메뉴 건너뛰기




Volumn 49, Issue 12, 2006, Pages 3659-3666

Structure-activity relationship studies on a series of novel, substituted 1-benzyl-5-phenyltetrazole P2X7 antagonists

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYL 5 PHENYLTETRAZOLE DERIVATIVE; 3 [5 (2,3 DICHLOROPHENYL)TETRAZOL 1 YLMETHYL]PYRIDINE; INTERLEUKIN 1BETA; PURINE P2X7 RECEPTOR; PURINERGIC RECEPTOR BLOCKING AGENT; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33745142545     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm051202e     Document Type: Article
Times cited : (224)

References (51)
  • 2
    • 0031754497 scopus 로고    scopus 로고
    • Receptors for purines and pyrimidines
    • Ralevic, V.; Burnstock, G. Receptors for purines and pyrimidines. Pharmacol. Rev. 1998, 50, 413-492.
    • (1998) Pharmacol. Rev. , vol.50 , pp. 413-492
    • Ralevic, V.1    Burnstock, G.2
  • 3
    • 0037068428 scopus 로고    scopus 로고
    • Purine and pyrimidine (P2) receptors as drug targets
    • Jacobsen, K. A.; Jarvis, M. F.; Williams, M. Purine and pyrimidine (P2) receptors as drug targets. J. Med. Chem. 2002, 45, 4057-4093.
    • (2002) J. Med. Chem. , vol.45 , pp. 4057-4093
    • Jacobsen, K.A.1    Jarvis, M.F.2    Williams, M.3
  • 4
    • 0036788971 scopus 로고    scopus 로고
    • Molecular physiology of P2X receptors
    • North, R. A. Molecular physiology of P2X receptors. Physiol. Rev. 2002, 82, 1013-1067.
    • (2002) Physiol. Rev. , vol.82 , pp. 1013-1067
    • North, R.A.1
  • 5
    • 0029741183 scopus 로고    scopus 로고
    • Numbering of cloned P2 receptors
    • Burnstock, G.; King, B. F. Numbering of cloned P2 receptors. Drug Dev. Res. 1996, 38, 67-71.
    • (1996) Drug Dev. Res. , vol.38 , pp. 67-71
    • Burnstock, G.1    King, B.F.2
  • 6
    • 0029665112 scopus 로고    scopus 로고
    • The cytolytic P2Z receptor for extracellular ATP identified as a P2X (P2X7) receptor
    • Surprenant A.; Rassendren, F.; Kawashima, E.; North, R. A.; Buell, G. The cytolytic P2Z receptor for extracellular ATP identified as a P2X (P2X7) receptor. Science 1996, 272, 735-738.
    • (1996) Science , vol.272 , pp. 735-738
    • Surprenant, A.1    Rassendren, F.2    Kawashima, E.3    North, R.A.4    Buell, G.5
  • 7
    • 0027077621 scopus 로고
    • A novel pathway for the activation of phospholipase D by P2Z purinergic receptors in BAC1.2F5 macrophages
    • El-Moatassim, C.; Dubyak, G. R. A novel pathway for the activation of phospholipase D by P2Z purinergic receptors in BAC1.2F5 macrophages. J Biol. Chem. 1992, 267, 23664-23673.
    • (1992) J Biol. Chem. , vol.267 , pp. 23664-23673
    • El-Moatassim, C.1    Dubyak, G.R.2
  • 8
    • 0028985997 scopus 로고
    • The purinergic P2Z receptor of human macrophage cells. Characterization and possible physiological roles
    • Falzoni, S.; Munerati, M.; Ferrari, D.; Spisani, S.; Moretti, S.; Di Virgilio, F. The purinergic P2Z receptor of human macrophage cells. Characterization and possible physiological roles. J. Clin. Invest. 1995, 95, 1207-1216.
    • (1995) J. Clin. Invest. , vol.95 , pp. 1207-1216
    • Falzoni, S.1    Munerati, M.2    Ferrari, D.3    Spisani, S.4    Moretti, S.5    Di Virgilio, F.6
  • 11
    • 0035029224 scopus 로고    scopus 로고
    • P2 nucleotide receptors in peripheral nerve trunk
    • (a) Irnich, D.; Burgstahler, R. Grafe, P. P2 nucleotide receptors in peripheral nerve trunk. Drug Dev. Res. 2001,52, 83-88.
