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Volumn 46, Issue 25, 2003, Pages 5375-5388

A New Class of Potent Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors: Structure-Activity Relationships for a Series of 9-Alkoxymethyl-12-(3-hydroxypropyl)indeno[2,1-a]pyrrolo[3,4-c]carbazole-5-ones and the Identification of CEP-5214 and Its Dimethylglycine Ester Prodrug Clinical Candidate CEP-7055

Author keywords

[No Author keywords available]

Indexed keywords

5,6,7,13 TETRAHYDRO 12 (3 HYDROXYPROPYL) 9 ISOPROPOXYMETHYLINDENO[2,1 A]PYRROLO[3,4 C]CARBAZOL 5(12H) ONE; 5,6,7,13 TETRAHYDRO 12 (3 HYDROXYPROPYL) 9 ISOPROPOXYMETHYLINDENO[2,1 A]PYRROLO[3,4 C]CARBAZOL 5(12H) ONE DIMETHYLGLYCINE ESTER; 9 METHYL 12 (3 HYDROXYPROPYL)INDENO[2,1 A]PYRROLO[3,4 C]CARBAZOL 5 ONE; ANGIOGENESIS INHIBITOR; ANGIOPOIETIN RECEPTOR; CARBAZOLE DERIVATIVE; CP 547 632; DIMETHYLGLYCINE ESTER; INEDENOPYRROLOCARBAZOLE; JANUS KINASE; PRODRUG; PROTEIN CDK1; PROTEIN KINASE C; PROTEIN SERINE THREONINE KINASE; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE A; PROTEIN TYROSINE KINASE INHIBITOR; SUNITINIB; SYNAPTOPHYSIN; UNCLASSIFIED DRUG; VANDETANIB; VASCULOTROPIN RECEPTOR TYROSINE KINASE INHIBITOR; VATALANIB;

EID: 10744227153     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0301641     Document Type: Article
Times cited : (88)

References (48)
  • 1
    • 0035211504 scopus 로고    scopus 로고
    • Angiogenesis-dependent diseases
    • Folkman, J. Angiogenesis-dependent diseases. Semin. Oncol. 2001, 28, 536-542.
    • (2001) Semin. Oncol. , vol.28 , pp. 536-542
    • Folkman, J.1
  • 2
    • 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
    • 0034090097 scopus 로고    scopus 로고
    • Angiogenesis: Potentials for pharmacologic intervention in the treatment of cancer, cardiovascular diseases, and chronic inflammation
    • Griffloen, A. W.; Molema, G. Angiogenesis: potentials for pharmacologic intervention in the treatment of cancer, cardiovascular diseases, and chronic inflammation. Pharmacol. Rev. 2000, 52, 237-268.
    • (2000) Pharmacol. Rev. , vol.52 , pp. 237-268
    • Griffloen, A.W.1    Molema, G.2
  • 4
    • 0028929803 scopus 로고
    • Angiogenesis in cancer, vascular, rheumatoid and other disease
    • Folkman, J. Angiogenesis in cancer, vascular, rheumatoid and other disease. Nat. Med. 1995, 1, 27-31.
    • (1995) Nat. Med. , vol.1 , pp. 27-31
    • Folkman, J.1
  • 5
    • 0028912119 scopus 로고
    • Controlling the vasculature: Angiogenesis, anti-angiogenesis, and vascular targeting of gene therapy
    • Fan, T. P. D.; Jaggar, R.; Bicknell, R. Controlling the vasculature: angiogenesis, anti-angiogenesis, and vascular targeting of gene therapy. Trends Pharmacol. Sci. 1995, 16, 57-66.
    • (1995) Trends Pharmacol. Sci. , vol.16 , pp. 57-66
    • Fan, T.P.D.1    Jaggar, R.2    Bicknell, R.3
  • 6
    • 0030791178 scopus 로고    scopus 로고
    • Receptor tyrosine kinase as targets for inhibition of angiogenesis
    • Gimbrone, M. Receptor tyrosine kinase as targets for inhibition of angiogenesis. Drug Discovery Today 1997, 2, 50-63.
