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Volumn 51, Issue 13, 2008, Pages 3777-3787

7-Aminopyrazolo[1,5-a]pyrimidines as potent multitargeted receptor tyrosine kinase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

1 [4 [5 AMINO 3 (1 METHYL 1H PYRAZOL 4 YL)PYRAZOLO[1,5 A]PYRIMIDIN 6 YL]PHENYL] 3 (3 TRIFLUOROMETHYLPHENYL)UREA; ESTRADIOL; PLATELET DERIVED GROWTH FACTOR RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; PYRAZOLO[1,5 A]PYRIMIDINE DERIVATIVE; SERIC GONADOTROPIN; VASCULOTROPIN RECEPTOR;

EID: 46849112796     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701397k     Document Type: Article
Times cited : (51)

References (42)
  • 2
    • 0035902180 scopus 로고    scopus 로고
    • Oncogenic Kinase Signalling
    • Blume-Jensen, P.; Hunter, T. Oncogenic Kinase Signalling. Nature 2001, 411, 355-365.
    • (2001) Nature , vol.411 , pp. 355-365
    • Blume-Jensen, P.1    Hunter, T.2
  • 3
    • 0028951043 scopus 로고
    • Dormancy of micrometastases: Balanced proliferation and apoptosis in the presence of angiogenesis suppression
    • Holmgren, L.; O'Reilly. M. S.; Folkman, J. Dormancy of micrometastases: Balanced proliferation and apoptosis in the presence of angiogenesis suppression. Nat. Med. 1995, 1, 149-153.
    • (1995) Nat. Med , vol.1 , pp. 149-153
    • Holmgren, L.1    O'Reilly, M.S.2    Folkman, J.3
  • 4
    • 0035881307 scopus 로고    scopus 로고
    • Hypoxia and Acidosis Independently Up-Regulate Vascular Endothelial Growth Factor Transcription in Brain Tumors in Vivo
    • Fukumura, D.; Xu, L.; Chen, Y.; Gohongi, T.; Seed, B.; Jain, R. K. Hypoxia and Acidosis Independently Up-Regulate Vascular Endothelial Growth Factor Transcription in Brain Tumors in Vivo. Cancer Res. 2001, 61, 6020-6024.
    • (2001) Cancer Res , vol.61 , pp. 6020-6024
    • Fukumura, D.1    Xu, L.2    Chen, Y.3    Gohongi, T.4    Seed, B.5    Jain, R.K.6
  • 5
    • 0036842215 scopus 로고    scopus 로고
    • Vascular Permeability Factor/Vascular Endothelial Growth Factor: A Critical Cytokine in Tumor Angiogenesis and a Potential Target for Diagnosis and Therapy
    • Dvorak, H. F. Vascular Permeability Factor/Vascular Endothelial Growth Factor: A Critical Cytokine in Tumor Angiogenesis and a Potential Target for Diagnosis and Therapy. J. Clin. Oncol. 2002, 20, 4368-4380.
    • (2002) J. Clin. Oncol , vol.20 , pp. 4368-4380
    • Dvorak, H.F.1
  • 6
    • 27944473690 scopus 로고    scopus 로고
    • VEGF as a Key Mediator of Angiogenesis in Cancer
    • Carmeliet, P. VEGF as a Key Mediator of Angiogenesis in Cancer. Oncology 2005, 69 (Suppl. 3), 4-10.
    • (2005) Oncology , vol.69 , Issue.SUPPL. 3 , pp. 4-10
    • Carmeliet, P.1
  • 7
    • 1842407860 scopus 로고    scopus 로고
    • Vascular development: Cellular and molecular regulation
    • Beck, L.; D'Amore, P. A. Vascular development: cellular and molecular regulation. FASEB J. 1997, 11, 365-373.
    • (1997) FASEB J , vol.11 , pp. 365-373
    • Beck, L.1    D'Amore, P.A.2
  • 8
    • 0026538564 scopus 로고
    • Angiogenesis in the female reproductive system
    • Reynolds, L. P.; Killilea, S. D.; Redmer, D. A. Angiogenesis in the female reproductive system. FASEB J. 1992, 6, 886-892.