    • (2001) Drug Dev. Res. , vol.52 , pp. 83-88
    • Irnich, D.1    Burgstahler, R.2    Grafe, P.3
  • 17
    • 0028175838 scopus 로고
    • Interleukin-1 β maturation and release in response to ATP and nigericin. Evidence that potassium depletion mediated by these agents is a necessary and common feature of their activity
    • Perregaux, D.; Gabel, C. A. Interleukin-1 β maturation and release in response to ATP and nigericin. Evidence that potassium depletion mediated by these agents is a necessary and common feature of their activity. J. Biol. Chem. 1994, 269, 15195-15203.
    • (1994) J. Biol. Chem. , vol.269 , pp. 15195-15203
    • Perregaux, D.1    Gabel, C.A.2
  • 19
    • 1342323323 scopus 로고    scopus 로고
    • Mitogen-activated protein kinase and caspase signaling pathways are required for p2X7 receptor (P2X7R)-induced pore formation in Human THP-1 cells
    • Donnelly-Roberts, D. L.; Namovic, M.; Faltynek, C. R.; Jarvis, M. F. Mitogen-activated protein kinase and caspase signaling pathways are required for p2X7 receptor (P2X7R)-induced pore formation in Human THP-1 cells. J. Pharmacol. Exp. Ther. 2004, 308, 1053-1061.
    • (2004) J. Pharmacol. Exp. Ther. , vol.308 , pp. 1053-1061
    • Donnelly-Roberts, D.L.1    Namovic, M.2    Faltynek, C.R.3    Jarvis, M.F.4
  • 26
    • 1642493590 scopus 로고    scopus 로고
    • P2X7 receptor modulation of β-amyloid- and LPS-induced cytokine secretion from human macrophages and microglia
    • (c) Rampe, D.; Wang, L.; Ringheim, G. E. P2X7 receptor modulation of β-amyloid- and LPS-induced cytokine secretion from human macrophages and microglia. J. Neuroimmunol. 2004, 147, 56-61.
    • (2004) J. Neuroimmunol. , vol.147 , pp. 56-61
    • Rampe, D.1    Wang, L.2    Ringheim, G.E.3
  • 28
    • 33745168051 scopus 로고    scopus 로고
    • The role of astrocytes and microglia in persistent pain
    • (a) Raghavendra, V.; DeLeo, J. A. The role of astrocytes and microglia in persistent pain. Adv. Mol. Cell Biol. 2004, 31, 951-966.
    • (2004) Adv. Mol. Cell Biol. , vol.31 , pp. 951-966
    • Raghavendra, V.1    DeLeo, J.A.2
  • 29
    • 15744390540 scopus 로고    scopus 로고
    • Review: Neuronal-glial interactions in central sensitization
    • (b) Milligan, E. D.; Maier, S. F.; Watkins, L. R. Review: Neuronal-glial interactions in central sensitization. Sem. Pain Med. 2003, 1, 171-183.
    • (2003) Sem. Pain Med. , vol.1 , pp. 171-183
    • Milligan, E.D.1    Maier, S.F.2    Watkins, L.R.3
  • 30
    • 0030913028 scopus 로고    scopus 로고
    • Cytokines, nerve growth factor and inflammatory hyperalgesia: The contribution of tumor necrosis factor alpha
    • Woolf, C. J.; Allchorne, A.; Safieh-Garabedien, B.; Poole, S. Cytokines, nerve growth factor and inflammatory hyperalgesia: The contribution of tumor necrosis factor alpha. Br. J. Pharmacol. 1997, 121, 417-424.
    • (1997) Br. J. Pharmacol. , vol.121 , pp. 417-424
    • Woolf, C.J.1    Allchorne, A.2    Safieh-Garabedien, B.3    Poole, S.4
  • 31
    • 0035252354 scopus 로고    scopus 로고
    • The role of neuroinflammation and neuroimmune activation in persistent pain
    • DeLeo, J. A.; Yezierski, R. P. The role of neuroinflammation and neuroimmune activation in persistent pain. Pain 2001, 90, 1-6.
    • (2001) Pain , vol.90 , pp. 1-6
    • DeLeo, J.A.1    Yezierski, R.P.2
  • 32
    • 0036774263 scopus 로고    scopus 로고
    • Glial cell plasticity in sensory ganglia induced by nerve damage
    • Hanani, M.; Huang, T. Y.; Cherkas, P. S.; Ledda, M.; Pannese, E. Glial cell plasticity in sensory ganglia induced by nerve damage. Neuroscience 2002, 114, 279-283.
