메뉴 건너뛰기




Volumn 49, Issue 26, 2006, Pages 7868-7876

Synthesis and Src kinase inhibitory activity of a series of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-furyl-3-quinolinecarbonitriles

Author keywords

[No Author keywords available]

Indexed keywords

4 [(2,4 DICHLORO 5 METHOXYPHENYL)AMINO] 6 METHOXY 7 [5 [(4 METHYLPIPERAZIN 1 YL)METHYL] 3 FURYL] 3 QUINOLINECARBONITRILE; ABELSON KINASE; BOSUTINIB; DASATINIB; IMATINIB; PROTEIN KINASE LCK; UNCLASSIFIED DRUG;

EID: 33845962586     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061031t     Document Type: Article
Times cited : (34)

References (37)
  • 1
    • 7944231535 scopus 로고    scopus 로고
    • The road to Src
    • Martin, G. S. The road to Src. Oncogene 2004, 23, 7910-7917.
    • (2004) Oncogene , vol.23 , pp. 7910-7917
    • Martin, G.S.1
  • 2
    • 7944236785 scopus 로고    scopus 로고
    • Src family kinases, key regulators of signal transduction
    • Parsons, S. J.; Parsons, J. T. Src family kinases, key regulators of signal transduction. Oncogene 2004, 23, 7906-7909.
    • (2004) Oncogene , vol.23 , pp. 7906-7909
    • Parsons, S.J.1    Parsons, J.T.2
  • 3
    • 33645072205 scopus 로고    scopus 로고
    • Treatment for advanced tumors: SRC reclaims center stage
    • Summy, J. M.; Gallick, G. E. Treatment for advanced tumors: SRC reclaims center stage. Clin. Cancer Res. 2006, 12, 1398-1401.
    • (2006) Clin. Cancer Res , vol.12 , pp. 1398-1401
    • Summy, J.M.1    Gallick, G.E.2
  • 4
    • 33646232229 scopus 로고    scopus 로고
    • Src tyrosine kinase as a chemotherapeutic target: Is there a clinical case?
    • Chen, T.; George, J. A.; Taylor, C. C. Src tyrosine kinase as a chemotherapeutic target: is there a clinical case? Anti-Cancer Drugs 2006, 17, 123-131.
    • (2006) Anti-Cancer Drugs , vol.17 , pp. 123-131
    • Chen, T.1    George, J.A.2    Taylor, C.C.3
  • 5
    • 0038386613 scopus 로고    scopus 로고
    • Src family kinases in tumor progression and metastasis
    • Summy, J. M.; Gallick, G. E. Src family kinases in tumor progression and metastasis. Cancer Metastasis Rev. 2003, 22, 337-358.
    • (2003) Cancer Metastasis Rev , vol.22 , pp. 337-358
    • Summy, J.M.1    Gallick, G.E.2
  • 7
    • 7244247062 scopus 로고    scopus 로고
    • Endothelial barrier disruption by VEGF-mediated Src activity potentiates tumor cell extravasation and metastasis
    • Weis, S.; Cui, J.; Barnes, L.; Cheresh, D. Endothelial barrier disruption by VEGF-mediated Src activity potentiates tumor cell extravasation and metastasis. J. Cell Biol. 2004, 167, 223-229.
    • (2004) J. Cell Biol , vol.167 , pp. 223-229
    • Weis, S.1    Cui, J.2    Barnes, L.3    Cheresh, D.4
  • 8
    • 13544252467 scopus 로고    scopus 로고
    • Tumor metastasis but not tumor growth is dependent on Src-mediated vascular permeability
    • Criscuoli, M. L.; Nguyen, M.; Eliceiri, B. P. Tumor metastasis but not tumor growth is dependent on Src-mediated vascular permeability. Blood 2005, 105, 1508-1514.
    • (2005) Blood , vol.105 , pp. 1508-1514
    • Criscuoli, M.L.1    Nguyen, M.2    Eliceiri, B.P.3
  • 10
    • 33644647192 scopus 로고    scopus 로고
    • Inhibition of SRC expression and activity inhibits tumor progression and metastasis of human pancreatic adenocarcinoma cells in an orthotopic nude mouse model
    • Trevino, J. G.; Summy, J. M.; Lesslie, D. P.; Parikh, N. U.; Hong, D. S.; Lee, F. Y.; Donato, N. J.; Abbruzzese, J. L.; Baker, C. H.; Gallick, G. E. Inhibition of SRC expression and activity inhibits tumor progression and metastasis of human pancreatic adenocarcinoma cells in an orthotopic nude mouse model. Am. J. Pathol. 2006, 168, 962-972.
