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Volumn 60, Issue 8, 2010, Pages 497-505

Synthesis of 1,5-diarylpyrazol-3-propanoic acids towards inhibition of cyclooxygenase-1/2 activity and 5-lipoxygenase-mediated LTB4 formation

Author keywords

Aryl propanoic acids; COX 1 2 inhibitors; Leukotriene B4; Pyrazole

Indexed keywords

ARACHIDONATE 5 LIPOXYGENASE; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2 INHIBITOR; INDOMETACIN; LEUKOTRIENE B4; PROPIONIC ACID DERIVATIVE; ROFECOXIB; CYCLOOXYGENASE 2; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LIPOXYGENASE INHIBITOR; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRAZOLE DERIVATIVE;

EID: 77956371766     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296318     Document Type: Article
Times cited : (16)

References (32)
  • 1
    • 0037180757 scopus 로고    scopus 로고
    • Inflammation and cancer
    • Coussens LM, Werb Z. Inflammation and cancer . Nature. 2002;420:860-7.
    • (2002) Nature , vol.420 , pp. 860-867
    • Coussens, L.M.1    Werb, Z.2
  • 2
    • 0037180812 scopus 로고    scopus 로고
    • Points of control in inflammation
    • Nathan C. Points of control in inflammation. Nature. 2002; 420:846-52.
    • (2002) Nature , vol.420 , pp. 846-852
    • Nathan, C.1
  • 3
    • 0142093151 scopus 로고    scopus 로고
    • 5-Lipoxygenase and atherosclerosis
    • Mehrabian M, Allayee H. 5-Lipoxygenase and atherosclerosis. Curr Opin Lipidol. 2003;14:447-57.
    • (2003) Curr Opin Lipidol , vol.14 , pp. 447-457
    • Mehrabian, M.1    Allayee, H.2
  • 4
    • 0020597565 scopus 로고
    • Leukotrienes: Mediators of immediate hypersensitivity reactions and inflammation
    • Samuelsson B. Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation. Science 1983; 220:568-75. (Pubitemid 13130140)
    • (1983) Science , vol.220 , Issue.4597 , pp. 568-575
    • Samuelsson, B.1
  • 5
    • 0026969308 scopus 로고
    • Prostaglandins as modulators rather than mediators of inflammation
    • Weissmann G. Prostaglandins as modulators rather than mediators of inflammation. J Lipid Mediat. 1993;6:275-86. (Pubitemid 23152460)
    • (1992) Journal of Lipid Mediators , vol.6 , Issue.1-3 , pp. 275-286
    • Weissmann, G.1
  • 6
    • 1342315146 scopus 로고    scopus 로고
    • Lipoxygenase and cyclooxygenase metabolism: New insights in treatment and chemoprevention of pancreatic cancer
    • DOI 10.1186/1476-4598-2-10
    • Ding XZ, Hennig R, Adrian TE. Lipoxygenase and cyclooxygenase metabolism: new insights in treatment and chemoprevention of pancreatic cancer . Mol Cancer. 2003; 2:10. (Pubitemid 38751487)
    • (2003) Molecular Cancer , vol.2 , pp. 10
    • Ding, X.-Z.1    Hennig, R.2    Adrian, T.E.3
  • 7
    • 0242611540 scopus 로고    scopus 로고
    • Cyclooxygenase-2 and 5-lipoxygenase converging functions on cell proliferation and tumor angiogenesis: Implications for cancer therapy
    • DOI 10.1096/fj.03-0053rev
    • Romano M, Claria J. Cyclooxygenase-2 and 5-lipoxygenase converging functions on cell proliferation and tumor angiogenesis: implications for cancer therapy . Faseb J. 2003; 17:1986-95. (Pubitemid 37392443)
    • (2003) FASEB Journal , vol.17 , Issue.14 , pp. 1986-1995
    • Romano, M.1    Claria, J.2
  • 8
    • 33750102847 scopus 로고    scopus 로고
    • Therapeutic options for 5-lipoxygenase inhibitors
