novel, Nitric Oxide Donor-Containing Pyrazoles

Author keywords

[No Author keywords available]

Indexed keywords

1 [1 CYCLOHEXYL 3 [1 (HYDROXYIMINO) 4 (NITROOXY)BUTYL]PYRAZOL 5 YL] 4 (METHYLSULFONYL)BENZENE; 1 [3 [4 (NITROOXY)BUT 1 ENYL] 1 CYCLOHEXYLPYRAZOL 5 YL] 4 (METHYLSULFONYL)BENZENE; 4 [1 CYCLOHEXYL 3 [3 (NITROOXY)PROPYL]PYRAZOL 5 YL] 1 (METHYLSULFONYL)BENZENE; ACETYLSALICYLIC ACID; BENZENE DERIVATIVE; CARRAGEENAN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; NITRIC OXIDE; OXIME; PYRAZOLE DERIVATIVE; TERT BUTOXY N (CYCLOPENTYLAMINO)CARBOXAMIDE; UNCLASSIFIED DRUG;

EID: 11144354316     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030276s     Document Type: Conference Paper
Times cited : (91)

References (51)
  • 3
    • 0035246513 scopus 로고    scopus 로고
    • Cyclooxygenase inhibitors-current status and future prospects
    • Dannhard, G.; Kiefer, W. Cyclooxygenase inhibitors-current status and future prospects. Eur. J. Med. Chem. 2001, 36, 109-126.
    • (2001) Eur. J. Med. Chem. , vol.36 , pp. 109-126
    • Dannhard, G.1    Kiefer, W.2
  • 4
    • 0033948914 scopus 로고    scopus 로고
    • Inhibitors of cyclooxygenase-2: November 1999 - April 2000
    • Carter, J. S. Inhibitors of cyclooxygenase-2: November 1999 - April 2000. Exp. Opin. Ther. Pat. 2000, 10, 1011-1020.
    • (2000) Exp. Opin. Ther. Pat. , vol.10 , pp. 1011-1020
    • Carter, J.S.1
  • 5
    • 0033288941 scopus 로고    scopus 로고
    • Selective Inhibitors of Cyclooxygenase-2 (COX-2)
    • Talley, J. J. Selective Inhibitors of Cyclooxygenase-2 (COX-2). Prog. Med. Chem. 1999, 36, 201-234.
    • (1999) Prog. Med. Chem. , vol.36 , pp. 201-234
    • Talley, J.J.1
  • 6
    • 0025754779 scopus 로고
    • Expressions of a mitogen-responsive gene encoding prostaglandin synthase regulated by mRNA splicing
    • Xie, W.; Chipman, J. G.; Robertson, D. L.; Erikson, R. L.; Simmons, D. L. Expressions of a mitogen-responsive gene encoding prostaglandin synthase regulated by mRNA splicing. Proc. Natl. Acad. Sci. U. S. A. 1991, 88, 2692-2696.
    • (1991) Proc. Natl. Acad. Sci. U. S. A. , vol.88 , pp. 2692-2696
    • Xie, W.1    Chipman, J.G.2    Robertson, D.L.3    Erikson, R.L.4    Simmons, D.L.5
  • 7
    • 0025871150 scopus 로고
    • TISIO a Phorbol Ester Tumor Promoter-Inducible mRNA from Swiss 3T3 Cells, Encodes a Novel Prostaglandin Synthase/Cyclooxygenase Homolog
    • Kujubu, D. A.; Fletcher, B. S.; Varnum, B. C.; Lim, R. W.; Herschman, H. R. TISIO, a Phorbol Ester Tumor Promoter-Inducible mRNA from Swiss 3T3 Cells, Encodes a Novel Prostaglandin Synthase/Cyclooxygenase Homolog. J. Biol. Chem. 1991, 266, 12866-12872.
    • (1991) J. Biol. Chem. , vol.266 , pp. 12866-12872
    • Kujubu, D.A.1    Fletcher, B.S.2    Varnum, B.C.3    Lim, R.W.4    Herschman, H.R.5
  • 9
    • 0036156424 scopus 로고    scopus 로고
    • Cyclooxygenase-2 10 Years Later
    • Hinz, B.; Brune, K. Cyclooxygenase-2 10 Years Later. J. Pharm. Exp. Therap. 2002, 300, 367-375.
