메뉴 건너뛰기




Volumn 48, Issue 6, 2005, Pages 1745-1758

(N)-methanocarba 2,N6-disubstituted adenine nucleosides as highly potent and selective A3 adenosine receptor agonists

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE A3 RECEPTOR AGONIST; ADENYLATE CYCLASE; BENZYLAMINE DERIVATIVE; ESTER; FORSKOLIN; RIBOSE;

EID: 15444378502     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049580r     Document Type: Article
Times cited : (98)

References (64)
  • 1
    • 0035209620 scopus 로고    scopus 로고
    • International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors
    • Fredholm, B. B.; IJzerman, A. P.; Jacobson, K. A.; Klotz, K.-N.; Linden, J. International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors. Pharmacol. Rev. 2001, 53, 527-552.
    • (2001) Pharmacol. Rev. , vol.53 , pp. 527-552
    • Fredholm, B.B.1    IJzerman, A.P.2    Jacobson, K.A.3    Klotz, K.-N.4    Linden, J.5
  • 2
    • 0347627795 scopus 로고    scopus 로고
    • Adenosine receptor agonists: From basic medicinal chemistry to clinical development
    • Yao, L.; Burbiel, J. C.; Maass, A.; Müller, C. E. Adenosine receptor agonists: from basic medicinal chemistry to clinical development. Expert Opin. Emerging Drugs 2003, 8, 537-576.
    • (2003) Expert Opin. Emerging Drugs , vol.8 , pp. 537-576
    • Yao, L.1    Burbiel, J.C.2    Maass, A.3    Müller, C.E.4
  • 3
    • 0035924320 scopus 로고    scopus 로고
    • Role of G-protein-coupled adenosine receptors in downregulation of inflammation and protection from tissue damage
    • Ohta, A.; Sitkovsky, M. Role of G-protein-coupled adenosine receptors in downregulation of inflammation and protection from tissue damage. Nature 2001, 414, 916-920.
    • (2001) Nature , vol.414 , pp. 916-920
    • Ohta, A.1    Sitkovsky, M.2
  • 9
    • 2442720039 scopus 로고    scopus 로고
    • 2A adenosine receptor activation improves survival in mouse models of endotoxemia and sepsis
    • 2A adenosine receptor activation improves survival in mouse models of endotoxemia and sepsis. J. Infect. Dis. 2004, 189, 1897-1904.
    • (2004) J. Infect. Dis. , vol.189 , pp. 1897-1904
    • Sullivan, G.W.1    Fang, G.2    Linden, J.3    Scheld, W.M.4
  • 19
    • 0031818111 scopus 로고    scopus 로고
    • Further pharmacological characterization of the adenosine receptor subtype mediating inhibition of oxidative burst in human isolated neutrophils
    • Hannon, J. P.; Bray-French, K. M.; Phillips, R. M.; Fozard, J. R. Further pharmacological characterization of the adenosine receptor subtype mediating inhibition of oxidative burst in human isolated neutrophils. Drug Dev. Res. 1998, 43, 214-224.
    • (1998) Drug Dev. Res. , vol.43 , pp. 214-224
    • Hannon, J.P.1    Bray-French, K.M.2    Phillips, R.M.3    Fozard, J.R.4
  • 23
    • 0035927233 scopus 로고    scopus 로고
    • Ring-constrained (N)methanocarba-nucleosides as adenosine receptor agonists: Independent 5′-uronamide and 2′-deoxy modifications
    • Lee, K.; Ravi, R. G.; Ji, X.-d.; Marquez, V. E.; Jacobson, K. A. Ring-constrained (N)methanocarba-nucleosides as adenosine receptor agonists: Independent 5′-uronamide and 2′-deoxy modifications, Bioorg. Med. Chem. Lett. 2001, 11, 1333-1337.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1333-1337
    • Lee, K.1    Ravi, R.G.2    Ji, X.-D.3    Marquez, V.E.4    Jacobson, K.A.5
  • 28
    • 85077634689 scopus 로고
    • The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products
    • Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981, 1, 1-28.
    • (1981) Synthesis , vol.1 , pp. 1-28
    • Mitsunobu, O.1
  • 30
    • 3342949415 scopus 로고    scopus 로고
    • Preparation of shortened norbelladine analogs
    • Treu, M.; Frohlich, J.; Jordis, U. Preparation of shortened norbelladine analogs. Molecules 2002, 7, 743-750.
    • (2002) Molecules , vol.7 , pp. 743-750
    • Treu, M.1    Frohlich, J.2    Jordis, U.3
  • 31
    • 0011619289 scopus 로고
    • A new synthetic approach to 1-(hydroxymethyl)-8-methoxy-1,2,3,4- tetrahydroisoqyuinolin-4-one
    • Williams, R. M.; Ehrlich, P. P.; Zhai, W.; Hendrix, J. A new synthetic approach to 1-(hydroxymethyl)-8-methoxy-1,2,3,4-tetrahydroisoqyuinolin-4-one. J. Org. Chem. 1989, 52, 2615-2617.
    • (1989) J. Org. Chem. , vol.52 , pp. 2615-2617
    • Williams, R.M.1    Ehrlich, P.P.2    Zhai, W.3    Hendrix, J.4
  • 32
    • 9644285669 scopus 로고
    • A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines
    • Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett. 1975, 4467-4470.
    • (1975) Tetrahedron Lett. , pp. 4467-4470
