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Volumn 41, Issue 1, 1998, Pages 46-52

Flavonoid derivatives as adenosine receptor antagonists: A comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; ADENOSINE A3 RECEPTOR; ADENOSINE A3 RECEPTOR ANTAGONIST; ALPHA NAPHTHOFLAVONE; APIGENIN; CIRSIMARITIN; FLAVONOID; GALANGIN; HISPIDULIN; PENTAMETHYLMORIN; QUERCETIN; RHAMNETIN; UNCLASSIFIED DRUG; VISNAGIN;

EID: 15444338833     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970446z     Document Type: Article
Times cited : (56)

References (34)
  • 1
    • 0030441568 scopus 로고    scopus 로고
    • Recent Developments in Selective Agonists and Antagonists Acting at Purine and Pyrimidine Receptors
    • Jacobson, K. A.; Suzuki, F. Recent Developments in Selective Agonists and Antagonists Acting at Purine and Pyrimidine Receptors. Drug Dev. Res. 1997, 39, 289-300.
    • (1997) Drug Dev. Res. , vol.39 , pp. 289-300
    • Jacobson, K.A.1    Suzuki, F.2
  • 2
    • 0031007914 scopus 로고    scopus 로고
    • AI Adenosine Receptor Antagonists
    • Müller, C. AI Adenosine Receptor Antagonists. Exp. Opin. Ther. Patents 1997, 7, 419-440.
    • (1997) Exp. Opin. Ther. Patents , vol.7 , pp. 419-440
    • Müller, C.1
  • 4
    • 0029998603 scopus 로고    scopus 로고
    • Direct Preconditioning of Cultured Chick Ventricular Myocytes: Novel Functions of Cardiac Adenosine AZA and as Receptors
    • Strickler, J.; Jacobson, K A.; Liang, B. T. Direct Preconditioning of Cultured Chick Ventricular Myocytes: Novel Functions of Cardiac Adenosine AZA and AS Receptors. J. Clin. Invest. 1996, 74, 1773-1779.
    • (1996) J. Clin. Invest. , vol.74 , pp. 1773-1779
    • Strickler, J.1    Jacobson, K.A.2    Liang, B.T.3
  • 5
    • 0029915543 scopus 로고    scopus 로고
    • Inhibition of TNF-alpha Expression by Adenosine-Role of as Adenosine Receptors
    • Sajjadi, F. G.; Takabayashi, K.; Foster, A. C.; Domingo, R. C.; Firestein, G. S. Inhibition of TNF-alpha Expression by Adenosine-Role of AS Adenosine Receptors. J. Immunol. 1996, 756, 3435-3442.
    • (1996) J. Immunol. , vol.756 , pp. 3435-3442
    • Sajjadi, F.G.1    Takabayashi, K.2    Foster, A.C.3    Domingo, R.C.4    Firestein, G.S.5
  • 6
    • 0030051539 scopus 로고    scopus 로고
    • Interactions of Flavonoids and Other Phytochemicals with Adenosine Receptors
    • Ji, X.-d.; Melman, N.; Jacobson, K. A. Interactions of Flavonoids and Other Phytochemicals with Adenosine Receptors. J. Med. Chem. 1996, 39, 781-788.
    • (1996) J. Med. Chem. , vol.39 , pp. 781-788
    • Ji, X.-D.1    Melman, N.2    Jacobson, K.A.3
  • 7
    • 0029893998 scopus 로고    scopus 로고
    • Synthesis and Biological-Activities of Flavonoid Derivatives as as Adenosine Receptor Antagonists
    • Karton, Y.; Jiang, J. L.; Ji, X.-d.; Melman, N.; Olah, M. E.; Stiles, G. L.; Jacobson, K. A. Synthesis and Biological-Activities of Flavonoid Derivatives as as Adenosine Receptor Antagonists. J. Med. Chem. 1996, 39, 2293-2301.
