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Volumn 48, Issue 3, 2005, Pages 710-722

Synthesis and biological testing of purine derivatives as potential ATP-competitive kinase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; PROTEIN KINASE INHIBITOR; PURINE DERIVATIVE;

EID: 13444272999     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0408767     Document Type: Article
Times cited : (102)

References (48)
  • 2
    • 0042121318 scopus 로고    scopus 로고
    • Medicinal chemistry of target family-directed masterkeys
    • Mueller, G. Medicinal chemistry of target family-directed masterkeys. Drug Discov. Today 2003, 8, 681-691.
    • (2003) Drug Discov. Today , vol.8 , pp. 681-691
    • Mueller, G.1
  • 5
    • 0033567706 scopus 로고    scopus 로고
    • The structure of phosphorylated p38gamma is monomeric and reveals a conserved activation-loop conformation
    • Bellon, S.; Fitzgibbon, M. J.; Fox, T.; Hsiao, H. M.; Wilson, K. P. The structure of phosphorylated p38gamma is monomeric and reveals a conserved activation-loop conformation. Structure Fold. Des 1999, 7, 1057-1065.
    • (1999) Structure Fold. Des. , vol.7 , pp. 1057-1065
    • Bellon, S.1    Fitzgibbon, M.J.2    Fox, T.3    Hsiao, H.M.4    Wilson, K.P.5
  • 6
    • 0037013143 scopus 로고    scopus 로고
    • The conformational plasticity of protein kinases
    • Huse, M.; Kuriyan, J. The conformational plasticity of protein kinases. Cell (Cambridge, MA) 2002, 109, 275-282.
    • (2002) Cell (Cambridge, MA) , vol.109 , pp. 275-282
    • Huse, M.1    Kuriyan, J.2
  • 7
    • 0031731295 scopus 로고    scopus 로고
    • Tyrosine kinase inhibitors in cancer treatment (part II)
    • Traxler, P. Tyrosine kinase inhibitors in cancer treatment (part II). Exp. Opin. Ther. Patents 1998, 8, 1599-1625.
    • (1998) Exp. Opin. Ther. Patents , vol.8 , pp. 1599-1625
    • Traxler, P.1
  • 8
    • 0030992914 scopus 로고    scopus 로고
    • Protein tyrosine kinase inhibitors in cancer treatment
    • Traxler, P. M. Protein tyrosine kinase inhibitors in cancer treatment. Exp. Opin. Ther. Patents 1997, 7, 571-588.
    • (1997) Exp. Opin. Ther. Patents , vol.7 , pp. 571-588
    • Traxler, P.M.1
  • 9
    • 0035413606 scopus 로고    scopus 로고
    • Kinetic and catalytic mechanisms of protein kinases
    • Adams, J. A. Kinetic and catalytic mechanisms of protein kinases. Chem. Rev. 2001, 101, 2271-2290.
    • (2001) Chem. Rev. , vol.101 , pp. 2271-2290
    • Adams, J.A.1
  • 11
    • 0037665145 scopus 로고    scopus 로고
    • Roscovitine and Other Purines as Kinase Inhibitors. From Starfish Oocytes to Clinical Trials
    • Meijer, L.; Raymond, E. Roscovitine and Other Purines as Kinase Inhibitors. From Starfish Oocytes to Clinical Trials. Acc. Chem. Res. 2003, 36, 417-425.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 417-425
    • Meijer, L.1    Raymond, E.2
  • 14
    • 0029090514 scopus 로고
    • Multiple modes of ligand recognition: Crystal structures of cyclin-dependent protein kinase 2 in complex with ATP and two inhibitors, olomoucine and isopentenyladenine
    • Schulze-Gahmen, U.; Brandsen, J.; Jones, H. D.; Morgan, D. O.; Meijer, L. Multiple modes of ligand recognition: Crystal structures of cyclin-dependent protein kinase 2 in complex with ATP and two inhibitors, olomoucine and isopentenyladenine. Proteins: Struct., Funct., Genet. 1995, 22, 378-391.
    • (1995) Proteins: Struct., Funct., Genet. , vol.22 , pp. 378-391
    • Schulze-Gahmen, U.1    Brandsen, J.2    Jones, H.D.3    Morgan, D.O.4    Meijer, L.5
  • 15
    • 0036716567 scopus 로고    scopus 로고
    • Recent advances in cyclin-dependent kinase inhibition. Purine-based derivatives as anti-cancer agents. Roles and perspectives for the future
    • Haesslein, J. L.; Jullian, N. Recent advances in cyclin-dependent kinase inhibition. Purine-based derivatives as anti-cancer agents. Roles and perspectives for the future. Curr. Top. Med. Chem. 2002, 2, 1037-1050.
