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Volumn 48, Issue 22, 2005, Pages 6887-6896

2-n-butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacological characterization

Author keywords

[No Author keywords available]

Indexed keywords

2 N BUTYL 9 METHYL 8 [1,2,3]TRIAZOL 2 YL 9H PURIN 6 YLAMINE; 4 [2 [7 AMINO 2 (2 FURYL) 1,2,4 TRIAZOLO[2,3 A][1,3,5]TRIAZIN 5 YLAMINO]ETHYL]PHENOL; 5 AMINO 2 (2 FURYL) 7 (2 PHENYLETHYL)PYRAZOLO[4,3 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDINE; 8 CYCLOPENTYL 1,3 DIPROPYLXANTHINE; 9 CHLORO 2 (2 FURYL) 5,6 DIHYDRO 5 IMINO 1,2,4 TRIAZOLO[2,3 C]QUINAZOLINE; 9 METHYL 2 PHENETYL 8 [1,2,3]TRIAZOL 2 YL 9H PURIN 6 YLAMINE; ADENOSINE A1 RECEPTOR; ADENOSINE A2A RECEPTOR; ADENOSINE A2A RECEPTOR ANTAGONIST; ADENOSINE A2B RECEPTOR; ADENOSINE A3 RECEPTOR; ADENOSINE RECEPTOR; ISTRADEFYLLINE; UNCLASSIFIED DRUG;

EID: 27444442267     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm058018d     Document Type: Article
Times cited : (91)

References (41)
  • 1
    • 0031833150 scopus 로고    scopus 로고
    • Adenosine receptors: New opportunities for future drugs
    • (a) Poulsen, S. A.; Quinn, R. J. Adenosine Receptors: New Opportunities for Future Drugs. Bioorg. Med. Chem. 1998, 6, 619-641;
    • (1998) Bioorg. Med. Chem. , vol.6 , pp. 619-641
    • Poulsen, S.A.1    Quinn, R.J.2
  • 2
    • 0030250999 scopus 로고    scopus 로고
    • Pharmacology of adenosine A2A receptors
    • (b) Ongini, E.; Fredholm, B. B. Pharmacology of Adenosine A2A Receptors. Trends Pharmacol. Sci. 1996, 17, 364-372;
    • (1996) Trends Pharmacol. Sci. , vol.17 , pp. 364-372
    • Ongini, E.1    Fredholm, B.B.2
  • 3
    • 0026698249 scopus 로고
    • Molecular characterization of a human brain adenosine A2 receptor
    • (c) Furlong, T. J.; Pierce, K. D.; Selbie, L. A.; Shine, J. Molecular Characterization of a Human Brain Adenosine A2 Receptor. Mol. Brain Res. 1992, 15, 62-66;
    • (1992) Mol. Brain Res. , vol.15 , pp. 62-66
    • Furlong, T.J.1    Pierce, K.D.2    Selbie, L.A.3    Shine, J.4
  • 4
    • 0020647370 scopus 로고
    • Evidence for an A1-adenosine receptor in the guinea-pig atrium
    • (d) Collis, M. G. Evidence for an A1-Adenosine Receptor in the Guinea-Pig Atrium. Br. J. Pharmacol. 1983, 78, 207-212.
    • (1983) Br. J. Pharmacol. , vol.78 , pp. 207-212
    • Collis, M.G.1
  • 6
    • 0037418014 scopus 로고    scopus 로고
    • Adenosine receptor blockade reverses hypophagia and enhances locomotor activity of dopamine-deficient mice
    • Kim, D. S.; Palmiter, R. D. Adenosine Receptor Blockade Reverses Hypophagia and Enhances Locomotor Activity of Dopamine-Deficient Mice. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 1346-1351.
    • (2003) Proc. Natl. Acad. Sci. U.S.A. , vol.100 , pp. 1346-1351
    • Kim, D.S.1    Palmiter, R.D.2
  • 8
    • 2842546966 scopus 로고    scopus 로고
    • Adenosine receptor antagonists: Structures and potential therapeutic applications
    • (b) Mueller, C. E.; Stein, B. Adenosine Receptor Antagonists: Structures and Potential Therapeutic Applications. Curr. Pharm. Des. 1996, 2, 501-530.