    • (1996) J. Med. Chem. , vol.39 , pp. 2293-2301
    • Karton, Y.1    Jiang, J.L.2    Ji, X.-D.3    Melman, N.4    Olah, M.E.5    Stiles, G.L.6    Jacobson, K.A.7
  • 8
    • 0029977331 scopus 로고    scopus 로고
    • Interaction of 1, 4-Dihydropyridine and Pyridine Derivatives with Adenosine Receptors - Selectivity for as Receptors
    • van Rhee, A. M.; Jiang, J. L.; Melman, N.; Olah, M. E.; Stiles, G. L.; Jacobson, K. A. Interaction of 1, 4-Dihydropyridine and Pyridine Derivatives with Adenosine Receptors - Selectivity for As Receptors. J. Med. Chem. 1996, 39, 2980-2989.
    • (1996) J. Med. Chem. , vol.39 , pp. 2980-2989
    • Rhee, A.M.1    Jiang, J.L.2    Melman, N.3    Olah, M.E.4    Stiles, G.L.5    Jacobson, K.A.6
  • 9
    • 0030796012 scopus 로고    scopus 로고
    • Structure Activity Relationships of 4-Phenylethynyl-6-phenyl-l, 4-dihydropyridines as Highly Selective as Adenosine Receptor Antagonists
    • Jiang, J.-l.; van Rhee, A. M.; Chang, L.; Patchornik, A.; Evans, P.; Melman, N.; Jacobson, K. A. Structure Activity Relationships of 4-Phenylethynyl-6-phenyl-l, 4-dihydropyridines as Highly Selective AS Adenosine Receptor Antagonists J. Med. Chem. 1997, 40, 2596-2608.
    • (1997) J. Med. Chem. , vol.40 , pp. 2596-2608
    • Jiang, J.-L.1    Van Rhee, A.M.2    Chang, L.3    Patchornik, A.4    Evans, P.5    Melman, N.6    Jacobson, K.A.7
  • 10
    • 0029842517 scopus 로고    scopus 로고
    • Derivatives of the Triazoloquinazoline Adenosine Antagonist (CGS15943) are Selective for the Human as Receptor Subtype
    • Kirn, Y.-C.; Ji, X.-d.; Jacobson, K. A. Derivatives of the Triazoloquinazoline Adenosine Antagonist (CGS15943) are Selective for the Human As Receptor Subtype. J. Med. Chem. 1996, 39, 4142-4148.
    • (1996) J. Med. Chem. , vol.39 , pp. 4142-4148
    • Kirn, Y.-C.1    Ji, X.-D.2    Jacobson, K.A.3
  • 13
    • 0029146120 scopus 로고
    • As Adenosine Receptors: Design of Selective Ligands and Therapeutic Prospects
    • Jacobson, K. A.; Kim, H. O.; Siddiqi, S. M.; Olah, M. E.; Stiles, G.; von Lubitz, D. K. J. E. As Adenosine Receptors: Design of Selective Ligands and Therapeutic Prospects. Drugs Future 1995, 20, 689-699.
    • (1995) Drugs Future , vol.20 , pp. 689-699
    • Jacobson, K.A.1    Kim, H.O.2    Siddiqi, S.M.3    Olah, M.E.4    Stiles, G.5    Lubitz, K.J.E.6
  • 15
    • 0030497573 scopus 로고    scopus 로고
    • Activation of Phosphoinositide Breakdown in a Rat RBL-2H3 Mast Cell Line by Adenosine Analogues: Lack of Correlation with Affinity for ASAdenosine Receptor
    • Shin, Y.; Daly, J. W.; Jacobson, K. A. Activation of Phosphoinositide Breakdown in a Rat RBL-2H3 Mast Cell Line by Adenosine Analogues: Lack of Correlation with Affinity for ASAdenosine Receptor. Drug Dev. Res. 1996, 39, 36-46.
    • (1996) Drug Dev. Res. , vol.39 , pp. 36-46
    • Shin, Y.1    Daly, J.W.2    Jacobson, K.A.3
  • 18
    • 0024243178 scopus 로고
    • Some Biological Properties of Plant Flavonoids
    • Middleton, E., Jr. Some Biological Properties of Plant Flavonoids. Ann. Allergy 1988, 61 53-57.