    • (1992) FASEB J , vol.6 , pp. 886-892
    • Reynolds, L.P.1    Killilea, S.D.2    Redmer, D.A.3
  • 9
    • 0032101999 scopus 로고    scopus 로고
    • Antiangiogenic tumor therapy: Will it work?
    • Augustin, H. G. Antiangiogenic tumor therapy: will it work? Trends Pharmacol. Sci. 1998, 19, 216-222.
    • (1998) Trends Pharmacol. Sci , vol.19 , pp. 216-222
    • Augustin, H.G.1
  • 10
    • 2442621619 scopus 로고    scopus 로고
    • Discovery and Development of Bevacizumab, an Anti-VEGF Antibody for Treating Cancer
    • Ferrara, N.; Hillan, K. J.; Gerber, H.-P.; Novotny, W. Discovery and Development of Bevacizumab, an Anti-VEGF Antibody for Treating Cancer. Nat. Rev. Drug Discovery 2004, 5, 391-400.
    • (2004) Nat. Rev. Drug Discovery , vol.5 , pp. 391-400
    • Ferrara, N.1    Hillan, K.J.2    Gerber, H.-P.3    Novotny, W.4
  • 11
    • 2342591455 scopus 로고    scopus 로고
    • The Discovery of Receptor Tyrosine Kinases: Targets for Cancer Therapy
    • Gschwind, A.; Fischer, O. M.; Ullrich, A. The Discovery of Receptor Tyrosine Kinases: Targets for Cancer Therapy. Nat. Rev. Cancer 2004, 4, 361-370.
    • (2004) Nat. Rev. Cancer , vol.4 , pp. 361-370
    • Gschwind, A.1    Fischer, O.M.2    Ullrich, A.3
  • 12
    • 20444430119 scopus 로고    scopus 로고
    • Board, R.; Jayson, G. C. Platelet-Derived Growth Factor Receptor (PDGFR): A Target for Anticancer Therapeutics. Drug Resist. Updates 2005, 8, 75-83.
    • Board, R.; Jayson, G. C. Platelet-Derived Growth Factor Receptor (PDGFR): A Target for Anticancer Therapeutics. Drug Resist. Updates 2005, 8, 75-83.
  • 13
    • 0032474915 scopus 로고    scopus 로고
    • Synthesis and Biological Evaluations of 3-Substituted Molindones: A Novel Class of Tyrosine Kinase Inhibitors That Exhibit Selectivity toward Particular Receptor Tyrosine Kinases
    • Sun, L.; Tran, N.; Tang, F.; App, H.; Hirth, P.; McMahon, G.; Tang, C. Synthesis and Biological Evaluations of 3-Substituted Molindones: A Novel Class of Tyrosine Kinase Inhibitors That Exhibit Selectivity toward Particular Receptor Tyrosine Kinases. J. Med. Chem. 1998, 41, 2588-2603.
    • (1998) J. Med. Chem , vol.41 , pp. 2588-2603
    • Sun, L.1    Tran, N.2    Tang, F.3    App, H.4    Hirth, P.5    McMahon, G.6    Tang, C.7
  • 15
    • 0032893263 scopus 로고    scopus 로고
    • SU5416 Is a Potent and Selective Inhibitor of the Vascular Endothelial Growth Factor Receptor (Flk- 1/KDR) That Inhibits Tyrosine Kinase Catalysis, Tumor Vascularization, and Growth of Multiple Tumor Types
    • Fong, T. A. T.; Shawver, L. K.; Sun, L.; Tang, C.; App, H.; Powell, T. J.; Kim, Y. H.; Schreck, R.; Wang, X.; Risau, W.; Ullrich, A.; Hirth, K. P.; McMahon, G. SU5416 Is a Potent and Selective Inhibitor of the Vascular Endothelial Growth Factor Receptor (Flk- 1/KDR) That Inhibits Tyrosine Kinase Catalysis, Tumor Vascularization, and Growth of Multiple Tumor Types. Cancer Res. 1999, 59, 99-106.
