메뉴 건너뛰기




Volumn 48, Issue 7, 2005, Pages 2600-2611

Syntheses and biological activities of rebeccamycin analogues with uncommon sugars

Author keywords

[No Author keywords available]

Indexed keywords

11,12 DIHYDRO 11 (3 AMINO 2,3,6 TRIDEOXY BETA LEVO LYXOHEXOSYL)INDOLO[2,3 A]CARBAZOLE 5,6 DICARBOXYLIC ANHYDRIDE; 11,12 DIHYDRO 11 (3 BENZOXYAMIDO 2,3,6 TRIDEOXY BETA LEVO LYXOHEXOSYL)INDOLO[2,3 A]CARBAZOLE 5,6 DICARBOXYLIC ANHYDRIDE; 2,3,6 DEOXYGLUCOSE; 2,6 DEOXYGLUCOSE; 6 METHYL 12 (2 DEOXY ALPHA LEVO RHAMNOPYRANOSYL) 6,7,12,13 TETRAHYDROINDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 6 METHYL 12 (2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 6,7,12,13 TETRAHYDROINDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 6 METHYL 12 (2 DEOXY BETA LEVO RHAMNOPYRANOSYL) 6,7,12,13 TETRAHYDROINDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 6 METHYL 12 (3 BENZOXYAMIDO 2,3,6 TRIDEOXY BETA LEVO LYXOHEXOSYL) 6,7,12,13 TETRAHYDROINDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; AGLYCONE; AT 2433 A1; AT 2433 B1; CARBOHYDRATE; CYTOTOXIC AGENT; DAUNORUBICIN; DEOXYGLUCOSE; DNA TOPOISOMERASE; DNA TOPOISOMERASE INHIBITOR; GLYCOSIDE; IMIDE; INDOLE DERIVATIVE; INDOLECARBAZOLE DERIVATIVE; REBECCAMYCIN; REBECCAMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 20244380623     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0493764     Document Type: Article
Times cited : (66)

