메뉴 건너뛰기




Volumn 51, Issue 5, 2008, Pages 1252-1259

Structure-based optimization of pyrazolo[3,4-d]pyrimidines as Abl inhibitors and antiproliferative agents toward human leukemia cell lines

Author keywords

[No Author keywords available]

Indexed keywords

2 [2 METHOXY 5 (2,4,6 TRIMETHOXYSTYRYLSULFONYLMETHYL)ANILINO]PROPIONIC ACID; 4 (3 DIMETHYLAMINO 1 PYRROLIDINYLMETHYL) 3 TRIFLUOROMETHYL N [4 METHYL 3 [[4 (5 PYRIMIDINYL) 2 PYRIMIDINYL]AMINO]PHENYL]BENZAMIDE; 4 AMINO 7 TERT BUTYL 5 (4 CHLOROPHENYL)PYRAZOLO[3,4 D]PYRIMIDINE; ABELSON KINASE; AP 23846; CYCLOPROPANECARBOXYLIC ACID [4 [4 (4 METHYL 1 PIPERAZINYL) 6 (5 METHYL 2H PYRAZOL 3 YLAMINO) 2 PYRIMIDINYLTHIO]PHENYL]AMIDE; DASATINIB; ENZYME INHIBITOR; HALIDE; IMATINIB; NILOTINIB; UNCLASSIFIED DRUG;

EID: 41649083169     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701240c     Document Type: Article
Times cited : (87)

