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Volumn 48, Issue 24, 2005, Pages 7560-7581

2-(Quinazolin-4-ylamino)-[1,4]benzoquinones as covalent-binding, irreversible inhibitors of the kinase domain of vascular endothelial growth factor receptor-2

Author keywords

[No Author keywords available]

Indexed keywords

(2,5 DIMETHOXYPHENYL)(6,7 QUINAZOLIN 4 YL)AMINE; 2 (QUINAZOLIN 4 YLAMINO)[1,4]BENZOQUINONE DERIVATIVE; 2 CHLORO 5 (6,7 QUINAZOLIN 4 YLAMINO)[1,4]BENZOQUINONE DERIVATIVE; ALCOHOL; AMINE; AMMONIUM NITRATE; ANILINE DERIVATIVE; BENZOQUINONE DERIVATIVE; CHLORINE; GLUTATHIONE; PHENOL; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 2;

EID: 28144459983     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050559f     Document Type: Article
Times cited : (78)

References (47)
  • 1
    • 0034648765 scopus 로고    scopus 로고
    • Angiogenesis in cancer and other diseases
    • Carmeliet, P.; Jain, R. K. Angiogenesis in cancer and other diseases. Nature 2000, 407, 249-257.
    • (2000) Nature , vol.407 , pp. 249-257
    • Carmeliet, P.1    Jain, R.K.2
  • 3
    • 0036984640 scopus 로고    scopus 로고
    • Role of angiogenesis in tumor growth and metastasis
    • Folkman, J. Role of angiogenesis in tumor growth and metastasis. Sem. Oncol. 2002, 29, 15-18.
    • (2002) Sem. Oncol. , vol.29 , pp. 15-18
    • Folkman, J.1
  • 4
    • 2942590261 scopus 로고    scopus 로고
    • Vascular endothelial growth factor as a target for anticancer therapy
    • Ferrara, N. Vascular endothelial growth factor as a target for anticancer therapy. Oncologist 2004, 9 Suppl 1, 2-10.
    • (2004) Oncologist , vol.9 , Issue.SUPPL. 1 , pp. 2-10
    • Ferrara, N.1
  • 5
    • 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
  • 6
    • 0025717523 scopus 로고
    • Inhibition of tumor angiogenesis as a strategy to circumvent acquired resistance to anti-cancer therapeutic agents
    • Kerbel, R. S. Inhibition of tumor angiogenesis as a strategy to circumvent acquired resistance to anti-cancer therapeutic agents. Bioessays 1991, 13, 31-36.
    • (1991) Bioessays , vol.13 , pp. 31-36
    • Kerbel, R.S.1
  • 7
    • 0034032882 scopus 로고    scopus 로고
    • Antiangiogenic scheduling of chemotherapy improves efficacy against experimental drug-resistant cancer
    • Browder, T.; Butterfield, C. E.; Kraling, B. M.; Shi, B.; Marshall, B.; O'Reilly, M. S.; Folkman, J. Antiangiogenic scheduling of chemotherapy improves efficacy against experimental drug-resistant cancer. Can. Res. 2000, 60, 1878-1886.
    • (2000) Can. Res. , vol.60 , pp. 1878-1886
    • Browder, T.1    Butterfield, C.E.2    Kraling, B.M.3    Shi, B.4    Marshall, B.5    O'Reilly, M.S.6    Folkman, J.7
  • 8
    • 2942615257 scopus 로고    scopus 로고
    • The anti-angiogenic basis of metronomic chemotherapy
    • Kerbel, R. S.; Kamen, B. A. The anti-angiogenic basis of metronomic chemotherapy. Nature Rev. Cancer 2004, 4, 423-436.
    • (2004) Nature Rev. Cancer , vol.4 , pp. 423-436
    • Kerbel, R.S.1    Kamen, B.A.2
  • 9
    • 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 Dis. 2004, 3, 391-400.
