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Volumn 54, Issue , 2012, Pages 626-636

Synthesis and biological evaluation of analogs of the marine alkaloids granulatimide and isogranulatimide

Author keywords

G2 M checkpoint inhibitors; Granulatimide; Isogranulatimide; Marine alkaloid; Protein kinases; Pyrazolic analogs; Pyrrolic analogs; Quantitative videomicroscopy

Indexed keywords

11H 1,5,11,11B TETRAAZABENZO[A]TRINDENE 4,6 DIONE; 3H PYRAZOLO[4,3 A]PYRROLO[3,4 C]CARBAZOLE 4,6(5H,11H) DIONE; 5 (3 FLUOROPHENYL) N (3 PIPERIDINYL) 3 UREIDO 2 THIOPHENECARBOXAMIDE; 8 HYDROXY 11H 1,5,11,11B TETRAAZABENZO[A]TRINDENE 4,6 DIONE; 8 METHOXY 11H 1,5,11,11B TETRAAZABENZO[A]TRINDENE 4,6 DIONE; 8 METHOXY 3H PYRAZOLO[4,3 A]PYRROLO[3,4 C]CARBAZOLE 4,6(5H,11H) DIONE; 8 METHYL 11H 1,5,11,11B TETRAAZABENZO[A]TRINDENE 4,6 DIONE; 8 METHYL 11H 3A,5,11 TRIAZABENZO[A]TRINDENE 4,6 DIONE; 8 METHYL 3H PYRAZOLO[4,3 A]PYRROLO[3,4 C]CARBAZOLE 4,6(5H,11H) DIONE; ACETAMIDE DERIVATIVE; ALKALOID; CYTOSTATIC AGENT; DIBROMOMALEIMIDE; GLYOXYLIC ACID DERIVATIVE; GRANULATIMIDE; GRANULATIMIDE DERIVATIVE; INDOLE DERIVATIVE; ISOGRANULATIMIDE; ISOGRANULATIMIDE DERIVATIVE; MALEIMIDE; MALEIMIDE DERIVATIVE; PROTEIN SERINE THREONINE KINASE; PYRAZOLE; PYRROLE; UNCLASSIFIED DRUG;

EID: 84864399435     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.012     Document Type: Article
Times cited : (25)