    • Sonogashira, K.1    Tohda, Y.2    Hagihara, N.3
  • 34
    • 0242267908 scopus 로고    scopus 로고
    • 2-Substitution of adenine nucleotide analogues containing a bicyclo[3.1.0]hexane ring system locked in a Northern conformation: Enhanced potency as P2Y1 receptor antagonists
    • Kim, H. S.; Ohno, M.; Xu, B.; Kim, H. O.; Choi, Y.; Ji, X. D.; Maddileti, S.; Marquez, V. E.; Harden, T. K.; Jacobson, K. A. 2-Substitution of adenine nucleotide analogues containing a bicyclo[3.1.0]hexane ring system locked in a Northern conformation: Enhanced potency as P2Y1 receptor antagonists. J. Med. Chem. 2003, 46, 4974-4987.
    • (2003) J. Med. Chem. , vol.46 , pp. 4974-4987
    • Kim, H.S.1    Ohno, M.2    Xu, B.3    Kim, H.O.4    Choi, Y.5    Ji, X.D.6    Maddileti, S.7    Marquez, V.E.8    Harden, T.K.9    Jacobson, K.A.10
  • 35
    • 0035851341 scopus 로고    scopus 로고
    • Cyclin-dependent kinase (CDK) inhibitors: Development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 1
    • Brun, V.; Legraverend, M.; Grierson, D. S. Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 1. Tetrahedron Lett. 2001, 42, 8161-8164.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8161-8164
    • Brun, V.1    Legraverend, M.2    Grierson, D.S.3
  • 47
    • 0038002076 scopus 로고    scopus 로고
    • 3 adenosine and CB1 receptors activate a PKC-sensitive Cl- Current in human nonpigmented ciliary epithelial cells via a Gβ,γ-coupled MAPK signaling pathway
    • 3 adenosine and CB1 receptors activate a PKC-sensitive Cl- current in human nonpigmented ciliary epithelial cells via a Gβ,γ-coupled MAPK signaling pathway. Br. J. Pharmacol. 2003, 139, 475-486.
    • (2003) Br. J. Pharmacol. , vol.139 , pp. 475-486
    • Shi, C.1    Szczesniak, A.2    Mao, L.3    Jollimore, C.4    Coca-Prados, M.5    Hung, O.6    Kelly, M.7
  • 48
    • 0037132548 scopus 로고    scopus 로고
    • 3 adenosine receptor gene promoter in transgenic mice: Characterization of previously unidentified sites of expression
    • 3 adenosine receptor gene promoter in transgenic mice: characterization of previously unidentified sites of expression. FEBS Lett. 2002, 532, 267-272.
    • (2002) FEBS Lett. , vol.532 , pp. 267-272
    • Yaar, R.1    Lamperti, E.D.2    Toselli, P.A.3    Ravid, K.4
  • 49
  • 55
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 56
    • 0025143320 scopus 로고
    • A modification of a protein-binding method for rapid quantification of cAMP in cell-culture supernatants and body fluid
    • Nordstedt, C.; Fredholm, B. B. A modification of a protein-binding method for rapid quantification of cAMP in cell-culture supernatants and body fluid. Anal. Biochem. 1990, 189, 231-234.
    • (1990) Anal. Biochem. , vol.189 , pp. 231-234
    • Nordstedt, C.1    Fredholm, B.B.2
  • 57
    • 0033632117 scopus 로고    scopus 로고
    • Biochemical methods for detection and measurement of cyclic AMP and adenylyl cyclase activity
    • Post, S. R.; Ostrom, R. S.; Insel, P. A. Biochemical methods for detection and measurement of cyclic AMP and adenylyl cyclase activity. Methods Mol. Biol. 2000, 126, 363-374.
    • (2000) Methods Mol. Biol. , vol.126 , pp. 363-374
    • Post, S.R.1    Ostrom, R.S.2    Insel, P.A.3
  • 59
  • 60
    • 0001242234 scopus 로고    scopus 로고
    • MMFF VII. Characterization of MMFF94, MMFF94s, and other widely available force fields for conformational energies and for intermolecular-interaction energies and geometries
    • Halgren, T. A. MMFF VII. Characterization of MMFF94, MMFF94s, and other widely available force fields for conformational energies and for intermolecular-interaction energies and geometries. J. Comput. Chem. 1999, 20, 730-748.
    • (1999) J. Comput. Chem. , vol.20 , pp. 730-748
    • Halgren, T.A.1
  • 62
    • 15444363072 scopus 로고    scopus 로고
    • note
    • Residues that were within 5 Å of the ligand in this putative binding site were the following: L91 (3.33), T94 (3.36), H95 (3.37), N150 (EL2), Q167 (EL2), F168 (EL2), S181 (5.42), M177 (5.38), V178 (5.39), F182 (5.43), W243 (6.48), L246 (6.51), S247 (6.52), N250 (6.55), 1268 (7.39), S271 (7.42), and H272 (7.43).
  • 63
    • 15444363469 scopus 로고    scopus 로고
    • note
    • 6-benzyl binding region resulted in weak H-bonding interactions at the hydroxyl and 5′-uronamide groups of methanocarba ring, thus decreasing the binding affinity.
  • 64
    • 15444372779 scopus 로고    scopus 로고
    • note
    • 6-benzyl ring, and its hydroxyl group entered a hydrophilic region.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.