    • (1999) Cancer Res , vol.59 , pp. 99-106
    • Fong, T.A.T.1    Shawver, L.K.2    Sun, L.3    Tang, C.4    App, H.5    Powell, T.J.6    Kim, Y.H.7    Schreck, R.8    Wang, X.9    Risau, W.10    Ullrich, A.11    Hirth, K.P.12    McMahon, G.13
  • 16
    • 0034644272 scopus 로고    scopus 로고
    • Sun, L.; Tran, N.; Liang, C.; Hubbard, S.; Tang, F.; Lipson, K.; Schreck, R.; Zhou, Y.; McMahon, G.; Tang, C. Identification of Substituted 3-[(4,5,6,7-Tetrahydro-1H-indol-2-yl)methylene]-1,3-dihydroindol-2-ones as Growth Factor Receptor inhibitors for VEGF-R2 (Flk-1/KDR), FGF-R1, and PDGF-Rβ Tyrosine Kinases. J. Med. Chem. 2000, 43, 2655-2663.
    • Sun, L.; Tran, N.; Liang, C.; Hubbard, S.; Tang, F.; Lipson, K.; Schreck, R.; Zhou, Y.; McMahon, G.; Tang, C. Identification of Substituted 3-[(4,5,6,7-Tetrahydro-1H-indol-2-yl)methylene]-1,3-dihydroindol-2-ones as Growth Factor Receptor inhibitors for VEGF-R2 (Flk-1/KDR), FGF-R1, and PDGF-Rβ Tyrosine Kinases. J. Med. Chem. 2000, 43, 2655-2663.
  • 18
    • 14644440555 scopus 로고    scopus 로고
    • Role of the Vascular Endothelial Growth Factor Pathway in Tumor Growth and Angiogenesis
    • Hicklin, D. J.; Ellis, L. M. Role of the Vascular Endothelial Growth Factor Pathway in Tumor Growth and Angiogenesis. J. Clin. Oncol. 2005, 23, 1011-1027.
    • (2005) J. Clin. Oncol , vol.23 , pp. 1011-1027
    • Hicklin, D.J.1    Ellis, L.M.2
  • 19
    • 26644471951 scopus 로고    scopus 로고
    • Drug Resistance by Evasion of Antiangiogenic Targeting of VEGF Signaling in Late-Stage Pancreatic Islet Tumors
    • Casanovas, O.; Hicklin, D. J.; Bergers, G.; Hanahan, D. Drug Resistance by Evasion of Antiangiogenic Targeting of VEGF Signaling in Late-Stage Pancreatic Islet Tumors. Cancer Cell 2005, 8, 299-309.
    • (2005) Cancer Cell , vol.8 , pp. 299-309
    • Casanovas, O.1    Hicklin, D.J.2    Bergers, G.3    Hanahan, D.4
  • 20
    • 0037468875 scopus 로고    scopus 로고
    • Sun, L.; Liang, C.; Shirazian, S.; Zhou, Y.; Miller, T.; Cui, J.; Fukuda, J. Y.; Chu, J.-Y.; Nematalla, A.; Wang, X.; Chen, H.; Sistla, A.; Luu, T. C.; Tang, F.; Wei, J.; Tang, C. Discovery of 5-[5-Fluoro-2-oxo-1,2-dihydroindol- (3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid (2-Dimethylaminoethyl)amide, a Novel Tyrosine Kinase Inhibitor Targeting Vascular Endothelial and Platelet-Derived Growth Factor Receptor Tyrosine Kinase. J. Med. Chem. 2003, 46, 1116-1119.
    • Sun, L.; Liang, C.; Shirazian, S.; Zhou, Y.; Miller, T.; Cui, J.; Fukuda, J. Y.; Chu, J.-Y.; Nematalla, A.; Wang, X.; Chen, H.; Sistla, A.; Luu, T. C.; Tang, F.; Wei, J.; Tang, C. Discovery of 5-[5-Fluoro-2-oxo-1,2-dihydroindol- (3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid (2-Dimethylaminoethyl)amide, a Novel Tyrosine Kinase Inhibitor Targeting Vascular Endothelial and Platelet-Derived Growth Factor Receptor Tyrosine Kinase. J. Med. Chem. 2003, 46, 1116-1119.
