메뉴 건너뛰기




Volumn 41, Issue 10, 1998, Pages 1631-1640

Syntheses and biological evaluation of indolocarbazoles, analogues of rebeccamycin, modified at the imide heterocycle

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; CARBAZOLE DERIVATIVE; DNA TOPOISOMERASE; HETEROCYCLIC AMINE; IMIDE; REBECCAMYCIN;

EID: 15144351325     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970843+     Document Type: Article
Times cited : (67)

References (33)
  • 1
    • 0030014783 scopus 로고    scopus 로고
    • DNA topoisomerases
    • Wang, J. C. DNA topoisomerases. Annu. Rev. Biochem. 1996, 65, 635-691.
    • (1996) Annu. Rev. Biochem. , vol.65 , pp. 635-691
    • Wang, J.C.1
  • 2
    • 0029552468 scopus 로고
    • Molecular, cellular, and clinical aspects of the pharmacology of 20(S) camptothecin and its derivatives
    • Rivory, L. P.; Robert, J. Molecular, cellular, and clinical aspects of the pharmacology of 20(S) camptothecin and its derivatives. Pharmacol. Ther. 1995, 68, 269-296.
    • (1995) Pharmacol. Ther. , vol.68 , pp. 269-296
    • Rivory, L.P.1    Robert, J.2
  • 5
    • 0028905348 scopus 로고
    • Novel indolocarbazole compound 6-N-formylamino-12,13-dihydro-1,11-dihydroxy-13-(βD-glucopyranosyl)-5H- indolo[2,3-a]pyrrolo-[3,4-c]carbazole-5,7(6H)-dione (NB-506): Its potent antitumor activities in mice
    • Arakawa, H.; Iguchi, T.; Monta, M.; Yoshinari, T.; Kojiri, K.; Suda, H.; Okura, A.; Nishimura, S. Novel indolocarbazole compound 6-N-formylamino-12,13-dihydro-1,11-dihydroxy-13-(βD-glucopyranosyl)-5H- indolo[2,3-a]pyrrolo-[3,4-c]carbazole-5,7(6H)-dione (NB-506): its potent antitumor activities in mice. Cancer Res. 1995, 55, 1316-1320.
    • (1995) Cancer Res. , vol.55 , pp. 1316-1320
    • Arakawa, H.1    Iguchi, T.2    Monta, M.3    Yoshinari, T.4    Kojiri, K.5    Suda, H.6    Okura, A.7    Nishimura, S.8
  • 6
    • 0023178261 scopus 로고
    • Production and biological activity of rebeccamycin, a novel antitumor agent
    • Bush, J. A.; Long, B. H.; Catino, J. J.; Bradner, W. T.; Tomita, K. Production and biological activity of rebeccamycin, a novel antitumor agent. J. Antibiot. 1987, 40, 668-678.
    • (1987) J. Antibiot. , vol.40 , pp. 668-678
    • Bush, J.A.1    Long, B.H.2    Catino, J.J.3    Bradner, W.T.4    Tomita, K.5
  • 8
    • 0023552288 scopus 로고
    • UCN-01, a selective inhibitor of protein kinase C from Streptomyces
    • Takahashi, I.; Kobayashi, E.; Asano, K.; Yoshida, M.; Nakano, H. UCN-01, a selective inhibitor of protein kinase C from Streptomyces. J. Antibiot. 1987, 40, 1782-1884.
    • (1987) J. Antibiot. , vol.40 , pp. 1782-1884
    • Takahashi, I.1    Kobayashi, E.2    Asano, K.3    Yoshida, M.4    Nakano, H.5
  • 9
    • 0000714445 scopus 로고    scopus 로고
    • Structure-activity relationships in a series of substituted indolocarbazoles: Topoisomerase I and protein kinase C inhibition and antitumoral and antimicrobial properties
    • Rodrigues-Pereira, E.; Belin, L.; Sancelme, M.; Prudhomme, M.; Ollier, M.; Rapp, M.; Sevère, D.; Riou, J. F.; Fabbro, D.; Meyer, T. Structure-activity relationships in a series of substituted indolocarbazoles: topoisomerase I and protein kinase C inhibition and antitumoral and antimicrobial properties. J. Med. Chem. 1996, 39, 4471-4477.