    • (2002) J. Pharm. Exp. Therap. , vol.300 , pp. 367-375
    • Hinz, B.1    Brune, K.2
  • 10
    • 0032916736 scopus 로고    scopus 로고
    • COX-2 Selective Inhibitors: The New Super Aspirins
    • DeWitt, D. L. COX-2 Selective Inhibitors: the New Super Aspirins. Mol. Pharmacol. 1999, 55, 625-631.
    • (1999) Mol. Pharmacol. , vol.55 , pp. 625-631
    • DeWitt, D.L.1
  • 11
    • 0027146692 scopus 로고
    • Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase
    • Mitchell, J. A.; Akarasereenont, P.; Thiemermann, C.; Flower, R. J.; Vane, J. R. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11693-11697.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 11693-11697
    • Mitchell, J.A.1    Akarasereenont, P.2    Thiemermann, C.3    Flower, R.J.4    Vane, J.R.5
  • 12
    • 0002281945 scopus 로고
    • NSAID Gastropathy Epidemiology
    • Fries, J. F. NSAID Gastropathy: Epidemiology. J. Musculoskeletal Med. 1991, 8, 21-28.
    • (1991) J. Musculoskeletal Med. , vol.8 , pp. 21-28
    • Fries, J.F.1
  • 13
    • 0001650323 scopus 로고
    • Selective Cyclooxygenase Inhibitors
    • For a review, see: Reitz, D. B.; Seibert, K. Selective Cyclooxygenase Inhibitors. Annu. Rep. Med. Chem. 1995, 30, 179-188.
    • (1995) Annu. Rep. Med. Chem. , vol.30 , pp. 179-188
    • Reitz, D.B.1    Seibert, K.2
  • 14
    • 77956739670 scopus 로고    scopus 로고
    • Selective Cyclooxygenase-2 Inhibitors
    • For a review, see: Prasit, P.; Riendeau, D. Selective Cyclooxygenase-2 Inhibitors. Annu. Rep. Med. Chem. 1997, 32, 211-220.
    • (1997) Annu. Rep. Med. Chem. , vol.32 , pp. 211-220
    • Prasit, P.1    Riendeau, D.2
  • 17
    • 0033761126 scopus 로고    scopus 로고
    • Cyclooxygenase-2 Inhibition and Side-effects of Nonsteroidal Antiinflammatory Drugs in Gastrointestinal Tract
    • (a) Meyer-Kirchrath, J.; Schror, K. Cyclooxygenase-2 Inhibition and Side-effects of Nonsteroidal Antiinflammatory Drugs in Gastrointestinal Tract. Curr. Med. Chem. 2000, 7, 1121-1129.
    • (2000) Curr. Med. Chem. , vol.7 , pp. 1121-1129
    • Meyer-Kirchrath, J.1    Schror, K.2
  • 18
    • 0035910976 scopus 로고    scopus 로고
    • Cyclooxygenase inhibitors and thrombogenicity
    • (b) Catella-Lawson, F.; Crofford, L. J. Cyclooxygenase inhibitors and thrombogenicity. Am. J. Med. 2001, 110, 28S-32S.
    • (2001) Am. J. Med. , vol.110
    • Catella-Lawson, F.1    Crofford, L.J.2
  • 19
    • 0035934070 scopus 로고    scopus 로고
    • Risk of Cardiovascular Events Associated with Selective COX-2 Inhibitors
    • Mukherjee, D.; Nissen, S. E.; Topol, E. J. Risk of Cardiovascular Events Associated with Selective COX-2 Inhibitors. JAMA. 2001, 286, 954-959.
    • (2001) JAMA , vol.286 , pp. 954-959
    • Mukherjee, D.1    Nissen, S.E.2    Topol, E.J.3
  • 20
    • 0033031331 scopus 로고    scopus 로고
    • COX-2 Inhibitors
    • Hawkey, C. J. COX-2 Inhibitors. Lancet. 1999, 353, 307-314.