    • (2002) Curr. Top. Med. Chem. , vol.2 , pp. 1037-1050
    • Haesslein, J.L.1    Jullian, N.2
  • 16
    • 0036836964 scopus 로고    scopus 로고
    • Development of a Purine-Scaffold Novel Class of Hsp90 Binders that Inhibit the Proliferation of Cancer Cells and Induce the Degradation of Her2 Tyrosine Kinase
    • Chiosis, G.; Lucas, B.; Shtil, A.; Huezo, H.; Rosen, N. Development of a Purine-Scaffold Novel Class of Hsp90 Binders that Inhibit the Proliferation of Cancer Cells and Induce the Degradation of Her2 Tyrosine Kinase. Bioorg. Med. Chem. 2002, 10, 3555-3564.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 3555-3564
    • Chiosis, G.1    Lucas, B.2    Shtil, A.3    Huezo, H.4    Rosen, N.5
  • 18
    • 0036668401 scopus 로고    scopus 로고
    • Protein kinase drugs-optimism doesn't wait on facts
    • Groom, C. R.; Hopkins, A. L. Protein kinase drugs-optimism doesn't wait on facts. Drug. Discov. Today 2002, 7, 801-802.
    • (2002) Drug Discov. Today , vol.7 , pp. 801-802
    • Groom, C.R.1    Hopkins, A.L.2
  • 21
    • 0042915882 scopus 로고    scopus 로고
    • The Structure of JNK3 in Complex with Small Molecule Inhibitors: Structural Basis for Potency and Selectivity
    • Scapin, G.; Patel, S. B.; Lisnock, J.; Becker, J. W.; LoGrasso, P. V. The Structure of JNK3 in Complex with Small Molecule Inhibitors: Structural Basis for Potency and Selectivity. Chem. Biol. 2003, 10, 705-712.
    • (2003) Chem. Biol. , vol.10 , pp. 705-712
    • Scapin, G.1    Patel, S.B.2    Lisnock, J.3    Becker, J.W.4    LoGrasso, P.V.5
  • 22
    • 13444292562 scopus 로고    scopus 로고
    • www.upstate.com/features/kinaseprofiler.
  • 23
    • 13444259992 scopus 로고    scopus 로고
    • (Polaroid Corp.) 6-Chloropurine salts. U.S. Patent 4,405,781, 1981
    • Bader, H.; Chiang, Y. H. (Polaroid Corp.) 6-Chloropurine salts. U.S. Patent 4,405,781, 1981.
    • Bader, H.1    Chiang, Y.H.2
  • 24
    • 0000787522 scopus 로고
    • Potential purine antagonists. IV. Synthesis of some 9-methyl-6- substituted purines
    • Robins, R. K.; Lin, H. H. Potential purine antagonists. IV. Synthesis of some 9-methyl-6-substituted purines. J. Am. Chem. Soc. 1957, 79, 490-494.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 490-494
    • Robins, R.K.1    Lin, H.H.2
  • 26
    • 0027769852 scopus 로고
    • Synthesis of a new series of N-substituted-3-[1-alkyl(aryl)-4-piperidyl] azetidin-2-ones as possible muscarinic agents
    • Cignarella, G.; Villa, S.; Barlocco, D. Synthesis of a new series of N-substituted-3-[1-alkyl(aryl)-4-piperidyl]azetidin-2-ones as possible muscarinic agents. J. Heterocycl. Chem. 1993, 30, 1337-1340.
    • (1993) J. Heterocycl. Chem. , vol.30 , pp. 1337-1340
    • Cignarella, G.1    Villa, S.2    Barlocco, D.3
  • 27
    • 84953887278 scopus 로고
    • Acid amide reactions. XXXIV. 7-Substituted purines and their cleavage into 4,5-diaminopyrimidines
    • Bredereck, H.; Effenberger, F.; Rainer, G. Acid amide reactions. XXXIV. 7-Substituted purines and their cleavage into 4,5-diaminopyrimidines. Justus Liebigs Ann. Chem. 1964, 673, 82-87.
    • (1964) Justus Liebigs Ann. Chem. , vol.673 , pp. 82-87
    • Bredereck, H.1    Effenberger, F.2    Rainer, G.3
  • 28
    • 0028025536 scopus 로고
    • 6-Halopurines in palladium-catalyzed coupling with organotin and organozinc reagents
    • Gundersen, L. L.; Bakkestuen, A. K.; Aasen, J.; Overas, H.; Rise, F. 6-Halopurines in palladium-catalyzed coupling with organotin and organozinc reagents. Tetrahedron 1994, 50, 9743-9756.