    • (1997) Drug Discovery Today , vol.2 , pp. 50-63
    • Gimbrone, M.1
  • 7
    • 0030044984 scopus 로고    scopus 로고
    • Vascular endothelial growth factor, a potent and selective angiogenic agent
    • (a) Thomas, K. A. Vascular endothelial growth factor, a potent and selective angiogenic agent. J. Biol. Chem. 1996, 271, 603-606.
    • (1996) J. Biol. Chem. , vol.271 , pp. 603-606
    • Thomas, K.A.1
  • 8
    • 0031039243 scopus 로고    scopus 로고
    • The biology of vascular endothelial growth factor
    • (b) Ferrara, N.; Davis-Smyth, T. The biology of vascular endothelial growth factor. Endocr. Rev. 1997, 18, 4-25.
    • (1997) Endocr. Rev. , vol.18 , pp. 4-25
    • Ferrara, N.1    Davis-Smyth, T.2
  • 10
    • 0030829035 scopus 로고    scopus 로고
    • Enhanced expression of vascular endothelial growth factor in metastatic melanoma
    • (a) Salvern, P.; Heikkila, P.; Joensuu, H. Enhanced expression of vascular endothelial growth factor in metastatic melanoma. Br. J. Cancer 1997, 76, 930-934.
    • (1997) Br. J. Cancer , vol.76 , pp. 930-934
    • Salvern, P.1    Heikkila, P.2    Joensuu, H.3
  • 11
    • 0031779403 scopus 로고
    • Tumour angiogenesis and vascular endothelial growth factor expression in stage I lung adrenocarcinoma
    • (b) Shibusa, T.; Shijubo, N.; Abe, S. Tumour angiogenesis and vascular endothelial growth factor expression in stage I lung adrenocarcinoma. Clin. Cancer Res. 1944, 4, 1483-1487.
    • (1944) Clin. Cancer Res. , vol.4 , pp. 1483-1487
    • Shibusa, T.1    Shijubo, N.2    Abe, S.3
  • 12
    • 0031955262 scopus 로고    scopus 로고
    • Expression of vascular endothelial growth factor correlates with tumour progression in gallbladder cancer clinical studies
    • (c) Okita, S.; Kondoh, S.; Shiraishi, K.; Kaino, S.; Hatano, S.; Okita, K. Expression of vascular endothelial growth factor correlates with tumour progression in gallbladder cancer clinical studies. Int. J. Oncol. 1998, 12, 1013-1018.
    • (1998) Int. J. Oncol. , vol.12 , pp. 1013-1018
    • Okita, S.1    Kondoh, S.2    Shiraishi, K.3    Kaino, S.4    Hatano, S.5    Okita, K.6
  • 13
    • 0031941942 scopus 로고    scopus 로고
    • Vascular endothelial growth factor expression and vascular density as prognostic markers of survival in patients with low grade astrocytoma
    • (d) Abdulrauf, S. I. Edvardsen, K.; Ho, K. L.; Yang, X. Y.; Rock, J. P.; Rosenblum, M. L. Vascular endothelial growth factor expression and vascular density as prognostic markers of survival in patients with low grade astrocytoma. J. Neurosurg. 1998, 88, 513-520.
    • (1998) J. Neurosurg. , vol.88 , pp. 513-520
    • Abdulrauf, S.I.1    Edvardsen, K.2    Ho, K.L.3    Yang, X.Y.4    Rock, J.P.5    Rosenblum, M.L.6
  • 14
    • 0032907687 scopus 로고    scopus 로고
    • Vascular endothelial growth factor (VEGF) and its receptors
    • Neufeld, G.; Cohen, T.; Gengrinovitch, S.; Poltorak, Z. Vascular endothelial growth factor (VEGF) and its receptors. FASEB J. 1999, 13, 9-22.
    • (1999) FASEB J. , vol.13 , pp. 9-22
    • Neufeld, G.1    Cohen, T.2    Gengrinovitch, S.3    Poltorak, Z.4
  • 15
    • 0034595635 scopus 로고    scopus 로고
    • Receptor chimeras indicate that the vascular endothelial growth factor receptor-1 modulates mitogenic activity of VEGF-R2 in endothelial cells
    • Rahim, N.; Dayanir, V.; Lashkari, K. Receptor chimeras indicate that the vascular endothelial growth factor receptor-1 modulates mitogenic activity of VEGF-R2 in endothelial cells. J. Biol. Chem. 2000, 275, 16986-16992.