    • (1999) Lancet , vol.353 , pp. 307-314
    • Hawkey, C.J.1
  • 21
    • 0033577982 scopus 로고    scopus 로고
    • Gastrointestinal Toxicity of Non Steroidal Antiinflammatory Drugs
    • (a) Wolfe, M. M.; Lichtenstein, D. R.; Singh, G. Gastrointestinal Toxicity of Non Steroidal Antiinflammatory 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
  • 22
    • 0037151919 scopus 로고    scopus 로고
    • Efficacy, tolerability, and upper gastrointestinal safety of celecoxib for treatment of osteoarthritis and rheumatoid arthritis: Systematic review of randomized controlled trials
    • (b) Deeks, J. J.; Smith, L. A.; Bradley, M. D. Efficacy, tolerability, and upper gastrointestinal safety of celecoxib for treatment of osteoarthritis and rheumatoid arthritis: systematic review of randomized controlled trials. Br. Med. J. 2002, 325, 619-627.
    • (2002) Br. Med. J. , vol.325 , pp. 619-627
    • Deeks, J.J.1    Smith, L.A.2    Bradley, M.D.3
  • 23
    • 0028182409 scopus 로고
    • Novel Nonsteroidal Antiinflammatory Drug Derivatives with Markedly Reduced Ulcerogenic Properties in Rats
    • Wallace, J. L.; Reuter, B.; Cicala, C.; McKnight, W.; Cirino, G.; Gisham, M. B. Novel Nonsteroidal Antiinflammatory Drug Derivatives with Markedly Reduced Ulcerogenic Properties in Rats. Gastroenterology 1994, 107, 173-179.
    • (1994) Gastroenterology , vol.107 , pp. 173-179
    • Wallace, J.L.1    Reuter, B.2    Cicala, C.3    McKnight, W.4    Cirino, G.5    Gisham, M.B.6
  • 25
    • 0029100370 scopus 로고
    • A Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drug Accelerates Gastric Ulcer Healing in Rats
    • Elliott, S. N.; McKnight, W.; Cirino, G.; Wallace, J. L. A Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drug Accelerates Gastric Ulcer Healing in Rats. Gastroenterology 1995, 109, 524-530.
    • (1995) Gastroenterology , vol.109 , pp. 524-530
    • Elliott, S.N.1    McKnight, W.2    Cirino, G.3    Wallace, J.L.4
  • 26
    • 0008915459 scopus 로고    scopus 로고
    • Effects of a Nitric Oxide-Releasing Naproxen Derivative on Hypertension and Gastric Damage Induced by Chronic Nitric Oxide Inhibition in the Rat
    • Muscara, M. N.; McNight, W.; Del Soldato, P.; Wallace, J. L. Effects of a Nitric Oxide-Releasing Naproxen Derivative on Hypertension and Gastric Damage Induced by Chronic Nitric Oxide Inhibition in the Rat. Pharmacol. Lett. 1998, 62, 235-240.
    • (1998) Pharmacol. Lett. , vol.62 , pp. 235-240
    • Muscara, M.N.1    McNight, W.2    Del Soldato, P.3    Wallace, J.L.4
  • 27
    • 0003122433 scopus 로고
    • Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drugs: Novel Approach for Reducing Gastrointestinal Toxicity
    • (a) Wallace, J. L.; Reuter, B.; Cirino, G. Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drugs: Novel Approach for Reducing Gastrointestinal Toxicity. J. Gastroenterol. Hepatol. 1994, 9, S40-S44.
    • (1994) J. Gastroenterol. Hepatol. , vol.9
    • Wallace, J.L.1    Reuter, B.2    Cirino, G.3
  • 28
    • 0036805497 scopus 로고    scopus 로고
    • NO-Donors (VII [I]): Synthesis and Cyclooxygenase Inhibitory Properties of N- and S-Nitrooxypivaloyl-cysteine Derivatives of Naproxen - A Novel Type of No-NSAID
    • (b) Kartasasmita, R. E.; Laufer, S.; Lehmann, J. NO-Donors (VII [I]): Synthesis and Cyclooxygenase Inhibitory Properties of N- and S-Nitrooxypivaloyl-cysteine Derivatives of Naproxen - A Novel Type of No-NSAID. Arch. Pharm. Pharm. Med. Chem. 2002, 335, 363-366.