    • (1988) Ann. Allergy , vol.61 , pp. 53-57
    • Middleton Jr., E.1
  • 19
    • 0027372876 scopus 로고
    • Effects of Flavonoids on the Release of Reactive Oxygen Species by Stimulated Human Nëutrophils. Multivariate Analysis of Structure-Activity Relationships (SAR)
    • Limasset, B.; le Doucen, C.; Dore, J. C.; Ojasoo, T.; Dämon, M.; Crastes de Faulet, A. Effects of Flavonoids on the Release of Reactive Oxygen Species by Stimulated Human Nëutrophils. Multivariate Analysis of Structure-Activity Relationships (SAR). Biochem. Pharmacol. 1993 46: 1257-1271.
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 1257-1271
    • Limasset, B.1    Le Doucen, C.2    Dore, J.C.3    Ojasoo, T.4    Dämon, M.5    De Crastes Faulet, A.6
  • 20
    • 0028924311 scopus 로고
    • Three-Dimensional Quantitative Structure-activity Relationship (QSAR) of HIV Integrase Inhibitors: A Comparative Molecular Field Analysis (CoMFA) Study
    • Raghavan, K.; Buolamwini, J. K.; Kohn, K. W.; Weinstein, J. N. Three-Dimensional Quantitative Structure-activity Relationship (QSAR) of HIV Integrase Inhibitors: A Comparative Molecular Field Analysis (CoMFA) Study. J. Med. Chem. 1995, 38, 890-897.
    • (1995) J. Med. Chem. , vol.38 , pp. 890-897
    • Raghavan, K.1    Buolamwini, J.K.2    Kohn, K.W.3    Weinstein, J.N.4
  • 22
    • 33847459390 scopus 로고    scopus 로고
    • The program SYBYL 6.3 is available from TRIPOS Associates, St. Louis, MO, 1993.
    • The program SYBYL 6.3 is available from TRIPOS Associates, St. Louis, MO, 1993.
  • 23
    • 33847469840 scopus 로고    scopus 로고
    • MOPAC 6.0 available from Quantum Chemistry Program Excange.
    • MOPAC 6.0 available from Quantum Chemistry Program Excange.
  • 25
    • 0018934577 scopus 로고
    • Characterization of adenosine receptors in rat brain by (-)[3H]N6-phenylisopropyladenosine
    • Schwabe, U.; Trost, T. Characterization of adenosine receptors in rat brain by (-)[3H]N6-phenylisopropyladenosine. NaunynSchmiedeberg's Arch. Pharmacol. 1980, 373, 179-187.
    • (1980) NaunynSchmiedeberg's Arch. Pharmacol. , vol.373 , pp. 179-187
    • Schwabe, U.1    Trost, T.2
  • 26
    • 0024854441 scopus 로고
    • [3H]CGS 21680, an A2 Selective Adenosine Receptor Agonist Directly Labels A2 Receptors in Rat Brain Tissue
    • Jarvis, M. F.; Schutz, R.; Hutchison, A. J.; Do, E.; Sills, M. A.; Williams, M. [3H]CGS 21680, an A2 Selective Adenosine Receptor Agonist Directly Labels A2 Receptors in Rat Brain Tissue. J. Pharmacol. Exp. Ther. 1989, 251, 888-893.
    • (1989) J. Pharmacol. Exp. Ther. , vol.251 , pp. 888-893
    • Jarvis, M.F.1    Schutz, R.2    Hutchison, A.J.3    Do, E.4    Sills, M.A.5    Williams, M.6
  • 27
    • 0028179205 scopus 로고
    • [125I]AB-MECA, a High Affinity Radioligand for the Rat AI Adenosine Receptor
    • Olah, M. E.; Gallo-Rodriguez, C.; Jacobson, K. A.; Stiles, G. L. [125I]AB-MECA, a High Affinity Radioligand for the Rat AI Adenosine Receptor. Mol. Pharmacol. 1994, 45, 978-982.