    • (2000) J. Biol. Chem. , vol.275 , pp. 16986-16992
    • Rahim, N.1    Dayanir, V.2    Lashkari, K.3
  • 17
    • 0032053767 scopus 로고    scopus 로고
    • Signaling angiogenesis and lymphangiogenesis
    • (a) Korpelainen, E. I.; Alitalo, K. Signaling angiogenesis and lymphangiogenesis. Curr. Opin. Cell Biol. 1998, 10, 159-164.
    • (1998) Curr. Opin. Cell Biol. , vol.10 , pp. 159-164
    • Korpelainen, E.I.1    Alitalo, K.2
  • 18
    • 0030453355 scopus 로고    scopus 로고
    • VEGF-C receptor binding and pattern of expression with VEGF-R3 suggests a role in lymphatic vascular development
    • (b) Kukk, E.; Lymboussaki, A.; Taira, S.; Kaipainen, A.; Jeltsch, M.; Joukov, V.; Alitalo, K. VEGF-C receptor binding and pattern of expression with VEGF-R3 suggests a role in lymphatic vascular development. Development 1996, 122, 3829-3837.
    • (1996) Development , vol.122 , pp. 3829-3837
    • Kukk, E.1    Lymboussaki, A.2    Taira, S.3    Kaipainen, A.4    Jeltsch, M.5    Joukov, V.6    Alitalo, K.7
  • 19
    • 0001123485 scopus 로고    scopus 로고
    • Holland, J. E., Frei, I. E., Bast, J., Kufe, D., Pollock, R., Weichselbaum, R., Eds.; B. C. Dekker, Inc.: Ontario, Canada
    • Folkman, J. In Cancer Medicine, 5th ed.; Holland, J. E., Frei, I. E., Bast, J., Kufe, D., Pollock, R., Weichselbaum, R., Eds.; B. C. Dekker, Inc.: Ontario, Canada, 2000; pp 132-152.
    • (2000) Cancer Medicine, 5th Ed. , pp. 132-152
    • Folkman, J.1
  • 20
    • 0033853171 scopus 로고    scopus 로고
    • Anti-angiogenic agents: Clinical trial design and therapies in development
    • (a) Deplanque, G.; Harris, A. L. Anti-angiogenic agents: clinical trial design and therapies in development. Eur. J. Cancer 2000, 36, 1713-1724.
    • (2000) Eur. J. Cancer , vol.36 , pp. 1713-1724
    • Deplanque, G.1    Harris, A.L.2
  • 23
    • 0034256094 scopus 로고    scopus 로고
    • Inhibition of tumor angiogenesis by synthetic receptor tyrosine kinase inhibitors
    • Sun, L.; McMahon, G. Inhibition of tumor angiogenesis by synthetic receptor tyrosine kinase inhibitors. Drug Discovery Today 2000, 5, 344-354.
    • (2000) Drug Discovery Today , vol.5 , pp. 344-354
    • Sun, L.1    McMahon, G.2
  • 24
    • 0037099598 scopus 로고    scopus 로고
    • PTK787/ZK222584, a specific vascular endothelial growth factor-receptor tyrosine kinase inhibitor, effects the anatomy of the tumor vascular bed and the functional vascular properties as detected by dynamic enhanced magnetic resonance imaging
    • (a) Drevs, J.; Muller-Driver, R.; Wittig, C.; Fuxius, S.; Esser, N.; Hugenschmidt, H.; Konerding, M. A.; Allegrini, P. R.; Wood, J.; Hennig, J.; Unger, C.; Marine, D. PTK787/ZK222584, a specific vascular endothelial growth factor-receptor tyrosine kinase inhibitor, effects the anatomy of the tumor vascular bed and the functional vascular properties as detected by dynamic enhanced magnetic resonance imaging. Cancer Res. 2002, 62, 4015-4022.