    • (2002) Arch. Pharm. Pharm. Med. Chem. , vol.335 , pp. 363-366
    • Kartasasmita, R.E.1    Laufer, S.2    Lehmann, J.3
  • 29
    • 0035352883 scopus 로고    scopus 로고
    • Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drugs: Novel Gastrointestinal Sparing Drugs
    • Bandarage, U. K.; Janero, D. R.; Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drugs: Novel Gastrointestinal Sparing Drugs. Mini-Rev. Med. Chem. 2000, 1, 57-70.
    • (2000) Mini-Rev. Med. Chem. , vol.1 , pp. 57-70
    • Bandarage, U.K.1    Janero, D.R.2
  • 33
    • 0032554683 scopus 로고    scopus 로고
    • Inhaled Nitric Oxide Inhibits Human Platelet Aggregation, P-Selectin Expression, and Fibrinogen Binding In Vitro and In Vivo
    • Gries, A.; Bode, C.; Peter, K.; Herr, A.; Böhrer, H.; Motsch, J.; Martin, E. Inhaled Nitric Oxide Inhibits Human Platelet Aggregation, P-Selectin Expression, and Fibrinogen Binding In Vitro and In Vivo. Circulation 1998, 97, 1481-1487.
    • (1998) Circulation , vol.97 , pp. 1481-1487
    • Gries, A.1    Bode, C.2    Peter, K.3    Herr, A.4    Böhrer, H.5    Motsch, J.6    Martin, E.7
  • 34
    • 0030710245 scopus 로고    scopus 로고
    • Nitric Oxide Inhalation Inhibits Platelet Aggregation and Platelet-Mediated Pulmonary Thrombosis in Rats
    • Nong, Z.; Hoylaerts, M.; Pelt, N. V.; Collen, D.; Janssens, S. Nitric Oxide Inhalation Inhibits Platelet Aggregation and Platelet-Mediated Pulmonary Thrombosis in Rats. Circ. Res. 1997, 81, 865-869.
    • (1997) Circ. Res. , vol.81 , pp. 865-869
    • Nong, Z.1    Hoylaerts, M.2    Pelt, N.V.3    Collen, D.4    Janssens, S.5
  • 37
    • 0035838850 scopus 로고    scopus 로고
    • Hydroboration. 97. Synthesis of New Exceptional Chloroborane-Lewis Base Adducts for Hydroboration. Dioxane-Monochloroborane as a Superior Reagent for the Selective Hydroboration of Terminal Alkenes
    • Kanth, J. V. B.; Brown, H. C. Hydroboration. 97. Synthesis of New Exceptional Chloroborane-Lewis Base Adducts for Hydroboration. Dioxane-Monochloroborane as a Superior Reagent for the Selective Hydroboration of Terminal Alkenes. J. Org. Chem. 2001, 66, 5359-5365.
    • (2001) J. Org. Chem. , vol.66 , pp. 5359-5365
    • Kanth, J.V.B.1    Brown, H.C.2
  • 38
    • 0035847261 scopus 로고    scopus 로고
    • Bone Collagen Cross Links: A Convergent Synthesis of (+)-Deoxypyrrolidine
    • Adamczyk, M.; Johnson, D. D.; Reddy, R. E. Bone Collagen Cross Links: A Convergent Synthesis of (+)-Deoxypyrrolidine. J. Org. Chem. 2001, 66, 11-19.
    • (2001) J. Org. Chem. , vol.66 , pp. 11-19
    • Adamczyk, M.1    Johnson, D.D.2    Reddy, R.E.3
  • 40
    • 0028327029 scopus 로고
    • A Remarkable Substituent Effect on the Enantioselectivity of Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols: A New Enantiocontrolled Synthesis of (-)-Debromoaplysin and (-)-Aplysin
    • Nemoto, H.; Nagamochi, M.; Ishibashi, H.; Fukumoto, K. A Remarkable Substituent Effect on the Enantioselectivity of Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols: A New Enantiocontrolled Synthesis of (-)-Debromoaplysin and (-)-Aplysin. J. Org. Chem. 1994, 59, 74-79.