    • (1996) J. Med. Chem. , vol.39 , pp. 4471-4477
    • Rodrigues-Pereira, E.1    Belin, L.2    Sancelme, M.3    Prudhomme, M.4    Ollier, M.5    Rapp, M.6    Sevère, D.7    Riou, J.F.8    Fabbro, D.9    Meyer, T.10
  • 10
    • 0030944043 scopus 로고    scopus 로고
    • Sequence-selective DNA cleavage by mammalian topoisomerase I induced by DNA-intercalating indolocarbazole analogues of rebeccamycin
    • Bailly, C.; Riou, J. F.; Colson, P.; Houssier, C.; Rodrigues-Pereira, E.; Prudhomme, M. Sequence-selective DNA cleavage by mammalian topoisomerase I induced by DNA-intercalating indolocarbazole analogues of rebeccamycin. Biochemistry 1997, 36, 3917-3929.
    • (1997) Biochemistry , vol.36 , pp. 3917-3929
    • Bailly, C.1    Riou, J.F.2    Colson, P.3    Houssier, C.4    Rodrigues-Pereira, E.5    Prudhomme, M.6
  • 11
    • 0031938920 scopus 로고    scopus 로고
    • Recognition of specific sequences in DNA by a topoisomerase I inhibitor derived from the antitumor drug rebeccamycin
    • Bailly, C.; Colson, P.; Houssier, C.; Rodrigues Pereira, E.; Prudhomme, M.; Waring, M. J. Recognition of specific sequences in DNA by a topoisomerase I inhibitor derived from the antitumor drug rebeccamycin. Mol. Pharmacol. 1998, 53, 77-87.
    • (1998) Mol. Pharmacol. , vol.53 , pp. 77-87
    • Bailly, C.1    Colson, P.2    Houssier, C.3    Rodrigues Pereira, E.4    Prudhomme, M.5    Waring, M.J.6
  • 12
    • 0021816422 scopus 로고
    • Isolation and structure of rebeccamycin: A new antitumor antibiotic from Nocardia aerocolonigenes
    • Nettleton, D. E.; Doyle, T. W.; Krishnan, B.; Matsumoto, G. K.; Clardy, J. Isolation and structure of rebeccamycin: a new antitumor antibiotic from Nocardia aerocolonigenes. Tetrahedron Lett. 1985, 26, 4011-4014.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4011-4014
    • Nettleton, D.E.1    Doyle, T.W.2    Krishnan, B.3    Matsumoto, G.K.4    Clardy, J.5
  • 13
    • 9844260513 scopus 로고    scopus 로고
    • Syntheses and biological activities (topoisomerases inhibition, antitumoral and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moities and substituted on the imide nitrogen with a methyl group
    • Anizon, F.; Belin, L.; Moreau, P.; Sancelme, M.; Voldoire, A.; Prudhomme, M.; Oilier, M.; Severe, D.; Riou, J. F.; Bailly, C.; Fabbro, D.; Meyer, T. Syntheses and biological activities (topoisomerases inhibition, antitumoral and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moities and substituted on the imide nitrogen with a methyl group. J. Med. Chem. 1997, 40, 3456-3465.
    • (1997) J. Med. Chem. , vol.40 , pp. 3456-3465
    • Anizon, F.1    Belin, L.2    Moreau, P.3    Sancelme, M.4    Voldoire, A.5    Prudhomme, M.6    Oilier, M.7    Severe, D.8    Riou, J.F.9    Bailly, C.10    Fabbro, D.11    Meyer, T.12
  • 14
    • 0029046973 scopus 로고
    • Human immunodeficiency virus type 1 reverse transcriptase: Enhancement of activity by interaction with cellular topoisomerase 1
    • Takahashi, H.; Matsuda, M.; Kojima, A.; Sata, T.; Andoh, T.; Kuruta, T.; Nagashima, K.; Hall, W. W. Human immunodeficiency virus type 1 reverse transcriptase: enhancement of activity by interaction with cellular topoisomerase 1. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 5694-5698.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 5694-5698
    • Takahashi, H.1    Matsuda, M.2    Kojima, A.3    Sata, T.4    Andoh, T.5    Kuruta, T.6    Nagashima, K.7    Hall, W.W.8
  • 15
    • 0028567795 scopus 로고
    • DNA topoisomerases I & II cleavage sites in the type I human immunodeficiency virus (HIV-1) DNA promoter region
    • Pommier, Y.; Poddevin, B.; Gupta, M.; Jenkins, J. DNA topoisomerases I & II cleavage sites in the type I human immunodeficiency virus (HIV-1) DNA promoter region. Biochem. Biophys. Res. Commun. 1994, 205, 1601-1609.