References (34)
  • 1
    • 0038052805 scopus 로고    scopus 로고
    • The cell cycle: A review of regulation, deregulation and therapeutic targets in cancer
    • DOI 10.1046/j.1365-2184.2003.00266.x
    • K. Vermeulen, D.R. Van Bockstaele, and Z.N. Berneman The cell cycle: a review of regulation, deregulation and therapeutic target in cancer Cell Prolif. 36 2003 131 149 (Pubitemid 36808270)
    • (2003) Cell Proliferation , vol.36 , Issue.3 , pp. 131-149
    • Vermeulen, K.1    Van Bockstaele, D.R.2    Berneman, Z.N.3
  • 4
    • 0032567379 scopus 로고    scopus 로고
    • Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum: Structure elucidation and synthesis
    • DOI 10.1021/jo981607p
    • R.G.S. Berlinck, R. Britton, E. Piers, L. Lim, M. Roberge, R. Moreira da Rocha, and R. Andersen Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the brazilian ascidian Didemnum granulatum: structure elucidation and synthesis J. Org. Chem. 63 1998 9850 9856 (Pubitemid 29035142)
    • (1998) Journal of Organic Chemistry , vol.63 , Issue.26 , pp. 9850-9856
    • Berlmck, R.G.S.1    Britton, R.2    Piers, E.3    Lim, L.4    Roberge, M.5    Rosana Moreira Da Rocha6    Andersen, R.J.7
  • 8
    • 34250865564 scopus 로고    scopus 로고
    • CDC25 phosphatases in cancer cells: Key players? Good targets?
    • DOI 10.1038/nrc2169, PII NRC2169
    • R. Boutros, V. Lobjois, and B. Ducommun CDC25 phosphatases in cancer cells: key players? Good targets? Nat. Rev. Cancer 7 2007 495 507 (Pubitemid 46985396)
    • (2007) Nature Reviews Cancer , vol.7 , Issue.7 , pp. 495-507
    • Boutros, R.1    Lobjois, V.2    Ducommun, B.3
  • 10
    • 75149126421 scopus 로고    scopus 로고
    • Marine pyrrolocarbazoles and analogues: Synthesis and kinase inhibition
    • S. Deslandes, S. Chassaing, and E. Delfourne Marine pyrrolocarbazoles and analogues: synthesis and kinase inhibition Mar. Drugs 7 2009 754 786
    • (2009) Mar. Drugs , vol.7 , pp. 754-786
    • Deslandes, S.1    Chassaing, S.2    Delfourne, E.3
  • 11
    • 0242417482 scopus 로고    scopus 로고
    • Synthesis of isogranulatimide analogues possessing a pyrrole moiety instead of an imidazole heterocycle
    • DOI 10.1016/S0040-4039(03)00837-2
    • B. Hugon, B. Pfeiffer, P. Renard, and M. Prudhomme Synthesis of isogranulatimide analogues possessing a pyrrole moiety instead of an imidazole heterocycle Tetrahedron Lett. 44 2003 3927 3930 (Pubitemid 36513806)
    • (2003) Tetrahedron Letters , vol.44 , Issue.20 , pp. 3927-3930
    • Hugon, B.1    Pfeiffer, B.2    Renard, P.3    Prudhomme, M.4
  • 12
    • 84989492823 scopus 로고
    • High yield selective bromination and iodination of indoles in N, N-dimethylformamide
    • V. Bocchi, and G. Palla High yield selective bromination and iodination of indoles in N, N-dimethylformamide Synthesis 1982 1096 1097
    • (1982) Synthesis , pp. 1096-1097
    • Bocchi, V.1    Palla, G.2
  • 15
    • 0001186193 scopus 로고    scopus 로고
    • A new efficient method for the synthesis of bisindolylmaleimides
    • M.M. Faul, L.L. Winneroski, and C.A. Krumrich A new efficient method for the synthesis of bisindolylmaleimides J. Org. Chem. 63 1998 6053 6058
    • (1998) J. Org. Chem. , vol.63 , pp. 6053-6058
    • Faul, M.M.1    Winneroski, L.L.2    Krumrich, C.A.3
  • 16
    • 0034723302 scopus 로고    scopus 로고
    • Improved synthesis of isogranulatimide, a G2 checkpoint inhibitor. Syntheses of didemnimide C, isodidemnimide A, neodidemnimide A, 17- methylgranulatimide, and isogranulatimides A-C
    • DOI 10.1021/jo9914723
    • E. Piers, R. Britton, and R.J. Andersen Improved synthesis of isogranulatimide, a G2 checkpoint inhibitor. Synthesis of didemnimide C, isodidemnimide A, neodidemnimide A, 17-methylgranulatimide and isogranulatimide A-C J. Org. Chem. 65 2000 530 535 (Pubitemid 30061139)
    • (2000) Journal of Organic Chemistry , vol.65 , Issue.2 , pp. 530-535
    • Piers, E.1    Britton, R.2    Andersen, R.J.3
  • 17
    • 0000220487 scopus 로고
    • New methods of synthesis of β-aminoethylpyrazoles
    • R.G. Jones, and M.J. Mann New methods of synthesis of β-aminoethylpyrazoles J. Am. Chem. Soc. 71 1953 4048 4052
    • (1953) J. Am. Chem. Soc. , vol.71 , pp. 4048-4052
    • Jones, R.G.1    Mann, M.J.2
  • 19
    • 34948883332 scopus 로고    scopus 로고
    • The amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts
    • DOI 10.1593/neo.07535
    • P. Dumont, L. Ingrassia, S. Rouzeau, F. Ribaucour, S. Thomas, I. Roland, F. Darro, F. Lefranc, and R. Kiss The Amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts Neoplasia 9 2007 766 776 (Pubitemid 47523238)
    • (2007) Neoplasia , vol.9 , Issue.9 , pp. 766-776
    • Dumont, P.1    Ingrassia, L.2    Rouzeau, S.3    Ribaucour, F.4    Thomas, S.5    Roland, I.6    Darro, F.7    Lefranc, F.8    Kiss, R.9
  • 20
    • 0036682304 scopus 로고    scopus 로고
    • Evaluation of the efficiency of chemotherapy in in vivo orthotopic models of human glioma cells with and without 1p19q deletions and in C6 rat orthotopic allografts serving for the evaluation of surgery combined with chemotherapy