    • (1994) J. Org. Chem. , vol.59 , pp. 74-79
    • Nemoto, H.1    Nagamochi, M.2    Ishibashi, H.3    Fukumoto, K.4
  • 41
    • 0000878032 scopus 로고    scopus 로고
    • A Mild Efficient, Inexpensive, and Selective Cleavage of Primary tert-Butyldimethylsilyl Ethers by Oxone in Aqueous Methanol
    • Sabitha, G.; Syamala, M.; Yadav, J. S. A Mild, Efficient, Inexpensive, and Selective Cleavage of Primary tert-Butyldimethylsilyl Ethers by Oxone in Aqueous Methanol. Org. Lett. 1999, 1, 1701-1703.
    • (1999) Org. Lett. , vol.1 , pp. 1701-1703
    • Sabitha, G.1    Syamala, M.2    Yadav, J.S.3
  • 42
    • 0036525943 scopus 로고    scopus 로고
    • Nitric Oxide Donors: Chemical Activities and Biological Applications
    • Wang, P. G.; Xian, M.; Tang, X.; Wu, X.; Wen, Z.; Cai, T.; Janczuk, J. Nitric Oxide Donors: Chemical Activities and Biological Applications. Chem. Rev. 2002, 102, 1091-1134.
    • (2002) Chem. Rev. , vol.102 , pp. 1091-1134
    • Wang, P.G.1    Xian, M.2    Tang, X.3    Wu, X.4    Wen, Z.5    Cai, T.6    Janczuk, J.7
  • 43
    • 0025333221 scopus 로고
    • Cyclohexane Diester Analogues of Phorbol Ester as Potential Activators of Protein Kinase C
    • Kerr, D. E.; Kissinger, L. F.; Shoyab, M. Cyclohexane Diester Analogues of Phorbol Ester as Potential Activators of Protein Kinase C. J. Med. Chem. 1990, 33, 1958-1962.
    • (1990) J. Med. Chem. , vol.33 , pp. 1958-1962
    • Kerr, D.E.1    Kissinger, L.F.2    Shoyab, M.3
  • 44
    • 0036166882 scopus 로고    scopus 로고
    • In situ Alcohol Oxidation-Wittig Reactions Using Non-Stabilized Phosphoranes
    • Blackburn, L.; Pei, C.; Taylor, R. J. K. In situ Alcohol Oxidation-Wittig Reactions Using Non-Stabilized Phosphoranes. Syn Lett. 2002, 2, 215-218.
    • (2002) Syn. Lett. , vol.2 , pp. 215-218
    • Blackburn, L.1    Pei, C.2    Taylor, R.J.K.3
  • 45
    • 1842633137 scopus 로고    scopus 로고
    • 2-Fluorobenzenesulfonyl Compounds for the Treatment of Inflammation, WO 01/81332, 2001
    • Brown, D. L.; Graneto, M. J.; Ludwig, C. L.; Talley, J. J. 2-Fluorobenzenesulfonyl Compounds for the Treatment of Inflammation, WO 01/81332, 2001.
    • Brown, D.L.1    Graneto, M.J.2    Ludwig, C.L.3    Talley, J.J.4
  • 46
    • 0029953233 scopus 로고    scopus 로고
    • Human Whole Blood Assays for Inhibition of Prostaglandin G/H Synthases-1 and -2 Using A23187 and Lipopolysaccharide Stimulation of Thromboxane B2 Production
    • Young, J. M.; Panah, S.; Satchawatcharaphong, C.; Cheung, P. S. Human Whole Blood Assays for Inhibition of Prostaglandin G/H Synthases-1 and -2 Using A23187 and Lipopolysaccharide Stimulation of Thromboxane B2 Production. Inflamm. Res. 1996, 45, 246-253.
    • (1996) Inflamm. Res. , vol.45 , pp. 246-253
    • Young, J.M.1    Panah, S.2    Satchawatcharaphong, C.3    Cheung, P.S.4
  • 49
    • 0022486177 scopus 로고
    • Studies of Eicosanoid Production in the Air Pouch Model of Synovial Inflammation
    • (a) Sedgwick, A. D.; Lees, P. Studies of Eicosanoid Production in the Air Pouch Model of Synovial Inflammation. Agents Actions, 1986, 18, 429-438.
    • (1986) Agents Actions , vol.18 , pp. 429-438
    • Sedgwick, A.D.1    Lees, P.2


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