    • (1996) Curr. Pharm. Des. , vol.2 , pp. 501-530
    • Mueller, C.E.1    Stein, B.2
  • 10
    • 0033219932 scopus 로고    scopus 로고
    • Actions of adenosine A2A receptor antagonist KW 6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP
    • (b) Shiozaki, S.; Ichikawa, S.; Nakamura, J.; Kitamura, S.; Yamada, K.; Kuwana, Y. Actions of Adenosine A2A Receptor Antagonist KW 6002 on Drug-Induced Catalepsy and Hypokinesia Caused by Reserpine or MPTP. Phychopharmacology 1999, 147, 90-95.
    • (1999) Phychopharmacology , vol.147 , pp. 90-95
    • Shiozaki, S.1    Ichikawa, S.2    Nakamura, J.3    Kitamura, S.4    Yamada, K.5    Kuwana, Y.6
  • 11
    • 0027942203 scopus 로고
    • Synthesis of new pyrazolo-[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine and 1,2,3-triazolo[4,5-e]1,2,4-triazolo[1,5-c]pyrimidine displaying potent and selective activity as A2A adenosine receptor antagonists
    • (a) Baraldi, P. G.; Manfredini, S.; Simoni, D.; Zappaterra, L.; Zocchi, C.; Dionisotti, S.; Ongini, E. Synthesis of New Pyrazolo-[4,3-e]1,2,4- triazolo[1,5-c]pyrimidine and 1,2,3-triazolo[4,5-e]1,2,4-triazolo[1,5-c] pyrimidine Displaying Potent and Selective Activity as A2A Adenosine Receptor Antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 2539-2544;
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2539-2544
    • Baraldi, P.G.1    Manfredini, S.2    Simoni, D.3    Zappaterra, L.4    Zocchi, C.5    Dionisotti, S.6    Ongini, E.7
  • 12
    • 0030075741 scopus 로고    scopus 로고
    • The non-xanthine heterocyclic compound SCH 58261 is a new potent and selective A2A adenosine receptor antagonist
    • (b) Zocchi, C.; Ongini, E.; Conti, A.; Monopoli, A.; Negretti, A.; Baraldi, P. G.; Dionisotti, S. The Non-Xanthine Heterocyclic Compound SCH 58261 is a New Potent and Selective A2A Adenosine Receptor Antagonist. J. Pharmacol. Exp. Ther. 1996, 276, 398-404;
    • (1996) J. Pharmacol. Exp. Ther. , vol.276 , pp. 398-404
    • Zocchi, C.1    Ongini, E.2    Conti, A.3    Monopoli, A.4    Negretti, A.5    Baraldi, P.G.6    Dionisotti, S.7
  • 13
    • 0031432929 scopus 로고    scopus 로고
    • SCH 58261: A selective A2A adenosine receptor antagonist
    • (c) Ongini, E. SCH 58261: a Selective A2A Adenosine Receptor Antagonist. Drug. Dev. Res. 1997, 42, 63-70;
    • (1997) Drug. Dev. Res. , vol.42 , pp. 63-70
    • Ongini, E.1
  • 14
    • 0345269287 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as new A2A and A3 adenosine receptors antagonists
    • (d) Baraldi, P. G.; Fruttarolo, F.; Tabrizi, M. A.; Preti, D.; Romagnoli, R.; El-Kashef, H.; Moorman, A.; Varani, K.; Gessi, S.; Merighi, S.; Borea, P. A. Design, Synthesis, and Biological Evaluation of C9- and C2-Substituted Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as New A2A and A3 Adenosine Receptors Antagonists. J. Med. Chem. 2003, 46, 1229-1241.