    • Werz O, Steinhilber D. Therapeutic options for 5-lipoxygenase inhibitors. Pharmacol Ther. 2006;112:701-18.
    • (2006) Pharmacol Ther , vol.112 , pp. 701-718
    • Werz, O.1    Steinhilber, D.2
  • 9
    • 23844530173 scopus 로고    scopus 로고
    • Leukotriene modifiers as potential therapeutics for cardiovascular disease
    • Funk CD. Leukotriene modifiers as potential therapeutics for cardiovascular disease . Nat Rev Drug Discov. 2005;4: 664-72.
    • (2005) Nat Rev Drug Discov , vol.4 , pp. 664-672
    • Funk, C.D.1
  • 10
    • 0042574211 scopus 로고    scopus 로고
    • Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs
    • DOI 10.1016/S0223-5234(03)00115-6
    • Charlier C, Michaux C. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs . Eur J Med Chem. 2003;38:645-59. (Pubitemid 36980661)
    • (2003) European Journal of Medicinal Chemistry , vol.38 , Issue.7-8 , pp. 645-659
    • Charlier, C.1    Michaux, C.2
  • 13
    • 72249110442 scopus 로고    scopus 로고
    • Further studies on arylpiperazinyl alkyl pyridazinones: Discovery of an exceptionally potent, orally active, antinociceptive agent in thermally induced pain
    • Biancalani C, Giovannoni MP, Pieretti S, Cesari N, Graziano A, Vergelli C, et al. Further studies on arylpiperazinyl alkyl pyridazinones: discovery of an exceptionally potent, orally active, antinociceptive agent in thermally induced pain. J Med Chem. 2009;52:7397-409.
    • (2009) J Med Chem , vol.52 , pp. 7397-7409
    • Biancalani, C.1    Giovannoni, M.P.2    Pieretti, S.3    Cesari, N.4    Graziano, A.5    Vergelli, C.6
  • 14
    • 34548071504 scopus 로고    scopus 로고
    • 4-amino-5-substituted-3(2H)-pyridazinones as orally active antinociceptive agents: Synthesis and studies on the mechanism of action
    • Giovannoni MP, Cesari N, Vergelli C, Graziano A, Biancalani C, Biagini P, et al. 4-amino-5-substituted-3(2H)-pyridazinones as orally active antinociceptive agents: synthesis and studies on the mechanism of action. J Med Chem. 2007;50:3945-53.
    • (2007) J Med Chem , vol.50 , pp. 3945-3953
    • Giovannoni, M.P.1    Cesari, N.2    Vergelli, C.3    Graziano, A.4    Biancalani, C.5    Biagini, P.6
  • 15
    • 0042736107 scopus 로고    scopus 로고
    • Amide derivatives of [5-chloro-6-(2-chloro/fluorobenzoyl)- 2-benzoxazolinone-3-yl]acetic acids as potential analgesic and anti-inflammatory compounds
    • Banoglu E, Okcelik B, Kupeli E, Unlu S, Yesilada E, Amat M, et al. Amide derivatives of [5-chloro-6-(2-chloro/fluorobenzoyl)- 2-benzoxazolinone-3-yl] acetic acids as potential analgesic and anti-inflammatory compounds . Arch Pharm (Weinheim). 2003;336:251-7.
    • (2003) Arch Pharm (Weinheim) , vol.336 , pp. 251-257
    • Banoglu, E.1    Okcelik, B.2    Kupeli, E.3    Unlu, S.4    Yesilada, E.5    Amat, M.6
  • 16
    • 1242314379 scopus 로고    scopus 로고
    • Amide derivatives of [6-(5-methyl-3-phenylpyrazole- 1-yl)-3(2H)- pyridazinone-2-yl]acetic acids as potential analgesic and anti-inflammatory compounds
    • Banoglu E, Akoglu C, Unlu S, Kupeli E, Yesilada E, Sahin MF. Amide derivatives of [6-(5-methyl-3-phenylpyrazole- 1-yl)-3(2H)-pyridazinone-2-yl] acetic acids as potential analgesic and anti-inflammatory compounds . Arch Pharm (Weinheim). 2004;337:7-14.
    • (2004) Arch Pharm (Weinheim) , vol.337 , pp. 7-14
    • Banoglu, E.1    Akoglu, C.2    Unlu, S.3    Kupeli, E.4    Yesilada, E.5    Sahin, M.F.6