    • (2004) Nat. Rev. Drug Dis. , vol.3 , pp. 391-400
    • Ferrara, N.1    Hillan, K.J.2    Gerber, H.P.3    Novotny, W.4
  • 10
    • 0036023438 scopus 로고    scopus 로고
    • Anti-vascular endothelial growth factor receptor 2 antibody reduces tumorigenicity and metastasis in orthotopic prostate cancer xenografts via induction of endothelial cell apoptosis and reduction of endothelial cell matrix metalloproteinase type 9 production
    • Sweeney, P.; Karashima, T.; Kim, S. J.; Kedar, D.; Mian, B.; Huang, S., Baker, C.; Fan, Z.; Hicklin, D. J.; Pettaway, C. A.; Dinney, C. P. Anti-vascular endothelial growth factor receptor 2 antibody reduces tumorigenicity and metastasis in orthotopic prostate cancer xenografts via induction of endothelial cell apoptosis and reduction of endothelial cell matrix metalloproteinase type 9 production. Clin. Cancer Res. 2002, 8, 2714-2724.
    • (2002) Clin. Cancer Res. , vol.8 , pp. 2714-2724
    • Sweeney, P.1    Karashima, T.2    Kim, S.J.3    Kedar, D.4    Mian, B.5    Huang, S.6    Baker, C.7    Fan, Z.8    Hicklin, D.J.9    Pettaway, C.A.10    Dinney, C.P.11
  • 13
    • 2442668068 scopus 로고    scopus 로고
    • A small interfering RNA targeting vascular endothelial growth factor as cancer therapeutics
    • Takei, Y.; Kadomatsu, K.; Yuzawa, Y.; Matsuo, S.; Muramatsu, T. A small interfering RNA targeting vascular endothelial growth factor as cancer therapeutics. Cancer Res. 2004, 64, 3365-3370.
    • (2004) Cancer Res. , vol.64 , pp. 3365-3370
    • Takei, Y.1    Kadomatsu, K.2    Yuzawa, Y.3    Matsuo, S.4    Muramatsu, T.5
  • 14
    • 1642295074 scopus 로고    scopus 로고
    • Development of vascular endothelial growth factor receptor (VEGFR) kinase inhibitors as anti-angiogenic agents in cancer therapy
    • Underiner, T. L.; Ruggeri, B.; Gingrich, D. E. Development of vascular endothelial growth factor receptor (VEGFR) kinase inhibitors as anti-angiogenic agents in cancer therapy. Cur. Med. Chem. 2004, 11, 731-745.
    • (2004) Cur. Med. Chem. , vol.11 , pp. 731-745
    • Underiner, T.L.1    Ruggeri, B.2    Gingrich, D.E.3
  • 15
    • 0036718947 scopus 로고    scopus 로고
    • Small molecule inhibitors of KDR (VEGFR-2) kinase: An overview of structure activity relationships
    • Boyer, S. J. Small molecule inhibitors of KDR (VEGFR-2) kinase: An overview of structure activity relationships. Curr. Top. Med. Chem. 2002, 2, 973-1000.
    • (2002) Curr. Top. Med. Chem. , vol.2 , pp. 973-1000
    • Boyer, S.J.1
  • 16
    • 0037232108 scopus 로고    scopus 로고
    • Small molecule tyrosine kinase inhibitors: Clinical development of anticancer agents
    • Laird, A. D.; Cherrington, J. M. Small molecule tyrosine kinase inhibitors: Clinical development of anticancer agents. Exp. Opin. Invest. Drugs 2003, 12, 51-64.
    • (2003) Exp. Opin. Invest. Drugs , vol.12 , pp. 51-64
    • Laird, A.D.1    Cherrington, J.M.2
  • 17
    • 7444222477 scopus 로고    scopus 로고
    • Expanded phase I/II study of PTK787/ZK 222584 (PTK/ZK), a novel, oral angiogenesis inhibitor, in combination with FOLFOX-4 as first-line treatment for patients with metastatic colorectal cancer
    • 2004 ASCO Annual Meeting Proceedings
    • Steward, W. P.; Thomas, A.; Morgan, B.; Wiedenmann, B.; Bartel, C.; Vanhoefer, U.; Trarbach, T.; Junker, U.; Laurent, D. Lebwohl, D. Expanded phase I/II study of PTK787/ZK 222584 (PTK/ZK), a novel, oral angiogenesis inhibitor, in combination with FOLFOX-4 as first-line treatment for patients with metastatic colorectal cancer. J. Clin. Oncol. (2004 ASCO Annual Meeting Proceedings) 2004, 22, 3556.