    • (2006) Am. J. Pathol , vol.168 , pp. 962-972
    • Trevino, J.G.1    Summy, J.M.2    Lesslie, D.P.3    Parikh, N.U.4    Hong, D.S.5    Lee, F.Y.6    Donato, N.J.7    Abbruzzese, J.L.8    Baker, C.H.9    Gallick, G.E.10
  • 11
    • 0035992434 scopus 로고    scopus 로고
    • Src family kinase inhibitor PP2 restores the E-cadherin/catenin cell adhesion system in human cancer cells and reduces cancer metastasis
    • Nam, J. S.; Ino, Y.; Sakamoto, M.; Hirohashi, S. Src family kinase inhibitor PP2 restores the E-cadherin/catenin cell adhesion system in human cancer cells and reduces cancer metastasis. Clin. Cancer Res. 2002, 8, 2430-2436.
    • (2002) Clin. Cancer Res , vol.8 , pp. 2430-2436
    • Nam, J.S.1    Ino, Y.2    Sakamoto, M.3    Hirohashi, S.4
  • 12
    • 30344460024 scopus 로고    scopus 로고
    • AP23846, a novel and highly potent Src family kinase inhibitor, reduces vascular endothelial growth factor and interleukin-8 expression in human solid tumor cell lines and abrogates downstream angiogenic processes
    • Summy, J. M.; Trevino, J. G.; Lesslie, D. P.; Baker, C. H.; Shakespeare, W. C.; Wang, Y.; Sundaramoorthi, R.; Metcalf, C. A., III; Keats, J. A.; Sawyer, T. K.; Gallick, G. E. AP23846, a novel and highly potent Src family kinase inhibitor, reduces vascular endothelial growth factor and interleukin-8 expression in human solid tumor cell lines and abrogates downstream angiogenic processes. Mol. Cancer Ther. 2005, 4, 1900-1911.
    • (2005) Mol. Cancer Ther , vol.4 , pp. 1900-1911
    • Summy, J.M.1    Trevino, J.G.2    Lesslie, D.P.3    Baker, C.H.4    Shakespeare, W.C.5    Wang, Y.6    Sundaramoorthi, R.7    Metcalf III, C.A.8    Keats, J.A.9    Sawyer, T.K.10    Gallick, G.E.11
  • 13
    • 33745402375 scopus 로고    scopus 로고
    • Elevated Src activity promotes cellular invasion and motility in tamoxifen resistant breast cancer cells
    • Hiscox, S.; Morgan, L.; Green, T. P.; Barrow, D.; Gee, J.; Nicholson, R. I. Elevated Src activity promotes cellular invasion and motility in tamoxifen resistant breast cancer cells. Breast Cancer Res. Treat. 2006, 97, 263-274.
    • (2006) Breast Cancer Res. Treat , vol.97 , pp. 263-274
    • Hiscox, S.1    Morgan, L.2    Green, T.P.3    Barrow, D.4    Gee, J.5    Nicholson, R.I.6
  • 14
    • 24744432879 scopus 로고    scopus 로고
    • Src tyrosine kinase inhibitor, M475271, suppresses subcutaneous growth and production of lung metastasis via inhibition of proliferation, invasion, and vascularization of human lung adenocarcinoma cells
    • Zheng, R.; Yano, S.; Matsumori, Y.; Nakataki, E.; Muguruma, H.; Yoshizumi, M.; Sone, S. Src tyrosine kinase inhibitor, M475271, suppresses subcutaneous growth and production of lung metastasis via inhibition of proliferation, invasion, and vascularization of human lung adenocarcinoma cells. Clin. Exp. Metastasis 2005, 22, 195-204.
    • (2005) Clin. Exp. Metastasis , vol.22 , pp. 195-204
    • Zheng, R.1    Yano, S.2    Matsumori, Y.3    Nakataki, E.4    Muguruma, H.5    Yoshizumi, M.6    Sone, S.7
  • 16
    • 18844397942 scopus 로고    scopus 로고
    • Dual inhibitors of Src and Abl tyrosine kinases
    • Boschelli, D. H. Dual inhibitors of Src and Abl tyrosine kinases. Drug Des. Rev.-Online 2004, 1, 203-214.
    • (2004) Drug Des. Rev.-Online , vol.1 , pp. 203-214
    • Boschelli, D.H.1
  • 17
    • 27244437924 scopus 로고    scopus 로고
    • New targeted approaches in chronic myeloid leukemia
    • Cortes, J.; Kantarjian, H. New targeted approaches in chronic myeloid leukemia. J. Clin. Oncol. 2005, 23, 6316-6324.