  • 17
    • 25444467216 scopus 로고    scopus 로고
    • Synthesis of amide derivatives of [6-(3,5-dimethylpyrazol- 1-yl)-3(2H)-pyridazinone-2-yl] acetic acid and their analgesic and anti-inflammatory properties
    • Banoglu E, Akoglu C, Unlu S, Ergun BC, Kupeli E, Yesilada E, et al. Synthesis of amide derivatives of [6-(3,5-dimethylpyrazol- 1-yl)-3(2H)- pyridazinone-2-yl] acetic acid and their analgesic and anti-inflammatory properties . Arzneimittelforschung. 2005;55(9):520-7.
    • (2005) Arzneimittelforschung , vol.55 , Issue.9 , pp. 520-527
    • Banoglu, E.1    Akoglu, C.2    Unlu, S.3    Ergun, B.C.4    Kupeli, E.5    Yesilada, E.6
  • 18
    • 37549052892 scopus 로고    scopus 로고
    • Synthesis of the amide derivatives of 3-[1-(3-pyridazinyl)- 5-phenyl-1H-pyrazole-3-yl]propanoic acids as potential analgesic compounds
    • Banoglu E, Sukuroglu M, Çalişkan Ergün B, Nacak Baytas S, Aypar E, Ark M. Synthesis of the amide derivatives of 3-[1-(3-pyridazinyl)- 5-phenyl-1H-pyrazole-3-yl]propanoic acids as potential analgesic compounds . Turkish J Chem. 2007;31:677-87.
    • (2007) Turkish J Chem , vol.31 , pp. 677-687
    • Banoglu, E.1    Sukuroglu, M.2    Çalişkan Ergün, B.3    Nacak Baytas, S.4    Aypar, E.5    Ark, M.6
  • 19
    • 34547745581 scopus 로고    scopus 로고
    • Synthesis, characterization and preliminary screening of regioisomeric 1-(3-pyridazinyl)-3-arylpyrazole and 1-(3- Pyridazinyl)-5-arylpyrazole derivatives towards cyclooxygenase inhibition
    • Unlu S, Banoglu E, Ito S, Niiya T, Eren G, Okcelik B, et al. Synthesis, characterization and preliminary screening of regioisomeric 1-(3-pyridazinyl)-3- arylpyrazole and 1-(3- pyridazinyl)-5-arylpyrazole derivatives towards cyclooxygenase inhibition. J Enzyme Inhib Med Chem. 2007;22: 351-61.
    • (2007) J Enzyme Inhib Med Chem , vol.22 , pp. 351-361
    • Unlu, S.1    Banoglu, E.2    Ito, S.3    Niiya, T.4    Eren, G.5    Okcelik, B.6
  • 20
    • 84981833437 scopus 로고
    • Chemotherapeutic studies in the heterocyclic series. IV. Pyridazines. 1. Cyclic maleic and citraconic hydrazides
    • Druey J, Meier K, Eichenberger K. Chemotherapeutic studies in the heterocyclic series. IV. Pyridazines. 1. Cyclic maleic and citraconic hydrazides . Helv Chim. Acta. 1954; 37:121-33.
    • (1954) Helv Chim. Acta , Issue.37 , pp. 121-133
    • Druey, J.1    Meier, K.2    Eichenberger, K.3
  • 21
    • 77956356522 scopus 로고    scopus 로고
    • Process for preparing 1,5-diaryl-3-substituted pyrazoles
    • US 6384233
    • Abdel-magid AF, Harris BD, Maryanoff CA. Process for preparing 1,5-diaryl-3-substituted pyrazoles . US 6384233. 2002.
    • (2002)
    • Abdel-magid, A.F.1    Harris, B.D.2    Maryanoff, C.A.3
  • 22
    • 0012780458 scopus 로고
    • Synthesis and properties of aryl-1,3-dioxo carboxylic acids
    • Murray W, Watcher MP. Synthesis and properties of aryl-1,3-dioxo carboxylic acids . J Org Chem. 1990;55:3424-26.
    • (1990) J Org Chem , vol.55 , pp. 3424-3426
    • Murray, W.1    Watcher, M.P.2
  • 23
    • 77956391224 scopus 로고
    • Regioselective synthesis of 1,5-disubstituted pyrazoles
    • EP0293221
    • Murray W, Wachter MP. Regioselective synthesis of 1,5-disubstituted pyrazoles . EP0293221. 1988.
    • (1988)
    • Murray, W.1    Wachter, M.P.2
  • 24
    • 0027325985 scopus 로고
    • The mechanism of formation of 6-aryl-4,6-dioxohexanoic acids from aryl ketones and succinic acids