    • (2004) J. Clin. Oncol. , vol.22 , pp. 3556
    • Steward, W.P.1    Thomas, A.2    Morgan, B.3    Wiedenmann, B.4    Bartel, C.5    Vanhoefer, U.6    Trarbach, T.7    Junker, U.8    Laurent, D.9    Lebwohl, D.10
  • 18
    • 0141653352 scopus 로고    scopus 로고
    • Final results of a phase I and pharmacokinetic study of SU11248, a novel multi-target tyrosine kinase inhibitor, in patients with advanced cancers
    • abstr 769
    • Raymond, E.; Faivre, S.; Vera, K.; Delbaldo, C.; Robert, C.; Spatz, A.; Bello, C.; Brega, N.; Scigalla, P.; Armand, J. P. Final results of a phase I and pharmacokinetic study of SU11248, a novel multi-target tyrosine kinase inhibitor, in patients with advanced cancers. Proc. Am. Soc. Clin. Oncol. 2003, 22, 192 (abstr 769).
    • (2003) Proc. Am. Soc. Clin. Oncol. , vol.22 , pp. 192
    • Raymond, E.1    Faivre, S.2    Vera, K.3    Delbaldo, C.4    Robert, C.5    Spatz, A.6    Bello, C.7    Brega, N.8    Scigalla, P.9    Armand, J.P.10
  • 19
    • 0037208589 scopus 로고    scopus 로고
    • Phase II, randomized trial comparing bevacizumab plus fluorouracil (FU)/leucovorin (LV) with FU/LV alone in patients with metastatic colorectal cancer
    • Kabbinavar, F.; Hurwitz, H. I.; Fehrenbacher, L.; Meropol, N. J.; Novotny, W. F.; Lieberman, G.; Griffing, S.; Bergsland, E. Phase II, randomized trial comparing bevacizumab plus fluorouracil (FU)/leucovorin (LV) with FU/LV alone in patients with metastatic colorectal cancer [see comment]. J. Clin. Oncol. 2003, 21, 60-65.
    • (2003) J. Clin. Oncol. , vol.21 , pp. 60-65
    • Kabbinavar, F.1    Hurwitz, H.I.2    Fehrenbacher, L.3    Meropol, N.J.4    Novotny, W.F.5    Lieberman, G.6    Griffing, S.7    Bergsland, E.8
  • 28
    • 0034642482 scopus 로고    scopus 로고
    • Binding mode of the 4-anilinoquinazoline class of protein kinase inhibitor: X-ray crystallographic studies of 4-Anilinoquinazolines bound to cyclin-dependent kinase 2 and p38 kinase
    • Shewchuk, L.; Hassell, A.; Wisely, B.; Rocque, W.; Holmes, W.; Veal, J.; Kuyper, L. F. Binding Mode of the 4-Anilinoquinazoline Class of Protein Kinase Inhibitor: X-ray Crystallographic Studies of 4-Anilinoquinazolines Bound to Cyclin-Dependent Kinase 2 and p38 Kinase. J. Med. Chem. 2000, 43, 133-138.
    • (2000) J. Med. Chem. , vol.43 , pp. 133-138
    • Shewchuk, L.1    Hassell, A.2    Wisely, B.3    Rocque, W.4    Holmes, W.5    Veal, J.6    Kuyper, L.F.7
  • 29
    • 0141599428 scopus 로고    scopus 로고
    • Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-Anilinoquinazoline inhibitor
    • Stamos, J.; Sliwkowski, M. X.; Eigenbrot, C. Structure of the Epidermal Growth Factor Receptor Kinase Domain Alone and in Complex with a 4-Anilinoquinazoline Inhibitor. J. Biol. Chem. 2002, 277, 46265-46272.