    • (2005) J. Clin. Oncol , vol.23 , pp. 6316-6324
    • Cortes, J.1    Kantarjian, H.2
  • 18
    • 29144464371 scopus 로고    scopus 로고
    • Advances in the structural biology, design and clinical development of Bcr-Abl kinase inhibitors for the treatment of chronic myeloid leukaemia
    • Manley, P. W.; Cowan-Jacob, S. W.; Mestan, J. Advances in the structural biology, design and clinical development of Bcr-Abl kinase inhibitors for the treatment of chronic myeloid leukaemia. Biochim. Biophys. Acta 2005, 1754, 3-13.
    • (2005) Biochim. Biophys. Acta , vol.1754 , pp. 3-13
    • Manley, P.W.1    Cowan-Jacob, S.W.2    Mestan, J.3
  • 19
    • 27644566271 scopus 로고    scopus 로고
    • Dual tyrosine kinase inhibitors in chronic myeloid leukemia
    • Martinelli, G.; Soverini, S.; Rosti, G.; Baccarani, M. Dual tyrosine kinase inhibitors in chronic myeloid leukemia. Leukemia 2005, 19, 1872-1879.
    • (2005) Leukemia , vol.19 , pp. 1872-1879
    • Martinelli, G.1    Soverini, S.2    Rosti, G.3    Baccarani, M.4
  • 20
    • 3142676436 scopus 로고    scopus 로고
    • Overriding Imatinib resistance with a novel ABL kinase inhibitor
    • Shah, N. P.; Tran, C.; Lee, F. Y.; Chen, P.; Morris, D.; Sawyers, C. L. Overriding Imatinib resistance with a novel ABL kinase inhibitor. Science 2004, 305, 399-402.
    • (2004) Science , vol.305 , pp. 399-402
    • Shah, N.P.1    Tran, C.2    Lee, F.Y.3    Chen, P.4    Morris, D.5    Sawyers, C.L.6
  • 21
    • 19944428353 scopus 로고    scopus 로고
    • Lombardo, L. J.; Lee, F. Y.; Chen, P.; Norris, D.; Baish, J. C.; Behnia, K.; Castaneda, S.; Cornelius, L. A. M.; Das, J.; Doweyko, A. M.; Fairchild, C.; Hunt, J. T.; Inigo, I.; Johnston, K.; Kamath, A.; Kan, D.; Klei, H.; Marathe, P.; Pang, S.; Peterson, R.; Pitt, S.; Schieven, G. L.; Schmidt, R. J.; Tokarski, J.; Wen, M.-L.; Wityak, J.; Borzilleri, R. M. Discovery of N-(2-chloro- 6-methyl-phenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-1-yl)-2-methylpyrimidin-4- ylamino)thiazole-5-carboxamide (BMS-354825), a dual Src/Abl kinase inhibitor with potent antitumor activity in preclinical assays. J. Med. Chem. 2004, 47, 6658-6661.
    • Lombardo, L. J.; Lee, F. Y.; Chen, P.; Norris, D.; Baish, J. C.; Behnia, K.; Castaneda, S.; Cornelius, L. A. M.; Das, J.; Doweyko, A. M.; Fairchild, C.; Hunt, J. T.; Inigo, I.; Johnston, K.; Kamath, A.; Kan, D.; Klei, H.; Marathe, P.; Pang, S.; Peterson, R.; Pitt, S.; Schieven, G. L.; Schmidt, R. J.; Tokarski, J.; Wen, M.-L.; Wityak, J.; Borzilleri, R. M. Discovery of N-(2-chloro- 6-methyl-phenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-1-yl)-2-methylpyrimidin-4- ylamino)thiazole-5-carboxamide (BMS-354825), a dual Src/Abl kinase inhibitor with potent antitumor activity in preclinical assays. J. Med. Chem. 2004, 47, 6658-6661.
  • 25
    • 0037439689 scopus 로고    scopus 로고
    • SKI-606, a 4-anilino-3-quinolinecarbonitrile dual inhibitor of Src and Abl kinases, is a potent antiproliferative agent against chronic myelogenous leukemia cells in culture and causes regression of K562 xenografts in nude mice
    • Golas, J. M.; Arndt, K.; Etienne, C.; Lucas, J.; Nardin, D.; Gibbons, J.; Frost, P.; Ye, F.; Boschelli, D. H.; Boschelli, F. SKI-606, a 4-anilino-3-quinolinecarbonitrile dual inhibitor of Src and Abl kinases, is a potent antiproliferative agent against chronic myelogenous leukemia cells in culture and causes regression of K562 xenografts in nude mice. Cancer Res. 2003, 63, 375-381.
    • (2003) Cancer Res , vol.63 , pp. 375-381