References (39)
  • 1
    • 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
  • 2
    • 0025788486 scopus 로고
    • A new antitumor substance, BE-13793C, produced by a streptomycete. Taxonomy, fermentation, isolation, structure determination and biological activity
    • Kojiri, K.; Kondo, H.; Yoshinari, T.; Arakawa, H.; Nakajima, S. et al. A new antitumor substance, BE-13793C, produced by a streptomycete. Taxonomy, fermentation, isolation, structure determination and biological activity. J. Antibiot. 1991, 44, 723-728.
    • (1991) J. Antibiot. , vol.44 , pp. 723-728
    • Kojiri, K.1    Kondo, H.2    Yoshinari, T.3    Arakawa, H.4    Nakajima, S.5
  • 3
    • 0021816422 scopus 로고
    • Isolation and structure of rebeccamycin - A new antitumor antibiotic from Nocardia aerocoligenes
    • Nettleton, D. E.; Doyle, T. W.; Krishnan, B.; Matsumoto, G. K.; Clardy, J. Isolation and structure of rebeccamycin - a new antitumor antibiotic from Nocardia aerocoligenes. 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
  • 5
    • 0029035461 scopus 로고
    • Antitumor activities of a new indolocarbazole substance, NB-506, and establishment of NB-506-resistant cell lines, SBC-3/NB
    • Kanzawa, F.; Nishio, K.; Kubota, N.; Saijo, N. Antitumor activities of a new indolocarbazole substance, NB-506, and establishment of NB-506-resistant cell lines, SBC-3/NB. Cancer Res. 1995, 55, 2806-2813.
    • (1995) Cancer Res. , vol.55 , pp. 2806-2813
    • Kanzawa, F.1    Nishio, K.2    Kubota, N.3    Saijo, N.4
  • 6
    • 0035300476 scopus 로고    scopus 로고
    • Identification of breast cancer resistant protein/mitoxantrone resistance/placenta-specific, ATP-binding cassette transporter as a transporter of NB-506 and J-107088, topoisomerase I inhibitors with an indolocarbazole structure
    • Komatani, H.; Kotani, H.; Hara, Y.; Nakagawa, R.; Matsumoto, M. et al. Identification of breast cancer resistant protein/mitoxantrone resistance/placenta-specific, ATP-binding cassette transporter as a transporter of NB-506 and J-107088, topoisomerase I inhibitors with an indolocarbazole structure. Cancer Res. 2001, 61, 2827-2832.
    • (2001) Cancer Res. , vol.61 , pp. 2827-2832
    • Komatani, H.1    Kotani, H.2    Hara, Y.3    Nakagawa, R.4    Matsumoto, M.5
  • 9
    • 9844260513 scopus 로고    scopus 로고
    • Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group
    • Anizon, F.; Belin, L.; Moreau, P.; Sancelme, M.; Voldoire, A. et al. Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties 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
  • 10
    • 15144351325 scopus 로고    scopus 로고
    • Syntheses and biological evaluation of indolocarbazoles, analogues of rebeccamycin, modified at the imide heterocycle
    • Moreau, P.; Anizon, F.; Sancelme, M.; Prudhomme, M.; Bailly, C. et al. Syntheses and biological evaluation of indolocarbazoles, analogues of rebeccamycin, modified at the imide heterocycle, J. Med. Chem. 1998, 41, 1631-1640.
    • (1998) J. Med. Chem. , vol.41 , pp. 1631-1640
    • Moreau, P.1    Anizon, F.2    Sancelme, M.3    Prudhomme, M.4    Bailly, C.5
  • 11
    • 0033199091 scopus 로고    scopus 로고
    • Mode of action of a new indolocarbazole anticancer agent, J-107088, targeting topoisomerase I
    • Yoshinari, T.; Ohkubo, M.; Fukasawa, K.; Egashira, S.; Kara, Y. et al. Mode of action of a new indolocarbazole anticancer agent, J-107088, targeting topoisomerase I. Cancer Res. 1999, 59, 4271-4275.
    • (1999) Cancer Res. , vol.59 , pp. 4271-4275
    • Yoshinari, T.1    Ohkubo, M.2    Fukasawa, K.3    Egashira, S.4    Kara, Y.5
  • 12
    • 0032702777 scopus 로고    scopus 로고
    • In vivo antitumor activity of a novel indolocarbazole compound, J-107088, on murine and human tumors transplanted into mice