    • (2002) J. Biol. Chem. , vol.277 , pp. 46265-46272
    • Stamos, J.1    Sliwkowski, M.X.2    Eigenbrot, C.3
  • 31
    • 0024377955 scopus 로고
    • Catechol-O-methyltransferase-inhibiting pyrocatechol derivatives: Synthesis and structure-activity studies
    • Borgulya, J.; Bruderer, H.; Bernauer, K.; Zuercher, G.; Mose, D.-P. Catechol-O-methyltransferase-inhibiting Pyrocatechol Derivatives: Synthesis and Structure-Activity Studies. Helv. Chim. Acta 1989, 72, 952-968.
    • (1989) Helv. Chim. Acta , vol.72 , pp. 952-968
    • Borgulya, J.1    Bruderer, H.2    Bernauer, K.3    Zuercher, G.4    Mose, D.-P.5
  • 32
    • 0037152415 scopus 로고    scopus 로고
    • Syntheses and EGFR and HER-2 kinase inhibitory activities of 4-Anilinoquinoline-3-carbonitriles. Analogues of three important 4-A-nilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents
    • Wissner, A.; Floyd, M. B; Rabindran, S. K.; Nilakantan, R.; Greenberger, L. M.; Shen, R.; Wang, Y.-F.; Tsou, H.-R. Syntheses and EGFR and HER-2 Kinase Inhibitory Activities of 4-Anilinoquinoline-3-Carbonitriles. Analogues of Three Important 4-A-nilinoquinazolines Currently Undergoing Clinical Evaluation as Therapeutic Antitumor Agents. Bioorg. Med. Chem. Lett. 2002, 12, 2893-2897.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2893-2897
    • Wissner, A.1    Floyd, M.B.2    Rabindran, S.K.3    Nilakantan, R.4    Greenberger, L.M.5    Shen, R.6    Wang, Y.-F.7    Tsou, H.-R.8
  • 33
    • 28144442373 scopus 로고    scopus 로고
    • Preparation of Aminoquinazolines Useful in the Treatment Of Cancer. Eur. Pat. Appl. EP602851, 1994
    • Barker, A. J.; Brown, D. S. Preparation of Aminoquinazolines Useful in the Treatment of Cancer. Eur. Pat. Appl. EP602851, 1994.
    • Barker, A.J.1    Brown, D.S.2
  • 34
    • 0034076822 scopus 로고    scopus 로고
    • Exploring the chemistry of quinones by computation
    • Magee, P. S. Exploring the Chemistry of Quinones by Computation. Quant. Struct. Act. Relat. 2000, 19, 22-28.
    • (2000) Quant. Struct. Act. Relat. , vol.19 , pp. 22-28
    • Magee, P.S.1
  • 35
    • 0001623290 scopus 로고
    • Frontier molecular Orbital Theory of substituent effects on regioselectivities of nucleophilic additions and cycloadditions to benzoquinones and naphthoquinones
    • Rozeboom, M. D.; Tegmo-Larsson, I.-M.; Houk, K. N. Frontier Molecular Orbital Theory of Substituent Effects on Regioselectivities of Nucleophilic Additions and Cycloadditions to Benzoquinones and Naphthoquinones. J. Org. Chem. 1981, 46, 2338-2345.
    • (1981) J. Org. Chem. , vol.46 , pp. 2338-2345
    • Rozeboom, M.D.1    Tegmo-Larsson, I.-M.2    Houk, K.N.3
  • 36
    • 0023100690 scopus 로고
    • Formation of glutathione-conjugated semiquinones by the reaction of quinones with glutathione: An ESR study
    • Takahashi, N.; Schreiber, J.; Fischer, V.; Mason, R. P. Formation of Glutathione-Conjugated Semiquinones by the Reaction of Quinones with Glutathione: An ESR Study. Arch. Biochem. Biophys. 1987, 252, 41-48.