    • (1994) Biochem. Biophys. Res. Commun. , vol.205 , pp. 1601-1609
    • Pommier, Y.1    Poddevin, B.2    Gupta, M.3    Jenkins, J.4
  • 16
    • 1542438495 scopus 로고
    • Reduction d'azides en amines par le formiate d'ammonium par "transfert d'hydrogène catalysé" (CTH)
    • Gartiser, T.; Selve, C.; Delpuech, J. J. Reduction d'azides en amines par le formiate d'ammonium par "transfert d'hydrogène catalysé" (CTH). Tetrahedron Lett. 1983, 24, 1609-1610.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1609-1610
    • Gartiser, T.1    Selve, C.2    Delpuech, J.J.3
  • 17
    • 0028373112 scopus 로고    scopus 로고
    • Indolocarbazole protein kinase C inhibitors from rebeccamycin
    • Fabre, S.; Prudhomme, M.; Sancelme, M.; Rapp, M. Indolocarbazole protein kinase C inhibitors from rebeccamycin. BioMed. Chem. 1994, 2, 73-77; 1997, 5, 2109.
    • (1994) BioMed. Chem. , vol.2 , pp. 73-77
    • Fabre, S.1    Prudhomme, M.2    Sancelme, M.3    Rapp, M.4
  • 18
    • 0028373112 scopus 로고    scopus 로고
    • Fabre, S.; Prudhomme, M.; Sancelme, M.; Rapp, M. Indolocarbazole protein kinase C inhibitors from rebeccamycin. BioMed. Chem. 1994, 2, 73-77; 1997, 5, 2109.
    • (1997) BioMed. Chem. , vol.5 , pp. 2109
  • 20
    • 0030014794 scopus 로고    scopus 로고
    • Control of dissymetry in the synthesis of (+)-tjipanazole F2
    • Gilbert, E. J.; Van Vranken, D. L. Control of dissymetry in the synthesis of (+)-tjipanazole F2. J. Am. Chem. Soc. 1996, 118, 5500-5501.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5500-5501
    • Gilbert, E.J.1    Van Vranken, D.L.2
  • 21
    • 0029826028 scopus 로고    scopus 로고
    • Synthesis and anti-platelet aggregation activity of water-soluble staurosporine derivatives
    • Yamada, R.; Seto, M.; Sasaki, Y.; Sunazuka, T.; Harigaya, H.; Iwai, Y.; Omura, S. Synthesis and anti-platelet aggregation activity of water-soluble staurosporine derivatives. J. Antibiot. 1996, 49, 1070-1072.
    • (1996) J. Antibiot. , vol.49 , pp. 1070-1072
    • Yamada, R.1    Seto, M.2    Sasaki, Y.3    Sunazuka, T.4    Harigaya, H.5    Iwai, Y.6    Omura, S.7
  • 25
    • 0027336298 scopus 로고
    • Go 6976, a selective inhibitor of protein kinase C, is a potent antagonist of human immunodeficiency virus 1 induction from latent/low level-producing reservoir cells in vitro
    • Qatsha, K. A.; Rudolph, C.; Marmé, D.; Schächtele, C.; May, W. S. Go 6976, a selective inhibitor of protein kinase C, is a potent antagonist of human immunodeficiency virus 1 induction from latent/low level-producing reservoir cells in vitro. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 4674-4678.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 4674-4678
    • Qatsha, K.A.1    Rudolph, C.2    Marmé, D.3    Schächtele, C.4    May, W.S.5
  • 26
    • 0027403716 scopus 로고
    • Three inhibitors of type 1 human immunodeficiency virus long terminal repeat-directed gene expression and virus replication
    • Li, C. J.; Zhang, L. J.; Dezube, B. J.; Crumpacker, C. S.; Pardee, A. B. Three inhibitors of type 1 human immunodeficiency virus long terminal repeat-directed gene expression and virus replication. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1839-1842.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 1839-1842
    • Li, C.J.1    Zhang, L.J.2    Dezube, B.J.3    Crumpacker, C.S.4    Pardee, A.B.5
  • 27
    • 0026082794 scopus 로고
    • Inhibition of human immunodeficiency virus (HIV-1) replication by cytotoxic doses of camptothecin, a topoisomerase I inhibitor
    • Priel, E.; Showalter, S. D.; Blair, D. G. Inhibition of human immunodeficiency virus (HIV-1) replication by cytotoxic doses of camptothecin, a topoisomerase I inhibitor. AIDS Res. Hum. Retroviruses 1991, 7, 65-72.