    • Arakawa, H.; Morita, M.; Kodera, T.; Okura, A.; Ohkubo, M. et al. In vivo antitumor activity of a novel indolocarbazole compound, J-107088, on murine and human tumors transplanted into mice. Jpn. J. Cancer Res. 1999, 90, 1163-1170.
    • (1999) Jpn. J. Cancer Res. , vol.90 , pp. 1163-1170
    • Arakawa, H.1    Morita, M.2    Kodera, T.3    Okura, A.4    Ohkubo, M.5
  • 13
    • 0034884824 scopus 로고    scopus 로고
    • Therapeutic activity of the topoisomerase I inhibitor J-107088 [6-N-(1-hydroxymethyla-2-hydroxy) ethylamino-12, 13-dihydro-13-(b-D-gluco pyranosyl)-5H-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5, 7(6H)-dione] against pediatric and adult central nervous system tumor xenografts
    • Cavazos, C.; Keir, S. T.; Yoshinari, T.; Bigner, D. D.; Friedman, H. S. Therapeutic activity of the topoisomerase I inhibitor J-107088 [6-N-(1-hydroxymethyla-2-hydroxy) ethylamino-12, 13-dihydro-13-(b-D-gluco pyranosyl)-5H-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5, 7(6H)-dione] against pediatric and adult central nervous system tumor xenografts. Cancer Chemother. Pharmacol. 2001, 48, 250-254.
    • (2001) Cancer Chemother. Pharmacol. , vol.48 , pp. 250-254
    • Cavazos, C.1    Keir, S.T.2    Yoshinari, T.3    Bigner, D.D.4    Friedman, H.S.5
  • 14
    • 0042121548 scopus 로고    scopus 로고
    • Rebeccamycin analogues bearing amine substituents or other groups on the sugar moiety
    • Anizon, F.; Moreau, P.; Sancelme, M.; Laine, W.; Bailly, C. et al. Rebeccamycin analogues bearing amine substituents or other groups on the sugar moiety. Bioorg. Med. Chem. 2003, 11, 3709-3722.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 3709-3722
    • Anizon, F.1    Moreau, P.2    Sancelme, M.3    Laine, W.4    Bailly, C.5
  • 15
    • 0034611438 scopus 로고    scopus 로고
    • Synthesis and biological activities of NB-506 analogues modified at the glucose group
    • Ohkubo, M.; Nishimura, T.; Kawamoto, H.; Nakano, M.; Honma, T. et al. Synthesis and biological activities of NB-506 analogues modified at the glucose group. Bioorg. Med. Chem. Lett. 2000, 10, 419-422.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 419-422
    • Ohkubo, M.1    Nishimura, T.2    Kawamoto, H.3    Nakano, M.4    Honma, T.5
  • 16
    • 0033049569 scopus 로고    scopus 로고
    • Enhanced binding to DNA and topoisomerase I inhibition by an analog of the antitumor antibiotic rebeccamycin containing an amino sugar residue
    • Bailly, C.; Qu, X.; Anizon, F.; Prudhomme, M.; Riou, J.-F. et al. Enhanced binding to DNA and topoisomerase I inhibition by an analog of the antitumor antibiotic rebeccamycin containing an amino sugar residue. Mol. Pharm. 1999, 55, 377-385.
    • (1999) Mol. Pharm. , vol.55 , pp. 377-385
    • Bailly, C.1    Qu, X.2    Anizon, F.3    Prudhomme, M.4    Riou, J.-F.5
  • 18
    • 0344131951 scopus 로고    scopus 로고
    • Learning nature's strategies for making deoxy sugars: Pathways, mechanisms, and combinatorial applications
    • Hallis, T. M.; Liu, H.-w. Learning nature's strategies for making deoxy sugars: pathways, mechanisms, and combinatorial applications. Acc. Chem. Res. 1999, 32, 579-588.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 579-588
    • Hallis, T.M.1    Liu, H.-W.2
  • 19
    • 0002334440 scopus 로고    scopus 로고
    • Chemical and biochemical aspects of deoxysugars and deoxysugar oligosaccharides
    • Kirschning, A.; Bechthold, A. F. W.; Rohr, J. Chemical and biochemical aspects of deoxysugars and deoxysugar oligosaccharides. Top. Curr. Chem. 1997, 188, 1-84.
    • (1997) Top. Curr. Chem. , vol.188 , pp. 1-84
    • Kirschning, A.1    Bechthold, A.F.W.2    Rohr, J.3
  • 20
    • 3843086796 scopus 로고    scopus 로고