    • (1987) Arch. Biochem. Biophys. , vol.252 , pp. 41-48
    • Takahashi, N.1    Schreiber, J.2    Fischer, V.3    Mason, R.P.4
  • 37
    • 28144461574 scopus 로고    scopus 로고
    • Santa Fe, NM
    • FRED; Open Eye Scientific Software: Santa Fe, NM (www.eyesopen.com)
    • FRED
  • 38
    • 28144447385 scopus 로고    scopus 로고
    • Solvation-based scoring for high throughput docking in virtual screening
    • Alvarez, J. and Shoichet, B., Eds.; CRC Press: Boca Raton, FL
    • Rush, T. S.; III.; Manas, E.; Tawa, G.; and Alvarez, J. Solvation-Based Scoring for High Throughput Docking in Virtual Screening in Drug Discovery; Alvarez, J. and Shoichet, B., Eds.; CRC Press: Boca Raton, FL, 2005; pp 241-269.
    • (2005) Drug Discovery , pp. 241-269
    • Rush III, T.S.1    Manas, E.2    Tawa, G.3    Alvarez, J.4
  • 39
    • 0012791813 scopus 로고    scopus 로고
    • A sensitive, time-resolved fluorometric assay for detection of inhibitors of phosphotyrosine kinases
    • Loganzo, F. and Hardy, C. A A Sensitive, Time-resolved Fluorometric Assay for Detection of Inhibitors of Phosphotyrosine Kinases. Am. Biotech. Lab. 1998, 16, 26-28.
    • (1998) Am. Biotech. Lab. , vol.16 , pp. 26-28
    • Loganzo, F.1    Hardy, C.A.2
  • 40
    • 0037075812 scopus 로고    scopus 로고
    • Novel 4-Anilinoquinazolines with C-7 basic side chains: Design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors
    • Hennequin, L. F.; Stokes, E. S. E.; Thomas, A. P.; Johnstone, C.; Ple, P. A.; Ogilvie, D. J.; Dukes, M.; Wedge, S. R.; Kendrew, J.; Curwen, J. O. Novel 4-Anilinoquinazolines with C-7 Basic Side Chains: Design and Structure Activity Relationship of a Series of Potent, Orally Active, VEGF Receptor Tyrosine Kinase Inhibitors. J. Med. Chem. 2002, 45, 1300-1312.
    • (2002) J. Med. Chem. , vol.45 , pp. 1300-1312
    • Hennequin, L.F.1    Stokes, E.S.E.2    Thomas, A.P.3    Johnstone, C.4    Ple, P.A.5    Ogilvie, D.J.6    Dukes, M.7    Wedge, S.R.8    Kendrew, J.9    Curwen, J.O.10
  • 42
    • 0033602091 scopus 로고    scopus 로고
    • Autophosphorylation of KDR in the kinase domain is required for maximal VEGF-stimulated kinase activity and receptor internalization
    • Dougher, M.; I. Terman, B. I. Autophosphorylation of KDR in the kinase domain is required for maximal VEGF-stimulated kinase activity and receptor internalization. Oncogene 1999, 18, 1619-1627.
    • (1999) Oncogene , vol.18 , pp. 1619-1627
    • Dougher, M.I.1    Terman, B.I.2
  • 43
    • 84891556199 scopus 로고    scopus 로고
    • Tripos, Inc : St. Louis, MO
    • Sybyl 6.9; Tripos, Inc : St. Louis, MO.
    • Sybyl 6.9
  • 44
    • 28144444278 scopus 로고    scopus 로고
    • Open Eye Scientific Software: Santa Fe, NM
    • OMEGA; Open Eye Scientific Software: Santa Fe, NM.
    • OMEGA
  • 47
    • 84981760233 scopus 로고
    • Preparation and conversions of 4,5,8-trihydroxy-6-mercaptoquinoline-2- carboxylic acid
    • Butenandt, A.; Biekert, E.; Haerle, E. Preparation and conversions of 4,5,8-trihydroxy-6-mercaptoquinoline-2-carboxylic acid. Chem. Ber. 1964, 97, 285-294.
    • (1964) Chem. Ber. , vol.97 , pp. 285-294
    • Butenandt, A.1    Biekert, E.2    Haerle, E.3


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