    • (2003) J. Med. Chem. , vol.46 , pp. 1229-1241
    • Baraldi, P.G.1    Fruttarolo, F.2    Tabrizi, M.A.3    Preti, D.4    Romagnoli, R.5    El-Kashef, H.6    Moorman, A.7    Varani, K.8    Gessi, S.9    Merighi, S.10    Borea, P.A.11
  • 15
    • 37049081723 scopus 로고
    • Adenine isosteres with bridgehead nitrogen. Part 1. Two independent synthesis of the [1,2,4]triazolo[1,5-a][1,3,5]triazine ring system leading to a range of substituents in the 2, 5 and 7 positions
    • (a) Caulkett, P. W. R.; Jones, G.; McPartlin, M.; Renshaw, N. D.; Stewart, S. K.; Wright, B. Adenine Isosteres with Bridgehead Nitrogen. Part 1. Two Independent Synthesis of the [1,2,4]triazolo[1,5-a][1,3,5]triazine Ring System Leading to a Range of Substituents in the 2, 5 and 7 Positions. J. Chem. Soc., Perkin Trans. 1 1995, 7, 801-808;
    • (1995) J. Chem. Soc., Perkin Trans. 1 , vol.7 , pp. 801-808
    • Caulkett, P.W.R.1    Jones, G.2    McPartlin, M.3    Renshaw, N.D.4    Stewart, S.K.5    Wright, B.6
  • 16
    • 0029127542 scopus 로고
    • The in vitro pharmacology of ZM 241385, a potent, non-xanthine, A2A selective adenosine receptor antagonist
    • (b) Poucher, S. M.; Keddie, J. R.; Singh, P.; Stoggall, S. M.; Caulkett, P. W. R.; Jones, G.; Collis, M. G. The in vitro pharmacology of ZM 241385, a Potent, Non-Xanthine, A2A Selective Adenosine Receptor Antagonist. Br. J. Pharmacol. 1995, 115, 1096-1102.
    • (1995) Br. J. Pharmacol. , vol.115 , pp. 1096-1102
    • Poucher, S.M.1    Keddie, J.R.2    Singh, P.3    Stoggall, S.M.4    Caulkett, P.W.R.5    Jones, G.6    Collis, M.G.7
  • 19
    • 27444434262 scopus 로고    scopus 로고
    • A2A Adenosine Receptor Antagonists. PCT Patent WO03051882, 2003
    • (b) Cristalli, G. A2A Adenosine Receptor Antagonists. PCT Patent WO03051882, 2003.
    • Cristalli, G.1
  • 20
    • 0022523344 scopus 로고
    • 1,3-Dipropyl-8-cyclopentylxanthine (DPCPX) inhibition of [3H]N-ethylcarboxamidoadenosine (NECA) binding allows the visualization of putative non-A1 adenosine receptors
    • (a) Lee, K. S.; Reddington, M. 1,3-Dipropyl-8-cyclopentylxanthine (DPCPX) Inhibition of [3H]N-Ethylcarboxamidoadenosine (NECA) Binding Allows the Visualization of Putative non-A1 Adenosine Receptors. Brain Res. 1986, 368, 394-398;
    • (1986) Brain Res. , vol.368 , pp. 394-398
    • Lee, K.S.1    Reddington, M.2
  • 23
    • 0025925105 scopus 로고
    • N6,9-disubstituted adenines: Potent, selective antagonists at the A1 adenosine receptor
    • Thompson, R. D.; Secunda, S.; Daly, J. W.; Olsson, R. A. N6,9-Disubstituted Adenines: Potent, Selective Antagonists at the A1 Adenosine Receptor. J. Med. Chem. 1991, 34, 2877-2882.
    • (1991) J. Med. Chem. , vol.34 , pp. 2877-2882
    • Thompson, R.D.1    Secunda, S.2    Daly, J.W.3    Olsson, R.A.4
  • 24
    • 0029154004 scopus 로고
    • Synthesis and structure-activity relationships of analogues of 2′-deoxy-2′-(3-methoxybenzamido)adenosine, a selective inhibitor of trypanosomal glycosomal glyceraldehyde-3-phosphate dehydrogenase
    • Calenbergh, S. V.; Verlinde, C. L. M. J.; Soenens, J.; De Bruyn, A.; Callens, M.; Blaton, N. M.; Peeters, O. M.; Rozenski, J.; Hol, W. G. J.; Herdewijn, P. Synthesis and Structure-Activity Relationships of Analogues of 2′-Deoxy-2′-(3-methoxybenzamido)adenosine, a Selective Inhibitor of Trypanosomal Glycosomal Glyceraldehyde-3-phosphate Dehydrogenase. J. Med. Chem. 1995, 38, 3838-3849.