  • 21
    • 4944249117 scopus 로고    scopus 로고
    • Wilhelm, S. M.; Carter, C.; Tang, L.; Wilkie, D.; McNabola, A.; Rong, H.; Chen, C.; Zhang, X.; Vincent, P.; McHugh, M.; Cao, Y.; Shujath, J.; Gawlak, S.; Eveleigh, D.; Rowley, B.; Liu, L.; Adnane, L.; Lynch, M.; Auclair, D.; Taylor, I.; Gedrich, R.; Voznesensky, A.; Riedl, B.; Post, L. E.; Bollag, G.; Trail, P. A. BAY 43-9006 Exhibits Broad Spectrum Oral Antitumor Activity and Targets the RAF/MEK/ERK Pathway and Receptor Tyrosine Kinases Involved in Tumor Progression and Angiogenesis. Cancer Res. 2004, 64, 7099-7109.
    • Wilhelm, S. M.; Carter, C.; Tang, L.; Wilkie, D.; McNabola, A.; Rong, H.; Chen, C.; Zhang, X.; Vincent, P.; McHugh, M.; Cao, Y.; Shujath, J.; Gawlak, S.; Eveleigh, D.; Rowley, B.; Liu, L.; Adnane, L.; Lynch, M.; Auclair, D.; Taylor, I.; Gedrich, R.; Voznesensky, A.; Riedl, B.; Post, L. E.; Bollag, G.; Trail, P. A. BAY 43-9006 Exhibits Broad Spectrum Oral Antitumor Activity and Targets the RAF/MEK/ERK Pathway and Receptor Tyrosine Kinases Involved in Tumor Progression and Angiogenesis. Cancer Res. 2004, 64, 7099-7109.
  • 22
    • 24944543833 scopus 로고    scopus 로고
    • Dai, Y.; Guo, Y.; Frey, R. R.; Ji, Z.; Curtin, M. L.; Ahmed, A. A.; Albert, D. H.; Arnold, L.; Arries, S. S.; Bariozzari, T.; Bauch, J. L.; Bouska, J. J.; Bousquet, P. F.; Cunha, G. A.; Glaser, K. B.; Guo, J.; Li, J.; Marcotte, P. A.; Marsh, K. C.; Moskey, M. D.; Pease, L. J.; Stewart, K. D.; Stoll, V. S.; Tapang, P.; Wishart, N.; Davidsen, S. K.; Michaelides, M. R. Thienopyrimidine Ureas as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors. J. Med. Chem. 2005, 48, 6066-6083.
    • Dai, Y.; Guo, Y.; Frey, R. R.; Ji, Z.; Curtin, M. L.; Ahmed, A. A.; Albert, D. H.; Arnold, L.; Arries, S. S.; Bariozzari, T.; Bauch, J. L.; Bouska, J. J.; Bousquet, P. F.; Cunha, G. A.; Glaser, K. B.; Guo, J.; Li, J.; Marcotte, P. A.; Marsh, K. C.; Moskey, M. D.; Pease, L. J.; Stewart, K. D.; Stoll, V. S.; Tapang, P.; Wishart, N.; Davidsen, S. K.; Michaelides, M. R. Thienopyrimidine Ureas as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors. J. Med. Chem. 2005, 48, 6066-6083.
  • 24
    • 33646586669 scopus 로고    scopus 로고
    • Albert, D. H.; Tapang, P.; Magoc, T. J.; Pease, L. J.; Reuter, D. R.; Wer, R.-Q.; Li, J.; Guo, J.; Bousquet, P. F.; Ghoreishi-Haack, N. S.; Wang, B.; Bukofzer, G. T.; Wang, Y.-C.; Stavropoulos, J. A.; Hartandi, K.; Niquette, A. L.; Soni, N.; Johnson, E. F.; McCall, J. O.; Bouska, J. J.; Luo, Y.; Donawho, C. K.; Dai, Y.; Marcotte, P. A.; Glaser, K. B.; Michaelides, M. R.; Davidsen, S. K. Preclinical activity of ABT-869, a multitargeted receptor tyrosine kinase inhibitor. Mol. Cancer Ther. 2006, 5, 995-1006.