    • (1994) Tetrahedron , vol.50 , pp. 9743-9756
    • Gundersen, L.L.1    Bakkestuen, A.K.2    Aasen, J.3    Overas, H.4    Rise, F.5
  • 29
    • 33947474658 scopus 로고
    • Purine nucleosides. I. The synthesis of certain 6-substituted-9- (tetrahydro-2-pyranyl)purines as models of purine deoxynucleosides
    • Robins, R. K.; Godefroi, E. F.; Taylor, E. C.; Lewis, L. R.; Jackson, A. Purine nucleosides. I. The synthesis of certain 6-substituted-9-(tetrahydro-2- pyranyl)purines as models of purine deoxynucleosides. J. Am. Chem. Soc. 1961, 83, 2574-2579.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 2574-2579
    • Robins, R.K.1    Godefroi, E.F.2    Taylor, E.C.3    Lewis, L.R.4    Jackson, A.5
  • 30
    • 0001740904 scopus 로고
    • General method for alkylation and alkenylation of heterocycles
    • Taylor, E. C.; Martin, S. F. General method for alkylation and alkenylation of heterocycles. J. Am. Chem. Soc. 1974, 96, 8095-8101.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 8095-8101
    • Taylor, E.C.1    Martin, S.F.2
  • 31
    • 0034841018 scopus 로고    scopus 로고
    • The Suzuki-Miyaura cross-coupling reactions of 2-, 6- or 8-halopurines with boronic acids leading to 2-, 6- or 8-aryl- and -alkenylpurine derivatives
    • Havelkova, M.; Dvorak, D.; Hocek, M. The Suzuki-Miyaura cross-coupling reactions of 2-, 6- or 8-halopurines with boronic acids leading to 2-, 6- or 8-aryl- and -alkenylpurine derivatives. Synthesis 2001, 1704-1710.
    • (2001) Synthesis , pp. 1704-1710
    • Havelkova, M.1    Dvorak, D.2    Hocek, M.3
  • 33
    • 0031766788 scopus 로고    scopus 로고
    • Synthesis of 8-halopurines by reaction of lithiated purines with appropriate halogen donors
    • Nolsoe, J. M. J.; Gundersen, L. L.; Rise, F. Synthesis of 8-halopurines by reaction of lithiated purines with appropriate halogen donors. Synth. Commun. 1998, 28, 4303-4315.
    • (1998) Synth. Commun. , vol.28 , pp. 4303-4315
    • Nolsoe, J.M.J.1    Gundersen, L.L.2    Rise, F.3
  • 34
    • 13444266565 scopus 로고    scopus 로고
    • (Ortho-McNeil Corporation, Inc.) Preparation of substituted imidazoles useful in the treatment of inflammatory diseases. Patent WO 9847892 A1, 1998
    • Beers, S. A., Malloy, E.; Wachter, M. P.; Wu, W. (Ortho-McNeil Corporation, Inc.) Preparation of substituted imidazoles useful in the treatment of inflammatory diseases. Patent WO 9847892 A1, 1998.
    • Beers, S.A.1    Malloy, E.2    Wachter, M.P.3    Wu, W.4
  • 35
    • 0033178359 scopus 로고    scopus 로고
    • The development therapeutic potential of protein kinase inhibitors
    • Cohen, P. The development therapeutic potential of protein kinase inhibitors. Curr. Opin. Chem. Biol. 1999, 3, 459-465.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 459-465
    • Cohen, P.1
  • 36
    • 0034306450 scopus 로고    scopus 로고
    • Specificity and mechanism of action of some commonly used protein kinase inhibitors
    • Davies, S. P.; Reddy, H.; Caivano, M.; Cohen, P. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem. J. 2000, 351, 95-105.
    • (2000) Biochem. J. , vol.351 , pp. 95-105
    • Davies, S.P.1    Reddy, H.2    Caivano, M.3    Cohen, P.4
  • 37
    • 0023024982 scopus 로고
    • Intracellular compartmentalization of adenosine triphosphate
    • Miller, D. S.; Horowitz, S. B. Intracellular compartmentalization of adenosine triphosphate. J. Biol. Chem. 1986, 261, 13911-13915.
    • (1986) J. Biol. Chem. , vol.261 , pp. 13911-13915
    • Miller, D.S.1    Horowitz, S.B.2
  • 38
    • 0037142301 scopus 로고    scopus 로고
    • From Imidazoles to Pyrimidines: New Inhibitors of Cytokine Release
    • Laufer, S. A.; Wagner, G. K. From Imidazoles to Pyrimidines: New Inhibitors of Cytokine Release. J. Med. Chem. 2002, 45, 2733-2740.