    • (1995) J. Med. Chem. , vol.38 , pp. 3838-3849
    • Calenbergh, S.V.1    Verlinde, C.L.M.J.2    Soenens, J.3    De Bruyn, A.4    Callens, M.5    Blaton, N.M.6    Peeters, O.M.7    Rozenski, J.8    Hol, W.G.J.9    Herdewijn, P.10
  • 26
    • 0028095613 scopus 로고
    • Total synthesis of bleomycin A2 and related agents. 2. Synthesis of (-)-pyrimidoblamic acid, epi-(+)-pyrimidoblamic acid, (+)- desacetamidopyrimidoblamic acid, and (-)-descarboxamidopyrimidoblamic acid
    • Boger, D. L.; Honda, T.; Dang, Q. Total Synthesis of Bleomycin A2 and Related Agents. 2. Synthesis of (-)-Pyrimidoblamic Acid, epi-(+)-Pyrimidoblamic Acid, (+)-Desacetamidopyrimidoblamic Acid, and (-)-Descarboxamidopyrimidoblamic Acid. J. Am. Chem. Soc. 1994, 116, 5619-5630.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5619-5630
    • Boger, D.L.1    Honda, T.2    Dang, Q.3
  • 27
    • 0026758250 scopus 로고
    • Convenient method for the synthesis of C-alkylated purine nucleosides: Palladium-catalyzed cross-coupling reaction of halogenopurine nucleosides with trialkylaluminums
    • Hirota, K.; Kitade, Y.; Kanbe Y.; Maki, Y. Convenient Method for the Synthesis of C-Alkylated Purine Nucleosides: Palladium-Catalyzed Cross-Coupling Reaction of Halogenopurine Nucleosides with Trialkylaluminums. J. Org. Chem. 1992, 57, 5268-5270.
    • (1992) J. Org. Chem. , vol.57 , pp. 5268-5270
    • Hirota, K.1    Kitade, Y.2    Kanbe, Y.3    Maki, Y.4
  • 28
    • 0027431083 scopus 로고
    • Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents
    • (a) Van Aerschot, A. A.; Mamos, P.; Weyns, N. J.; Ikeda, S.; De Clercq, E., Herdewijn, P. A. Antiviral Activity of C-Alkylated Purine Nucleosides Obtained by Cross-Coupling with Tetraalkyltin Reagents. J. Med. Chem. 1993, 36, 2938-2942;
    • (1993) J. Med. Chem. , vol.36 , pp. 2938-2942
    • Van Aerschot, A.A.1    Mamos, P.2    Weyns, N.J.3    Ikeda, S.4    De Clercq, E.5    Herdewijn, P.A.6
  • 29
    • 0020826828 scopus 로고
    • Mechanisms of the palladium-catalyzed couplings of acid chlorides with organotin reagents
    • (b) Labadie, J. W.; Stille, J. K. Mechanisms of the Palladium-Catalyzed Couplings of Acid Chlorides with Organotin Reagents. J. Am. Chem. Soc. 1983, 105, 6129-6137.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6129-6137
    • Labadie, J.W.1    Stille, J.K.2
  • 30
    • 0028013346 scopus 로고
    • Adenosine deaminase inhibitors: Synthesis and structure-activity relationships of 2-hydroxy-3-nonyl derivatives of azoles
    • Cristalli, G.; Eleuteri, A.; Volpini, R.; Vittori, S.; Camaioni E.; Lupidi, G.; Adenosine Deaminase Inhibitors: Synthesis and Structure-Activity Relationships of 2-Hydroxy-3-nonyl Derivatives of Azoles. J. Med. Chem. 1994, 37, 201-205.
    • (1994) J. Med. Chem. , vol.37 , pp. 201-205
    • Cristalli, G.1    Eleuteri, A.2    Volpini, R.3    Vittori, S.4    Camaioni, E.5    Lupidi, G.6
  • 31
    • 27444436330 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of 2-triazolyl derivatives 23b exhibited one singlet at 7.94 ppm characteristic of symmetric compounds, whereas 1-triazolyl derivatives 24b gave two doublets (J = 0.8 Hz) at 7.81 and 8.24 ppm.