    • (2002) Neuroscience , vol.114 , pp. 279-283
    • Hanani, M.1    Huang, T.Y.2    Cherkas, P.S.3    Ledda, M.4    Pannese, E.5
  • 33
    • 0033830198 scopus 로고    scopus 로고
    • Pain: Molecular mechanisms
    • Costigan, M.; Woolf, C. J. Pain: Molecular mechanisms. J. Pain 2000, 1, 35-44.
    • (2000) J. Pain , vol.1 , pp. 35-44
    • Costigan, M.1    Woolf, C.J.2
  • 36
    • 0036899591 scopus 로고    scopus 로고
    • Relief of inflammatory pain in rats by local use of the selective P2X7 ATP receptor inhibitor, oxidized ATP
    • Dell'Antonio, G.; Quattrini, A.; Cin, E. D.; Fulgenzi, A.; Ferrero, M. E. Relief of inflammatory pain in rats by local use of the selective P2X7 ATP receptor inhibitor, oxidized ATP. Arthritis Rheum. 2002, 46, 3378-3385.
    • (2002) Arthritis Rheum. , vol.46 , pp. 3378-3385
    • Dell'Antonio, G.1    Quattrini, A.2    Cin, E.D.3    Fulgenzi, A.4    Ferrero, M.E.5
  • 37
    • 0030977216 scopus 로고    scopus 로고
    • The isoquinoline derivative KN-62 a potent antagonist of the P2Z-receptor of human lymphocytes
    • Gargett, C. E.; Wiley, J. S. The isoquinoline derivative KN-62 a potent antagonist of the P2Z-receptor of human lymphocytes. Br. J. Pharmacol. 1997, 120, 1483-1490.
    • (1997) Br. J. Pharmacol. , vol.120 , pp. 1483-1490
    • Gargett, C.E.1    Wiley, J.S.2
  • 39
    • 0035673858 scopus 로고    scopus 로고
    • 7 receptor antagonists: Tyrosyl derivatives synthesized using a sequential parallel synthetic approach
    • 7 receptor antagonists: Tyrosyl derivatives synthesized using a sequential parallel synthetic approach. Drug Dev. Res. 2001, 54, 75-87.
    • (2001) Drug Dev. Res. , vol.54 , pp. 75-87
    • Ravi, R.G.1    Kertesy, S.B.2    Dubyak, G.R.3    Jacobsen, K.A.4
  • 45
    • 0027135192 scopus 로고
    • A new method for the preparation of tetrazoles from nitriles using trimethylsilylazide/trimethylaluminum
    • Huff, B. E.; Staszak, M. A. A new method for the preparation of tetrazoles from nitriles using trimethylsilylazide/trimethylaluminum. Tetrahedron Lett. 1993, 34, 8011-8014.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8011-8014
    • Huff, B.E.1    Staszak, M.A.2
  • 46
    • 33745134819 scopus 로고    scopus 로고
    • note
    • The regiochemistry of the 1,5- and 2,5-substituted products 8a and 8b was determined from the NOE effect observed for the 1,5-isomer between the benzylic protons and the ortho hydrogen on the adjacent group Ar. No NOE effect was observed for the 2,5-isomer.
  • 47
    • 0001250488 scopus 로고
    • Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole
    • Duncia, J. V.; Pierce, M. E.; Santella, J. B., III. Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole. J. Org. Chem. 1991, 56, 2395-2400.
    • (1991) J. Org. Chem. , vol.56 , pp. 2395-2400
    • Duncia, J.V.1    Pierce, M.E.2    Santella III, J.B.3
  • 48
    • 0034010063 scopus 로고    scopus 로고
    • A comparison of glucose-and glucosamine-related inhibitors: Probing the interaction of the 2-hydroxy group with retaining β-glucosidases
    • Panday, N.; Meyyappan, M.; Vasella, A. A comparison of glucose-and glucosamine-related inhibitors: Probing the interaction of the 2-hydroxy group with retaining β-glucosidases. Helv. Chim. Acta 2000, 83, 513-538.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 513-538
    • Panday, N.1    Meyyappan, M.2    Vasella, A.3
  • 51
    • 33745153538 scopus 로고    scopus 로고
    • note
    • In pharmacokinetic studies, compound 15d was administered at a dose of 10 μmol/kg.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.