    • (1994) Mol. Pharmacol. , vol.45 , pp. 978-982
    • Olah, M.E.1    Gallo-Rodriguez, C.2    Jacobson, K.A.3    Stiles, G.L.4
  • 28
    • 84988129057 scopus 로고
    • Optimization of Paramiters for Semiempirical Methods I. Methods
    • Stewart, J. J. P. Optimization of Paramiters for Semiempirical Methods I. Methods. J. Comput. Chem. 1989, 10, 209-217.
    • (1989) J. Comput. Chem. , vol.10 , pp. 209-217
    • Stewart, J.J.P.1
  • 29
    • 24444468650 scopus 로고
    • Ground States of Molecules. 38. the MNDO method. Approximations and Parameters
    • Dewar, M. J. S.; Thiel, W. Ground States of Molecules. 38. The MNDO method. Approximations and Parameters. J. Am. Chem. Soc. 1977, 09, 4899-4905.
    • (1977) J. Am. Chem. Soc. , vol.9 , pp. 4899-4905
    • Dewar, M.J.S.1    Thiel, W.2
  • 30
    • 0842341771 scopus 로고
    • AMI: A New General Purpose Quantum Mechanical Molecular Model
    • Dewar, M. J. S. E.; Zoebisch, G.; Healy, E. F. AMI: A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 707, 3902-3909.
    • (1985) J. Am. Chem. Soc. , vol.707 , pp. 3902-3909
    • Dewar, J.S.E.1    Zoebisch, G.2    Healy, E.F.3
  • 31
    • 84988098098 scopus 로고
    • Atomic Charges Derived from Electrostatic Potentials: A Detailed Study
    • Chirlian, L. E.; Francl, M M. Atomic Charges Derived from Electrostatic Potentials: A Detailed Study. J. Comput. Chem. 1987, 8, 894-905.
    • (1987) J. Comput. Chem. , vol.8 , pp. 894-905
    • Chirlian, L.E.1    Francl, M.M.2
  • 32
    • 0001681052 scopus 로고
    • The Covariance Problem in Linear Regression. the Partial Least Squares (PLS) Approach to Generalized Inverses
    • Wold, S.; Ruhe, A.; Wold, H.; Dunn, W. J. The Covariance Problem in Linear Regression. The Partial Least Squares (PLS) Approach to Generalized Inverses. SIAM J. Sci. Stat. Comput. 1994, 5 (3), 735-743.
    • (1994) SIAM J. Sci. Stat. Comput. , vol.5 , Issue.3 , pp. 735-743
    • Wold, S.1    Ruhe, A.2    Wold, H.3    Dunn, W.J.4
  • 33
    • 84987100711 scopus 로고
    • Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR Studies
    • Cramer, R. D.; Bunce, J. D.; Patterson, D. E.; Frank, I. E. Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR Studies. Quantum Struct.-Act. Eelat. 1988, 7, 18-25.
    • (1988) Quantum Struct.-Act. Eelat. , vol.7 , pp. 18-25
    • Cramer, R.D.1    Bunce, J.D.2    Patterson, D.E.3    Frank, I.E.4
  • 34
    • 0027762073 scopus 로고
    • ThreeDimensional QSAR of Human Immunodeficiency Virus (I) Protease Inhibitors. 1. a CoMFA Study Employing Experimentally-Determined Alignment Rules
    • Waller, C. L.; Oprea, T. I.; Giolitti, A.; Marshall, G. R. ThreeDimensional QSAR of Human Immunodeficiency Virus (I) Protease Inhibitors. 1. A CoMFA Study Employing Experimentally-Determined Alignment Rules. J. Med. Chem. 1993, 36, 4152-4160.
    • (1993) J. Med. Chem. , vol.36 , pp. 4152-4160
    • Waller, C.L.1    Oprea, T.I.2    Giolitti, A.3    Marshall, G.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.