    • (a) Albert, D. H.; Tapang, P.; Magoc, T. J.; Pease, L. J.; Reuter, D. R.; Wer, R.-Q.; Li, J.; Guo, J.; Bousquet, P. F.; Ghoreishi-Haack, N. S.; Wang, B.; Bukofzer, G. T.; Wang, Y.-C.; Stavropoulos, J. A.; Hartandi, K.; Niquette, A. L.; Soni, N.; Johnson, E. F.; McCall, J. O.; Bouska, J. J.; Luo, Y.; Donawho, C. K.; Dai, Y.; Marcotte, P. A.; Glaser, K. B.; Michaelides, M. R.; Davidsen, S. K. Preclinical activity of ABT-869, a multitargeted receptor tyrosine kinase inhibitor. Mol. Cancer Ther. 2006, 5, 995-1006.
  • 25
    • 34147137124 scopus 로고    scopus 로고
    • Dai, Y.; Hartandi, K.; Ji, Z.; Ahmed, A. A.; Albert, D. H.; Bauch, J. L.; Bouska, J. J.; Bousquet, P. F.; Cunha, G. A.; Glaser, K. B.; Harris, C. M.; Hickman, D.; Guo, J.; Li, J.; Marcotte, P. A.; Marsh, K. C.; Moskey, M. D.; Martin, R. L.; Olson, A. M.; Osterling, D. J.; Pease, L. J.; Soni, N. B.; Stewart, K. D.; Stoll, V. S.; Tapang, P.; Reuter, D. R.; Davidsen, S. K.; Michaelides, M. R. Discovery of N-(4-(3-Amino-1H-indazol-4-yl) phenyl)-N′-(2-fluoro-5-methylphenyl)urea (ABT-869), a 3-Aminoindazole-Based Orally Active Multitargeted Receptor Tyrosine Kinase Inhibitor. J. Med. Chem. 2007, 50, 1584-1597.
    • (b) Dai, Y.; Hartandi, K.; Ji, Z.; Ahmed, A. A.; Albert, D. H.; Bauch, J. L.; Bouska, J. J.; Bousquet, P. F.; Cunha, G. A.; Glaser, K. B.; Harris, C. M.; Hickman, D.; Guo, J.; Li, J.; Marcotte, P. A.; Marsh, K. C.; Moskey, M. D.; Martin, R. L.; Olson, A. M.; Osterling, D. J.; Pease, L. J.; Soni, N. B.; Stewart, K. D.; Stoll, V. S.; Tapang, P.; Reuter, D. R.; Davidsen, S. K.; Michaelides, M. R. Discovery of N-(4-(3-Amino-1H-indazol-4-yl) phenyl)-N′-(2-fluoro-5-methylphenyl)urea (ABT-869), a 3-Aminoindazole-Based Orally Active Multitargeted Receptor Tyrosine Kinase Inhibitor. J. Med. Chem. 2007, 50, 1584-1597.
  • 26
    • 27544479318 scopus 로고    scopus 로고
    • The development of RTK inhibitors in the clinic has been extensively reviewed. For recent reviews, see the following: (a) Arora, A.; Scholar, E. M. Role of Tyrosine Kinase Inhibitors in Cancer Therapy. J. Pharmacol. Exp. Ther. 2005, 315, 971-979.
    • The development of RTK inhibitors in the clinic has been extensively reviewed. For recent reviews, see the following: (a) Arora, A.; Scholar, E. M. Role of Tyrosine Kinase Inhibitors in Cancer Therapy. J. Pharmacol. Exp. Ther. 2005, 315, 971-979.