    • Murray W, Lalan P, Connolly PJ. The mechanism of formation of 6-aryl-4,6-dioxohexanoic acids from aryl ketones and succinic acids . Tetrahedron Lett. 1993;34:5189-92.
    • (1993) Tetrahedron Lett , vol.34 , pp. 5189-5192
    • Murray, W.1    Lalan, P.2    Connolly, P.J.3
  • 25
    • 77956370342 scopus 로고
    • Pharmacologically active 1,5-diaryl- 3-substitutedpyrazoles and method for synthesizing the same
    • EP0248594
    • Wachter MP, Ferro MP. Pharmacologically active 1,5-diaryl- 3-substitutedpyrazoles and method for synthesizing the same. EP0248594. 1987.
    • (1987)
    • Wachter, M.P.1    Ferro, M.P.2
  • 26
    • 77956385172 scopus 로고
    • Pharmacologically active N-1 and C-5 heterocyclic pyrazoles and method for synthesizing the same
    • US 5242940
    • Wachter MP, Murray WV. Pharmacologically active N-1 and C-5 heterocyclic pyrazoles and method for synthesizing the same. US 5242940 . 1993.
    • (1993)
    • Wachter, M.P.1    Murray, W.V.2
  • 27
    • 0028089109 scopus 로고
    • NS-398, a new anti-inflammatory agent, selectively inhibits prostaglandin G/H synthase/cyclooxygenase (COX-2) activity in vitro
    • DOI 10.1016/0090-6980(94)90074-4
    • Futaki N, Takahashi S, Yokoyama M, Arai I, Higuchi S, Otomo S. NS-398, a new anti-inflammatory agent, selectively inhibits prostaglandin G/H synthase/cyclooxygenase (COX-2) activity in vitro . Prostaglandins. 1994;47:55-9. (Pubitemid 24053843)
    • (1994) Prostaglandins , vol.47 , Issue.1 , pp. 55-59
    • Futaki, N.1    Takahashi, S.2    Yokoyama, M.3    Arai, I.4    Higuchi, S.5    Otomo, S.6
  • 28
    • 15444344804 scopus 로고    scopus 로고
    • New cyclooxygenase-2/5-lipoxygenase inhibitors. 1. 7- Tert-Buty1-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: Discovery and variation of the 5-keto substituent
    • Janusz JM, Young PA, Ridgeway JM, Scherz MW, Enzweiler K, Wu LI, et al. New cyclooxygenase-2/5-lipoxygenase inhibitors. 1. 7- tert-Buty1-2,3-dihydro-3, 3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: discovery and variation of the 5-keto substituent . J Med Chem. 1998;41:1112-23.
    • (1998) J Med Chem , vol.41 , pp. 1112-1123
    • Janusz, J.M.1    Young, P.A.2    Ridgeway, J.M.3    Scherz, M.W.4    Enzweiler, K.5    Wu, L.I.6
  • 30
    • 0026101780 scopus 로고
    • The regio-selective synthesis of tepoxalin, 3-[5-(4-chlorophenyl)-1-(4- metoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-methylpropanamide and related 1,5-diarylpyrazole anti-inflammatory agents
    • Murray W, Wachter M, Barton D, Forero-Kelly Y. The regio-selective synthesis of tepoxalin, 3-[5-(4-chlorophenyl)-1-(4-metoxyphenyl)-3-pyrazolyl]-N- hydroxy-N-methylpropanamide and related 1,5-diarylpyrazole anti-inflammatory agents. Synthesis. 1991:18-20.
    • (1991) Synthesis , pp. 18-20
    • Murray, W.1    Wachter, M.2    Barton, D.3    Forero-Kelly, Y.4
  • 32
    • 0033760250 scopus 로고    scopus 로고
    • Structural approaches to explain the selectivity of COX-2 inhibitors: Is there a common pharmacophore?
    • Dannhardt G, Laufer S. Structural approaches to explain the selectivity of COX-2 inhibitors: is there a common pharmacophore? Curr Med Chem. 2000;7:1101-12.
    • (2000) Curr Med Chem , vol.7 , pp. 1101-1112
    • Dannhardt, G.1    Laufer, S.2


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