References (29)
  • 1
    • 41649095101 scopus 로고    scopus 로고
    • Nowell, P. C.; Hungerford, D. A. A minute chromosome in chronic granulocytic leukemia. Science 1960, 132, 1497-1501.
    • Nowell, P. C.; Hungerford, D. A. A minute chromosome in chronic granulocytic leukemia. Science 1960, 132, 1497-1501.
  • 2
    • 0015694748 scopus 로고    scopus 로고
    • Rowley, J. D. Letter: a new consistent chromosomal abnormality in chronic myelogenous leukemia identified by quinacrine fluorescence and Giemsa staining. Nature 1973, 243, 290-293.
    • Rowley, J. D. Letter: a new consistent chromosomal abnormality in chronic myelogenous leukemia identified by quinacrine fluorescence and Giemsa staining. Nature 1973, 243, 290-293.
  • 3
    • 0033614446 scopus 로고    scopus 로고
    • Chronic myeloid leukemia
    • Sawyers, C. L. Chronic myeloid leukemia. N. Engl. J. Med. 1999, 340, 1330-1340.
    • (1999) N. Engl. J. Med , vol.340 , pp. 1330-1340
    • Sawyers, C.L.1
  • 4
    • 0025348013 scopus 로고
    • Tyrosine kinase activity and transformation potency of Bcr-Abl oncogene products
    • Lugo, T. G.; Pendergast, A. M.; Muller, A. J.; Witte, O. N. Tyrosine kinase activity and transformation potency of Bcr-Abl oncogene products. Science 1990, 247, 1079-1082.
    • (1990) Science , vol.247 , pp. 1079-1082
    • Lugo, T.G.1    Pendergast, A.M.2    Muller, A.J.3    Witte, O.N.4
  • 5
    • 0037153476 scopus 로고    scopus 로고
    • Selective pyrrolo-pyrimidine inhibitors reveal a necessary role for Src family kinases in Bcr-Abl signal transduction and oncogenesis
    • Wilson, M. B.; Schreiner, S. J.; Choi, H. J.; Kamens, J.; Smithgall, T. E. Selective pyrrolo-pyrimidine inhibitors reveal a necessary role for Src family kinases in Bcr-Abl signal transduction and oncogenesis. Oncogene 2002, 21, 8075-8088.
    • (2002) Oncogene , vol.21 , pp. 8075-8088
    • Wilson, M.B.1    Schreiner, S.J.2    Choi, H.J.3    Kamens, J.4    Smithgall, T.E.5
  • 8
    • 0035800507 scopus 로고    scopus 로고
    • Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amlification
    • Gorre, M. E.; Mohammed, M.; Ellwood, K.; Hsu, N.; Paquette, R.; Rao, P. N.; Sawyers, C. L. Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amlification. Science 2001, 293, 876-880.
    • (2001) Science , vol.293 , pp. 876-880
    • Gorre, M.E.1    Mohammed, M.2    Ellwood, K.3    Hsu, N.4    Paquette, R.5    Rao, P.N.6    Sawyers, C.L.7
  • 9
    • 31344472945 scopus 로고    scopus 로고
    • Novel targeted therapies to overcome imatinib mesylate resistance in chronic myeloid leukemia (CML)
    • Walz, C.; Sattler, M. Novel targeted therapies to overcome imatinib mesylate resistance in chronic myeloid leukemia (CML). Crit. Rev. Oncol. Hematol. 2006, 57, 145-164.
    • (2006) Crit. Rev. Oncol. Hematol , vol.57 , pp. 145-164
    • Walz, C.1    Sattler, M.2
  • 12
    • 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
  • 13
    • 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
  • 14
    • 36949004277 scopus 로고    scopus 로고
    • Synthetic Src-kinase domain inhibitors and their structural requirements
    • Schenone, S.; Manetti, F.; Botta, M. Synthetic Src-kinase domain inhibitors and their structural requirements. Anti-Cancer Agents Med. Chem. 2007, 7, 660-680.
    • (2007) Anti-Cancer Agents Med. Chem , vol.7 , pp. 660-680
    • Schenone, S.1    Manetti, F.2    Botta, M.3
  • 15
    • 19944428353 scopus 로고    scopus 로고
    • Lombardo, L. J.; Lee, F. Y.; Chen, P.; Norris, D.; Barrish, J. C.; Behnia, K.; Castaneda, S.; Cornelius, L. A.; Das, J.; Doweyko, A. M.; Fairchild, C.; Hunt, J. T.; Inigo, J.; Johnston, K.; Kamath, A.; Kan, D.; Klei, H.; Marathe, P.; Pang, S.; Peterson, R.; Pitt, S.; Schieven, G. L.; Schimdt, R. J.; Tokarski, J.; Wen, M. L.; Wityak, J.; Borzilleri, R. M. Discovery of N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-l-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.
    • (a) Lombardo, L. J.; Lee, F. Y.; Chen, P.; Norris, D.; Barrish, J. C.; Behnia, K.; Castaneda, S.; Cornelius, L. A.; Das, J.; Doweyko, A. M.; Fairchild, C.; Hunt, J. T.; Inigo, J.; Johnston, K.; Kamath, A.; Kan, D.; Klei, H.; Marathe, P.; Pang, S.; Peterson, R.; Pitt, S.; Schieven, G. L.; Schimdt, R. J.; Tokarski, J.; Wen, M. L.; Wityak, J.; Borzilleri, R. M. Discovery of N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-l-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.
  • 16
    • 33750989362 scopus 로고    scopus 로고
    • Das, J.; Chen, P.; Norris, D.; Padmanabha, R.; Lin, J.; Moquin, R. V.; Shen, Z.; Cook, L. S.; Doweyko, A. M.; Pitt, S.; Pang, S.; Shen, D. R.; Fang, Q.; de Fex, H. F.; McIntyre, K. W.; Shuster, D. J.; Gillooly, K. M.; Behnia, K.; Schieven, G. L.; Wityak, J.; Barrish, J. C. 2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-l- piperazinyl)]-2methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J. Med. Chem. 2006, 49, 6819-6832.
    • (b) Das, J.; Chen, P.; Norris, D.; Padmanabha, R.; Lin, J.; Moquin, R. V.; Shen, Z.; Cook, L. S.; Doweyko, A. M.; Pitt, S.; Pang, S.; Shen, D. R.; Fang, Q.; de Fex, H. F.; McIntyre, K. W.; Shuster, D. J.; Gillooly, K. M.; Behnia, K.; Schieven, G. L.; Wityak, J.; Barrish, J. C. 2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-l- piperazinyl)]-2methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J. Med. Chem. 2006, 49, 6819-6832.
  • 19
    • 41649098078 scopus 로고    scopus 로고
    • accessed 2006
    • U.S. Food and Drug Administration, http://www.fda.gov/bbs/topics/NEWS/ 2006/NEW01400.html (accessed 2006).
  • 22
    • 33748094100 scopus 로고    scopus 로고
    • In vivo antiproliferative effect of NS-187, a dual Bcr-Abl/Lyn tyrosine kinase inhibitor, on leukemic cells harbouring Abl kinase domain mutations
    • Naito, H.; Kimura, S.; Nakaya, Y.; Naruoka, H.; Kimura, S.; Ito, S.; Wakayama, T.; Maekawa, T.; Hirabayashi, K. In vivo antiproliferative effect of NS-187, a dual Bcr-Abl/Lyn tyrosine kinase inhibitor, on leukemic cells harbouring Abl kinase domain mutations. Leuk. Res. 2006, 11, 1443-1446.
    • (2006) Leuk. Res , vol.11 , pp. 1443-1446
    • Naito, H.1    Kimura, S.2    Nakaya, Y.3    Naruoka, H.4    Kimura, S.5    Ito, S.6    Wakayama, T.7    Maekawa, T.8    Hirabayashi, K.9
  • 23
    • 34247615972 scopus 로고    scopus 로고
    • Structural basis for potent inhibition of the Aurora kinases and a T315I multidrug resistant mutant form of Abl kinase by VX-680
    • Cheetham, G. M.; Charlton, P. A.; Golec, J. M.; Pollard, J. R. Structural basis for potent inhibition of the Aurora kinases and a T315I multidrug resistant mutant form of Abl kinase by VX-680. Cancer Lett. 2007, 251, 323-329.
    • (2007) Cancer Lett , vol.251 , pp. 323-329
    • Cheetham, G.M.1    Charlton, P.A.2    Golec, J.M.3    Pollard, J.R.4
  • 25
    • 41649104211 scopus 로고    scopus 로고
    • Grid 22; Molecular Discovery Ltd: Pinner, Middlesex, U.K.
    • Grid 22; Molecular Discovery Ltd: Pinner, Middlesex, U.K.
  • 26
    • 0033800498 scopus 로고    scopus 로고
    • Cruciani, G.; Pastor, M.; Guba, W. Volsurf: a new tool for the pharmacokinetic optimization of lead compounds. Eur. J. Pharm. Sci. 2000, 11 (2), S29-S39.
    • (a) Cruciani, G.; Pastor, M.; Guba, W. Volsurf: a new tool for the pharmacokinetic optimization of lead compounds. Eur. J. Pharm. Sci. 2000, 11 (2), S29-S39.
  • 27
    • 84907806183 scopus 로고    scopus 로고
    • at the Volsurf web site
    • (b) Further information at the Volsurf web site: http://www.moldiscovery. com/docs/volsurf.
    • Further information


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.