  • 27
    • 0037232108 scopus 로고    scopus 로고
    • Small Molecule Tyrosine Kinase Inhibitors: Clinical Development of Anticancer Agents
    • (b) Laird, A. D.; Cherrington, J. M. Small Molecule Tyrosine Kinase Inhibitors: Clinical Development of Anticancer Agents. Expert Opin. Invest. Drugs 2003, 12, 51-64.
    • (2003) Expert Opin. Invest. Drugs , vol.12 , pp. 51-64
    • Laird, A.D.1    Cherrington, J.M.2
  • 29
    • 0033026444 scopus 로고    scopus 로고
    • Strategies toward the Design of Novel and Selective Protein Tyrosine Kinase Inhibitors
    • Traxler, P.; Furet, P. Strategies toward the Design of Novel and Selective Protein Tyrosine Kinase Inhibitors. Pharmacol. Ther. 1999, 82, 195-206.
    • (1999) Pharmacol. Ther , vol.82 , pp. 195-206
    • Traxler, P.1    Furet, P.2
  • 31
    • 84987262992 scopus 로고
    • Etude de la Réaction du β-Aminocrotonitrile et du α-Formyl Phénylacétonitrile avec l'Hydrazine: Synthèse d'Amino-7-pyrazolo[1,5-a]pyrimidines.
    • Alcade, E.; deMendoza, J.; Garcia-Marquina, J. M.; Almera, C.; Elguero, J. Etude de la Réaction du β-Aminocrotonitrile et du α-Formyl Phénylacétonitrile avec l'Hydrazine: Synthèse d'Amino-7-pyrazolo[1,5-a]pyrimidines. J. Heterocycl. Chem. 1974, 11, 423-429.
    • (1974) J. Heterocycl. Chem , vol.11 , pp. 423-429
    • Alcade, E.1    deMendoza, J.2    Garcia-Marquina, J.M.3    Almera, C.4    Elguero, J.5
  • 32
    • 2042507954 scopus 로고    scopus 로고
    • Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483.
    • Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483.
  • 34
    • 0036873950 scopus 로고    scopus 로고
    • Pyrazolopyrimidines Based on 5-Aminopyrazoles Unsubstituted at the Position 1
    • Nam, N. L.; Grandberg, I. I.; Sorokin, V. I. Pyrazolopyrimidines Based on 5-Aminopyrazoles Unsubstituted at the Position 1. Chem. Heterocycl. Compd. 2002, 38, 1371-1374.
    • (2002) Chem. Heterocycl. Compd , vol.38 , pp. 1371-1374
    • Nam, N.L.1    Grandberg, I.I.2    Sorokin, V.I.3
  • 39
    • 0034751861 scopus 로고    scopus 로고
    • Adult Tissue Angiogenesis: Evidence for Negative Regulation by Estrogen in the Uterus
    • Ma, W.; Tan, J.; Matsumoto, H.; Robert, B.; Abrahamson, D. R.; Das, S. K.; Dey, S. K. Adult Tissue Angiogenesis: Evidence for Negative Regulation by Estrogen in the Uterus. Mol. Endocrinol. 2001, 15, 1983-1992.
    • (2001) Mol. Endocrinol , vol.15 , pp. 1983-1992
    • Ma, W.1    Tan, J.2    Matsumoto, H.3    Robert, B.4    Abrahamson, D.R.5    Das, S.K.6    Dey, S.K.7
  • 40
    • 46849096800 scopus 로고    scopus 로고
    • Inhibition values exceeding 30% were significantly different (p < 0.05) from vehicle-treated controls.
    • Inhibition values exceeding 30% were significantly different (p < 0.05) from vehicle-treated controls.
  • 41
    • 46849117845 scopus 로고    scopus 로고
    • 50 < 1000 nM at lower ATP concentration included Src, Lck, JAK2, Abl, and Fyn. Without inhibition data at 1 mM ATP, however, it is not possible to make a direct comparison of these screening data with the data reported in Table 7.
    • 50 < 1000 nM at lower ATP concentration included Src, Lck, JAK2, Abl, and Fyn. Without inhibition data at 1 mM ATP, however, it is not possible to make a direct comparison of these screening data with the data reported in Table 7.


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