    • (1991) AIDS Res. Hum. Retroviruses , vol.7 , pp. 65-72
    • Priel, E.1    Showalter, S.D.2    Blair, D.G.3
  • 28
    • 0025850677 scopus 로고
    • The topoisomerase I inhibitor, camptothecin, inhibits equine infectious anemia virus replication in chronically infected CF2Th cells
    • Priel, E.; Showalter, S. D.; Roberts, M.; Oroszlan, S.; Blair, D. G. The topoisomerase I inhibitor, camptothecin, inhibits equine infectious anemia virus replication in chronically infected CF2Th cells. J. Virol. 1991, 65, 4137-4141.
    • (1991) J. Virol. , vol.65 , pp. 4137-4141
    • Priel, E.1    Showalter, S.D.2    Roberts, M.3    Oroszlan, S.4    Blair, D.G.5
  • 29
    • 0027472338 scopus 로고
    • Sequential modifications of topoisomerase I activity in a camptothecin resistant cell line established by progressive adaptation
    • Madelaine, J.; Prost, S.; Naudin, A.; Riou, G.; Lavelle, F.; Riou, J. E. Sequential modifications of topoisomerase I activity in a camptothecin resistant cell line established by progressive adaptation. Biochem. Pharmacol. 1993, 45, 339-348.
    • (1993) Biochem. Pharmacol. , vol.45 , pp. 339-348
    • Madelaine, J.1    Prost, S.2    Naudin, A.3    Riou, G.4    Lavelle, F.5    Riou, J.E.6
  • 30
    • 0028899328 scopus 로고
    • Comparison of different footprinting methodologies for detecting binding sites for a small ligand on DNA
    • Bailly, C.; Waring, M. J. Comparison of different footprinting methodologies for detecting binding sites for a small ligand on DNA. J. Biomol. Struct. Dyn. 1995, 12, 869-898.
    • (1995) J. Biomol. Struct. Dyn. , vol.12 , pp. 869-898
    • Bailly, C.1    Waring, M.J.2
  • 31
    • 0028124660 scopus 로고
    • Bicyclic imidazo derivatives, a new class of highly selective inhibitors for the human immunodeficiency virus type 1
    • Moog, C.; Wick, A.; Le Ber, P.; Kirn, A.; Aubertin, A. M. Bicyclic imidazo derivatives, a new class of highly selective inhibitors for the human immunodeficiency virus type 1. Antiviral Res. 1994, 24, 275-288.
    • (1994) Antiviral Res. , vol.24 , pp. 275-288
    • Moog, C.1    Wick, A.2    Le Ber, P.3    Kirn, A.4    Aubertin, A.M.5
  • 32
    • 0002607770 scopus 로고
    • Dose-effect analysis with microcomputers: Quantitation of ED50 LD50, synergism, antagonism, lowdose risk, receptor binding and enzyme kinetics
    • Elsevier-Biosoft, Elsevier Science Publishers: Cambridge, U.K.
    • Chou, J.; Chou, T. C. Dose-effect analysis with microcomputers: quantitation of ED50 LD50, synergism, antagonism, lowdose risk, receptor binding and enzyme kinetics. Computer software for Apple II series and IBM-PC and instruction manual; Elsevier-Biosoft, Elsevier Science Publishers: Cambridge, U.K., 1985; pp 19-28.
    • (1985) Computer Software for Apple II Series and IBM-PC and Instruction Manual , pp. 19-28
    • Chou, J.1    Chou, T.C.2
  • 33
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxic assays
    • Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxic assays. J. Immunol. Methods 1983, 65, 55-63.
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.