    • (2002) Cancer Res. , vol.62 , pp. 4015-4022
    • Drevs, J.1    Muller-Driver, R.2    Wittig, C.3    Fuxius, S.4    Esser, N.5    Hugenschmidt, H.6    Konerding, M.A.7    Allegrini, P.R.8    Wood, J.9    Hennig, J.10    Unger, C.11    Marine, D.12
  • 25
    • 0036531923 scopus 로고    scopus 로고
    • Blockade of vascular endothelial growth factor receptor and epidermal growth factor receptor signaling for therapy of metastatic human pancreatic cancer
    • (b) Baker, C. H.; Solorzano, C. C.; Fidler, I. J. Blockade of vascular endothelial growth factor receptor and epidermal growth factor receptor signaling for therapy of metastatic human pancreatic cancer. Cancer Res. 2002, 62, 1996-2003.
    • (2002) Cancer Res. , vol.62 , pp. 1996-2003
    • Baker, C.H.1    Solorzano, C.C.2    Fidler, I.J.3
  • 27
    • 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
    • (a) Hennequin, L. F.; Stokes, E. S.; 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.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
  • 30
    • 0345655596 scopus 로고    scopus 로고
    • Selected fused pyrrolocarbazoles. Patent WO 0217914, 2002
    • (a) Gingrich, D. E.; Hudkins, R. L. Selected fused pyrrolocarbazoles. Patent WO 0217914, 2002.
    • Gingrich, D.E.1    Hudkins, R.L.2
  • 31
    • 0141521943 scopus 로고    scopus 로고
    • CEP-5214, a novel orally-active inhibitor of vascular endothelial growth factor (VEGF) receptor tyrosine kinases, inhibits VEGF-induced angiogenesis and prostate tumor growth in vivo
    • (b) Pili, R.; Robinson, C.; Morris, C. A.; Dionne, C. A.; Isaacs, J. T.; Ruggeri, B. A. CEP-5214, a novel orally-active inhibitor of vascular endothelial growth factor (VEGF) receptor tyrosine kinases, inhibits VEGF-induced angiogenesis and prostate tumor growth in vivo. Clin. Cancer Res. 2001, 7, 3658s.
    • (2001) Clin. Cancer Res. , vol.7
    • Pili, R.1    Robinson, C.2    Morris, C.A.3    Dionne, C.A.4    Isaacs, J.T.5    Ruggeri, B.A.6
  • 32
    • 0345223763 scopus 로고    scopus 로고
    • Fused pyrrolocarbazole. U.S. Patent 5,705,511, 1997
    • Hudkins, R. L.; Knight, E., Jr. Fused pyrrolocarbazole. U.S. Patent 5,705,511, 1997.
    • Hudkins, R.L.1    Knight Jr., E.2
  • 33
    • 0037285267 scopus 로고    scopus 로고
    • Synthesis of indeno[2,1-a]pyrrolo-[3,4-c]carbazole lactam regioisomers using ethyl cis-β-cyanoacrylate as a dienophile and lactam precursor
    • Hudkins, R. L.; Park, C.-H. Synthesis of indeno[2,1-a]pyrrolo-[3,4-c]carbazole lactam regioisomers using ethyl cis-β-cyanoacrylate as a dienophile and lactam precursor. J. Heterocycl. Chem. 2003, 40, 135-142.
    • (2003) J. Heterocycl. Chem. , vol.40 , pp. 135-142
    • Hudkins, R.L.1    Park, C.-H.2
  • 35
    • 0344792908 scopus 로고
    • Synthesis of esters
    • Colquhoun, H. M., Thompson, D. J., Twigg, M. V., Eds.; Plenum Press: New York
    • Synthesis of esters. In Carbonylation: Direct Synthesis of Carbonyl Compounds; Colquhoun, H. M., Thompson, D. J., Twigg, M. V., Eds.; Plenum Press: New York, 1991; pp 111-141.
    • (1991) Carbonylation: Direct Synthesis of Carbonyl Compounds , pp. 111-141
  • 37
    • 0030945871 scopus 로고    scopus 로고
    • Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors
    • Mohammadi, M.; McMahon, G.; Sun, L.; Tang, C.; Hirth, P.; Yeh, B. K.; Hubbard, S. R.; Schlessinger, J. Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors. Science 1997, 276, 955-960.