    • DOI 10.1002/cncr.10710
    • F. Branle, F. Lefranc, I. Camby, J. Jeuken, A. Geurts-Moespot, S. Sprenger, F. Sweep, R. Kiss, and I. Salmon Evaluation of the efficiency of chemotherapy in in vivo orthotopic models of human glioma cells with and without 1p19q deletions and in C6 rat orthotopic allografts serving for the evaluation of surgery combined with chemotherapy Cancer 95 2002 641 655 (Pubitemid 34810191)
    • (2002) Cancer , vol.95 , Issue.3 , pp. 641-655
    • Branle, F.1    Lefranc, F.2    Camby, I.3    Jeuken, J.4    Geurts-Moespot, A.5    Sprenger, S.6    Sweep, F.7    Kiss, R.8    Salmon, I.9
  • 23
    • 33744824903 scopus 로고    scopus 로고
    • Cardenolide-induced lysosomal membrane permeabilization demonstrates therapeutic benefits in experimental human non-small cell lung cancers
    • DOI 10.1593/neo.05850
    • T. Mijatovic, V. Mathieu, J.F. Gaussin, N. De Neve, F. Ribaucour, E. Van Quaquebeke, P. Dumont, F. Darro, and R. Kiss Cardenolide-induced lysosomal membrane permeabilization demonstrates therapeutic benefits in experimental human non-small cell lung cancers Neoplasia 8 2006 402 412 (Pubitemid 43830747)
    • (2006) Neoplasia , vol.8 , Issue.5 , pp. 402-412
    • Mijatovic, T.1    Mathieu, V.2    Gaussin, J.-F.3    De Neve, N.4    Ribaucour, F.5    Van Quaquebeke, E.6    Dumont, P.7    Darro, F.8    Kiss, R.9
  • 25
    • 84872429604 scopus 로고    scopus 로고
    • http://www.sanger.ac.uk/perl/genetics/CGP/core-line-viewer?action= cell-lines.
  • 28
    • 45549097605 scopus 로고    scopus 로고
    • G2/M checkpoint stringency is a key parameter in the sensitivity of AML cells to genotoxic stress
    • DOI 10.1038/sj.onc.1211041, PII 1211041
    • C. Didier, M. Quaranta, C. Cavelier, M.-O. Galcera, C. Demur, G. Laurent, S. Manenti, and B. Ducommun G2/M checkpoint stringency is a key parameter in the sensitivity of AML cells to genotoxic stress Oncogene 27 2008 3811 3820 (Pubitemid 351862053)
    • (2008) Oncogene , vol.27 , Issue.27 , pp. 3811-3820
    • Didier, C.1    Cavelier, C.2    Quaranta, M.3    Galcera, M.-O.4    Demur, C.5    Laurent, G.6    Manenti, S.7    Ducommun, B.8
  • 30
    • 33847161244 scopus 로고    scopus 로고
    • Can anti-migratory drugs be screened in vitro? A review of 2D and 3D assays for the quantitative analysis of cell migration
    • DOI 10.1002/med.20078
    • C. Decaestecker, O. Debeir, P. Van Ham, and R. Kiss Can anti-migratory drugs be screened in vitro? A review of 2D and 3D assays for the quantitative analysis of cell migration Med. Res. Rev. 27 2007 149 176 (Pubitemid 46281145)
    • (2007) Medicinal Research Reviews , vol.27 , Issue.2 , pp. 149-176
    • Decaestecker, C.1    Debeir, O.2    Van Ham, P.3    Kiss, R.4
  • 31
    • 1242351268 scopus 로고    scopus 로고
    • Extracellular S100A4 stimulates the migration rate of astrocytic tumor cells by modifying the organization of their actin cytoskeleton
    • DOI 10.1016/S1570-9639(02)00447-8, PII S1570963902004478
    • N. Belot, R. Pochet, C.W. Heizmann, R. Kiss, and C. Decaestecker Extracellular S100A4 stimulates the migration rate of astrocytic tumor cells by modifying the organization of their actin cytoskeleton Biochim. Biophys. Acta 1600 2002 74 83 (Pubitemid 38224401)
    • (2002) Biochimica et Biophysica Acta - Proteins and Proteomics , vol.1600 , Issue.1-2 , pp. 74-83
    • Belot, N.1    Pochet, R.2    Heizmann, C.W.3    Kiss, R.4    Decaestecker, C.5
  • 32
    • 0035808457 scopus 로고    scopus 로고
    • Indirubins inhibit glycogen synthase kinase-3β and CDK5/P25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease. A property common to most cyclin-dependent kinase inhibitors?
    • DOI 10.1074/jbc.M002466200
    • S. Leclerc, M. Garnier, R. Hoessel, D. Marko, J.A. Bibb, G.L. Snyder, P. Greengard, J. Biernat, E.-M. Mandelkow, G. Eisenbrand, and L. Meijer Indirubins inhibit glycogen synthase kinase-3β and CDK5/P25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease: a property common to most cyclin-dependent kinase inhibitors ? J. Biol. Chem. 276 2001 251 260 (Pubitemid 32050314)
    • (2001) Journal of Biological Chemistry , vol.276 , Issue.1 , pp. 251-260
    • Leclerc, S.1    Garnier, M.2    Hoessel, R.3    Marko, D.4    Bibb, J.A.5    Snyder, G.L.6    Greengard, P.7    Biernat, J.8    Wu, Y.-Z.9    Mandelkow, E.-M.10    Eisenbrand, G.11    Meijert, L.12
  • 34
    • 34247335032 scopus 로고    scopus 로고
    • Purification of CK1 by affinity chromatography on immobilised axin
    • DOI 10.1016/j.pep.2007.02.020, PII S1046592807000642
    • J. Reinhardt, Y. Ferandin, and L. Meijer Purification of CK1 by affinity chromatography on immobilised axin Protein Expr. Purif 54 2007 101 109 (Pubitemid 46636329)
    • (2007) Protein Expression and Purification , vol.54 , Issue.1 , pp. 101-109
    • Reinhardt, J.1    Ferandin, Y.2    Meijer, L.3


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