    • (2002) J. Med. Chem. , vol.45 , pp. 2733-2740
    • Laufer, S.A.1    Wagner, G.K.2
  • 39
    • 0343525690 scopus 로고
    • Alternating dependency of cytokinin activity in the number of methylene units in .omega.-phenylalkyl derivatives of some purine cytokinins and 4-substituted pyrido[3,4-d]pyrimidine
    • Nishikawa, S.; Kumazawa, Z.; Kashimura, N.; Nishikimi, Y.; Uemura, S. Alternating dependency of cytokinin activity in the number of methylene units in .omega.-phenylalkyl derivatives of some purine cytokinins and 4-substituted pyrido[3,4-d]pyrimidine. Agric. Biol. Chem. 1986, 50, 2243-2249.
    • (1986) Agric. Biol. Chem. , vol.50 , pp. 2243-2249
    • Nishikawa, S.1    Kumazawa, Z.2    Kashimura, N.3    Nishikimi, Y.4    Uemura, S.5
  • 40
    • 0344168165 scopus 로고
    • Reactivities and electronic aspects of nucleic acid heterocycles. 7. Regiospecific substituent effects in 6-substituted purines as measured by proton magnetic resonance
    • Keck, J. H., Jr.; Simpson, R. A.; Wong, J. L. Reactivities and electronic aspects of nucleic acid heterocycles. 7. Regiospecific substituent effects in 6-substituted purines as measured by proton magnetic resonance. J. Org. Chem. 1978, 43, 2587-2590.
    • (1978) J. Org. Chem. , vol.43 , pp. 2587-2590
    • Keck Jr., J.H.1    Simpson, R.A.2    Wong, J.L.3
  • 41
    • 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
  • 42
    • 33947468247 scopus 로고
    • Synthesis of potential anticancer agents. XVI. S-Substituted derivatives of 6-mercaptopurine
    • Johnston, T. P.; Holum, L. B.; Montgomery, J. A. Synthesis of potential anticancer agents. XVI. S-Substituted derivatives of 6-mercaptopurine. J. Am. Chem. Soc. 1958, 80, 6265-6271.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 6265-6271
    • Johnston, T.P.1    Holum, L.B.2    Montgomery, J.A.3
  • 43
    • 4344660276 scopus 로고
    • Condensed pyrimidine systems. XVI. Purines and thiazolo[5,4-d]pyrimidines from 4-amino-5-formamido-6-mercaptopyrimidines
    • Elion, G. B.; Lange, W. H.; Hitchings, G. H. Condensed pyrimidine systems. XVI. Purines and thiazolo[5,4-d]pyrimidines from 4-amino-5-formamido-6- mercaptopyrimidines. J. Am. Chem. Soc. 1956, 78, 2858-2863.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 2858-2863
    • Elion, G.B.1    Lange, W.H.2    Hitchings, G.H.3
  • 44
    • 0001426503 scopus 로고
    • Synthesis of potential anticancer agents. XXVI. The alkylation of 6-chloropurine
    • Montgomery, J. A.; Temple, C., Jr. Synthesis of potential anticancer agents. XXVI. The alkylation of 6-chloropurine. J. Am. Chem. Soc. 1961, 83, 630-635.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 630-635
    • Montgomery, J.A.1    Temple Jr., C.2
  • 45
    • 0023901350 scopus 로고
    • 6-(Alkylamino)-9-benzyl-9H-purines. A new class of anticonvulsant agents
    • Kelley, J. L.; Krochmal, M. P.; Linn, J. A.; McLean, E. W.; Soroko, F. E. 6-(Alkylamino)-9-benzyl-9H-purines. A new class of anticonvulsant agents. J. Med. Chem. 1988, 31, 606-612.
    • (1988) J. Med. Chem. , vol.31 , pp. 606-612
    • Kelley, J.L.1    Krochmal, M.P.2    Linn, J.A.3    McLean, E.W.4    Soroko, F.E.5
  • 46
    • 13444280562 scopus 로고    scopus 로고
    • (Squibb and Sons E. R.) 9-Benzyladenine antiinflammatory agents and their use. U.S. Patent 3,930,005, 1973
    • Wojnar, R. J., Brittain, R. J.; Bernstein, J.; Losee, K. A. (Squibb and Sons E. R.) 9-Benzyladenine antiinflammatory agents and their use. U.S. Patent 3,930,005, 1973.
    • Wojnar, R.J.1    Brittain, R.J.2    Bernstein, J.3    Losee, K.A.4
  • 47
    • 0033520273 scopus 로고    scopus 로고
    • Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 16. Model studies for the construction of conjugated polymers
    • Aitken, R. A.; Drysdale, M. J.; Hill, L.; Lumbard, K. W.; MacCallum, J. R.; Seth, S. Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 16. Model studies for the construction of conjugated polymers. Tetrahedron 1999, 55, 11039-11050.
    • (1999) Tetrahedron , vol.55 , pp. 11039-11050
    • Aitken, R.A.1    Drysdale, M.J.2    Hill, L.3    Lumbard, K.W.4    MacCallum, J.R.5    Seth, S.6


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