  • 32
    • 0024416540 scopus 로고
    • Pyrido[3,4-e]-1,2,4-triazines and related heterocycles as potential antifungal agents
    • (a) Reich, M. F.; Fabio, P. F.; Lee, V. J.; Kuck, N. A.; Testa, R. T. Pyrido[3,4-e]-1,2,4-triazines and Related Heterocycles as Potential Antifungal Agents. J. Med. Chem. 1989, 32, 2474-2485;
    • (1989) J. Med. Chem. , vol.32 , pp. 2474-2485
    • Reich, M.F.1    Fabio, P.F.2    Lee, V.J.3    Kuck, N.A.4    Testa, R.T.5
  • 33
    • 0025339273 scopus 로고
    • A novel preparation of thiazolo[5,4-c]pyridines and the synthesis of some imidazo[4,5-c]pyridines and oxazolo[4,5-c]pyridines
    • (b) Katner, A. S.; Brown, R. F. A Novel Preparation of Thiazolo[5,4-c]pyridines and the Synthesis of Some Imidazo[4,5-c]pyridines and Oxazolo[4,5-c]pyridines. J. Heterocycl. Chem. 1990, 27, 563-566.
    • (1990) J. Heterocycl. Chem. , vol.27 , pp. 563-566
    • Katner, A.S.1    Brown, R.F.2
  • 34
    • 0021910743 scopus 로고
    • Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 8. Molecular dissections of carbocyclic 3-deazaadenosine as inhibitors of S-adenosylhomocysteine hydrolase
    • Houston, D. M.; Dolence, E. K.; Keller, B. T.; Patel-Thombre, U.; Borchardt, R. T. Potential Inhibitors of S-Adenosylmethionine-Dependent Methyltransferases. 8. Molecular Dissections of Carbocyclic 3-Deazaadenosine as Inhibitors of S-Adenosylhomocysteine Hydrolase. J. Med. Chem. 1985, 28, 467-471.
    • (1985) J. Med. Chem. , vol.28 , pp. 467-471
    • Houston, D.M.1    Dolence, E.K.2    Keller, B.T.3    Patel-Thombre, U.4    Borchardt, R.T.5
  • 37
    • 0024471542 scopus 로고
    • Evidence for adenosine A2 receptor involvement in the hypomobility effects of adenosine analogs in mice
    • (a) Durcan, M. J.; Morgan, P. F. Evidence for Adenosine A2 Receptor Involvement in the Hypomobility Effects of Adenosine Analogs in Mice. Eur. J. Pharmacol. 1989, 168, 285-290;
    • (1989) Eur. J. Pharmacol. , vol.168 , pp. 285-290
    • Durcan, M.J.1    Morgan, P.F.2
  • 38
    • 0032584389 scopus 로고    scopus 로고
    • Adenosine A1 and A2A receptor antagonists stimulate motor activity: Evidence for an increased effectiveness in aged rats
    • (b) Popoli, P.; Reggio, R.; Pezzola, A.; Fuxe, K.; Ferre, S. Adenosine A1 and A2A Receptor Antagonists Stimulate Motor Activity: Evidence for an Increased Effectiveness in Aged Rats. Neurosci. Lett. 1998, 251, 201-204;
    • (1998) Neurosci. Lett. , vol.251 , pp. 201-204
    • Popoli, P.1    Reggio, R.2    Pezzola, A.3    Fuxe, K.4    Ferre, S.5
  • 39
    • 0034726038 scopus 로고    scopus 로고
    • SCH 58261 and ZM 241385 differentially prevent the motor effects of CGS 21680 in Mice: Evidence for a functional 'atypical' adenosine A2A receptor
    • (c) El Yacoubi, M.; Ledent, C.; Parmentier, M.; Costentin, J.; Vaugeois, J.-M. SCH 58261 and ZM 241385 Differentially Prevent the Motor Effects of CGS 21680 in Mice: Evidence for a Functional 'Atypical' Adenosine A2A Receptor. Eur. J. Pharmacol. 2000, 401, 63-77.
    • (2000) Eur. J. Pharmacol. , vol.401 , pp. 63-77
    • El Yacoubi, M.1    Ledent, C.2    Parmentier, M.3    Costentin, J.4    Vaugeois, J.-M.5


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