    • Golas, J.M.1    Arndt, K.2    Etienne, C.3    Lucas, J.4    Nardin, D.5    Gibbons, J.6    Frost, P.7    Ye, F.8    Boschelli, D.H.9    Boschelli, F.10
  • 27
    • 33644532202 scopus 로고    scopus 로고
    • SKI-606 decreases growth and motility of colorectal cancer cells by preventing pp60(c-Src)-dependent tyrosine phosphorylation of β-catenin and its nuclear signaling
    • Coluccia, A. M. L.; Benati, D.; Dekhil, H.; De Filippo, A.; Lan, C.; Gambacorti-Passerini, C. SKI-606 decreases growth and motility of colorectal cancer cells by preventing pp60(c-Src)-dependent tyrosine phosphorylation of β-catenin and its nuclear signaling. Cancer Res. 2006, 66, 2279-2286.
    • (2006) Cancer Res , vol.66 , pp. 2279-2286
    • Coluccia, A.M.L.1    Benati, D.2    Dekhil, H.3    De Filippo, A.4    Lan, C.5    Gambacorti-Passerini, C.6
  • 30
    • 37049081803 scopus 로고
    • Oxidative substitution reactions of organotin compounds with lead tetraacetate
    • Yamamoto, M.; Izukawa, H.; Saiki, M.; Yamada, K. Oxidative substitution reactions of organotin compounds with lead tetraacetate. J. Chem. Soc., Chem. Commun. 1988, 8, 560-561.
    • (1988) J. Chem. Soc., Chem. Commun , vol.8 , pp. 560-561
    • Yamamoto, M.1    Izukawa, H.2    Saiki, M.3    Yamada, K.4
  • 31
    • 33845945984 scopus 로고    scopus 로고
    • Sutherland, K. W, Feigelson, G. B, Boschelli, D. H, Blum, D. M, Strong, H. L. Process for the preparation of 4-amino-3-quinolinecarbonitriles and 7-aminothieno[3,2-b]pyridine-6-carbonitriles, US 2005043537, 2005
    • Sutherland, K. W.; Feigelson, G. B.; Boschelli, D. H.; Blum, D. M.; Strong, H. L. Process for the preparation of 4-amino-3-quinolinecarbonitriles and 7-aminothieno[3,2-b]pyridine-6-carbonitriles, US 2005043537, 2005.
  • 32
    • 14644413418 scopus 로고    scopus 로고
    • Further studies on ethenyl and ethynyl-4-phenylamino-3-quinolinecarbonitriles: Identification of a subnanomolar Src kinase inhibitor
    • Barrios Sosa, A. C.; Boschelli, D. H.; Wu, B.; Wang, Y.; Golas, J. M. Further studies on ethenyl and ethynyl-4-phenylamino-3-quinolinecarbonitriles: Identification of a subnanomolar Src kinase inhibitor. Bioorg. Med. Chem. Lett. 2005, 15, 1743-1747.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 1743-1747
    • Barrios Sosa, A.C.1    Boschelli, D.H.2    Wu, B.3    Wang, Y.4    Golas, J.M.5
  • 33
    • 1842690156 scopus 로고    scopus 로고
    • Synthesis and inhibition of Src kinase activity by 7-ethenyl and 7-ethynyl-4-anilino-3-quinolinecarbonitriles
    • Barrios Sosa, A. C.; Boschelli, D. H.; Ye, F.; Golas, J. M.; Boschelli, F. Synthesis and inhibition of Src kinase activity by 7-ethenyl and 7-ethynyl-4-anilino-3-quinolinecarbonitriles. Bioorg. Med. Chem. Lett. 2004, 14, 2155-2158.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 2155-2158
    • Barrios Sosa, A.C.1    Boschelli, D.H.2    Ye, F.3    Golas, J.M.4    Boschelli, F.5
  • 37
    • 20144361879 scopus 로고    scopus 로고
    • Synthesis and Src kinase inhibitory activity of 2-phenyl and 2-thienyl-7-phenylaminothieno[3,2-b] pyridine-6-carbonitriles
    • Boschelli, D. H.; Wu, B.; Barrios Sosa, A. C.; Durutlic, H.; Chen, J. J.; Wang, Y.; Golas, J. M.; Lucas, J.; Boschelli, F. Synthesis and Src kinase inhibitory activity of 2-phenyl and 2-thienyl-7-phenylaminothieno[3,2-b] pyridine-6-carbonitriles. J. Med. Chem. 2005, 48, 3891-3902.
    • (2005) J. Med. Chem , vol.48 , pp. 3891-3902
    • Boschelli, D.H.1    Wu, B.2    Barrios Sosa, A.C.3    Durutlic, H.4    Chen, J.J.5    Wang, Y.6    Golas, J.M.7    Lucas, J.8    Boschelli, F.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.