    • (1997) Science , vol.276 , pp. 955-960
    • Mohammadi, M.1    McMahon, G.2    Sun, L.3    Tang, C.4    Hirth, P.5    Yeh, B.K.6    Hubbard, S.R.7    Schlessinger, J.8
  • 39
    • 0031574375 scopus 로고    scopus 로고
    • Structures of staurosporine bound to CDK2 and cPKA-new tools for structure-based design of protein kinase inhibitors
    • Toledo, L. M.; Lydon, N. B. Structures of staurosporine bound to CDK2 and cPKA-new tools for structure-based design of protein kinase inhibitors. Curr. Biol. 1997, 5, 1551-1556.
    • (1997) Curr. Biol. , vol.5 , pp. 1551-1556
    • Toledo, L.M.1    Lydon, N.B.2
  • 42
    • 0035044630 scopus 로고    scopus 로고
    • In vitro models of vasculogenesis and angiogenesis
    • (a) Vailhe, B.; Vittet, D.; Feige, J.-J. In vitro models of vasculogenesis and angiogenesis. Lab. Invest. 2001, 81, 439-452.
    • (2001) Lab. Invest. , vol.81 , pp. 439-452
    • Vailhe, B.1    Vittet, D.2    Feige, J.-J.3
  • 43
    • 0032440723 scopus 로고    scopus 로고
    • Distinct signal transduction pathways are utilized during the tube formation and survival phases of in vitro angiogenesis
    • (b) Ilan, N.; Mahooti, S.; Madri, J. A. Distinct signal transduction pathways are utilized during the tube formation and survival phases of in vitro angiogenesis. J. Cell Sci. 1998, 111, 3621-3631.
    • (1998) J. Cell Sci. , vol.111 , pp. 3621-3631
    • Ilan, N.1    Mahooti, S.2    Madri, J.A.3
  • 45
    • 0030698296 scopus 로고    scopus 로고
    • Endogenous regulation of angiogenesis in the rat aorta model. Role of vascular endothelial growth factor
    • (d) Nicosia, R. F.; Lin, Y. J.; Hazelton, D.; Qian, X. Endogenous regulation of angiogenesis in the rat aorta model. Role of vascular endothelial growth factor. Am. J. Pathol. 1997, 151, 1379-1386.
    • (1997) Am. J. Pathol. , vol.151 , pp. 1379-1386
    • Nicosia, R.F.1    Lin, Y.J.2    Hazelton, D.3    Qian, X.4
  • 47
    • 0036152493 scopus 로고    scopus 로고
    • The chemopreventive agent Olipraz possesses potent antiangiogenic activity in vitro, ex vivo, and in vivo and inhibits tumor xenograph growth
    • Ruggeri, B. A.; Robinson, C.; Angeles, T.; Wilkinson, J.; Clapper, M. L. The chemopreventive agent Olipraz possesses potent antiangiogenic activity in vitro, ex vivo, and in vivo and inhibits tumor xenograph growth. Clin. Cancer Res. 2002, 8, 267-274.
    • (2002) Clin. Cancer Res. , vol.8 , pp. 267-274
    • Ruggeri, B.A.1    Robinson, C.2    Angeles, T.3    Wilkinson, J.4    Clapper, M.L.5
  • 48
    • 0026567491 scopus 로고
    • SH2 domains prevent tyrosine dephosphorylation of the EGF receptor: Identification of Tyr992 as the high-affinity binding site for SH2 domains of phospholipase C-γ
    • Rotin, D.; Margolis, B.; Mohammadi, M.; Daly, R. J.; Daum, G.; Li, N.; Fischer, E. F.; Burgess, W. H.; Ullrich, A.; Schlessinger, J. SH2 domains prevent tyrosine dephosphorylation of the EGF receptor: identification of Tyr992 as the high-affinity binding site for SH2 domains of phospholipase C-γ. EMBO J. 1992, 11, 559-567.
    • (1992) EMBO J. , vol.11 , pp. 559-567
    • Rotin, D.1    Margolis, B.2    Mohammadi, M.3    Daly, R.J.4    Daum, G.5    Li, N.6    Fischer, E.F.7    Burgess, W.H.8    Ullrich, A.9    Schlessinger, J.10


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