    • Genes and enzymes involved in deoxysugar biosynthesis in bacteria
    • Trefzer, A.; Bechthold, A.; Salas, J. A. Genes and enzymes involved in deoxysugar biosynthesis in bacteria. Nat. Prod. Rep. 1999, 16, 283-299.
    • (1999) Nat. Prod. Rep. , vol.16 , pp. 283-299
    • Trefzer, A.1    Bechthold, A.2    Salas, J.A.3
  • 21
    • 0024333037 scopus 로고
    • AT2433-A1, AT2433-A2, AT2433-B1, and AT2433-B2 novel antitumor antibiotic compounds produced by Actinomadura melliaura. Taxonomy, fermentation, isolation and biological properties
    • Matson, J. A.; Claridge, C.; Bush, J. A.; Titus, J.; Bradner, W. T. et al. AT2433-A1, AT2433-A2, AT2433-B1, and AT2433-B2 novel antitumor antibiotic compounds produced by Actinomadura melliaura. Taxonomy, fermentation, isolation and biological properties. J. Antibiot. 1989, 42, 1547-1555.
    • (1989) J. Antibiot. , vol.42 , pp. 1547-1555
    • Matson, J.A.1    Claridge, C.2    Bush, J.A.3    Titus, J.4    Bradner, W.T.5
  • 22
    • 0033597875 scopus 로고    scopus 로고
    • Conformational control in the rebeccamycin class of indolocarbazole glycosides
    • Gilbert, E. J.; Chisholm, J. D.; Van Vranken, D. L. Conformational control in the rebeccamycin class of indolocarbazole glycosides. J. Org. Chem. 1999, 64, 5670-5676.
    • (1999) J. Org. Chem. , vol.64 , pp. 5670-5676
    • Gilbert, E.J.1    Chisholm, J.D.2    Van Vranken, D.L.3
  • 24
    • 0034304929 scopus 로고    scopus 로고
    • New synthesis of KT5823 indolocarbazole aglycone
    • Burtin, G. E.; Madge, D. J.; Selwood, D. L. New synthesis of KT5823 indolocarbazole aglycone. Heterocycles 2000, 53, 2119-2122.
    • (2000) Heterocycles , vol.53 , pp. 2119-2122
    • Burtin, G.E.1    Madge, D.J.2    Selwood, D.L.3
  • 26
    • 0037240829 scopus 로고    scopus 로고
    • A facile synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles via oxidative photocyclization of bisindolylmaleimides
    • Reddy, G. M.; Chen, S.-Y.; Uang, B.-J. A facile synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles via oxidative photocyclization of bisindolylmaleimides. Synthesis 2003, 497-500.
    • (2003) Synthesis , pp. 497-500
    • Reddy, G.M.1    Chen, S.-Y.2    Uang, B.-J.3
  • 27
    • 0037434589 scopus 로고    scopus 로고
    • Syntheses and antiproliferative activities of 7-azarebeccamycin analogues bearing one 7-azaindole moiety
    • Marminon, C.; Pierre, A.; Pfeiffer, B.; Perez, V.; Leonce, S. et al. Syntheses and antiproliferative activities of 7-azarebeccamycin analogues bearing one 7-azaindole moiety. J. Med. Chem. 2003, 46, 609-622.
    • (2003) J. Med. Chem. , vol.46 , pp. 609-622
    • Marminon, C.1    Pierre, A.2    Pfeiffer, B.3    Perez, V.4    Leonce, S.5
  • 30
    • 0027394116 scopus 로고
    • A stereoselective synthesis of indole-b-N-glycosides: An application to the synthesis of rebeccamycin
    • Gallant, M.; Link, J. T.; Danishefsky, S. J. A stereoselective synthesis of indole-b-N-glycosides: an application to the synthesis of rebeccamycin. J. Org. Chem. 1993, 58, 343-349.
    • (1993) J. Org. Chem. , vol.58 , pp. 343-349
    • Gallant, M.1    Link, J.T.2    Danishefsky, S.J.3
  • 31
    • 0033515622 scopus 로고    scopus 로고
    • Synthesis of rebeccamycin and 11-dechlororebeccamycin
    • Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. Synthesis of rebeccamycin and 11-dechlororebeccamycin. J. Org. Chem. 1999, 64, 2465-2470.
    • (1999) J. Org. Chem. , vol.64 , pp. 2465-2470
    • Faul, M.M.1    Winneroski, L.L.2    Krumrich, C.A.3
  • 32
    • 17944370005 scopus 로고    scopus 로고
    • Practical synthesis of a potent indolocarbazole-based DNA topoisomerase inhibitor
    • Akao, A.; Hiraga, S.; Ilida, T.; Kamatani, A.; Kawasaki, M. et al. Practical synthesis of a potent indolocarbazole-based DNA topoisomerase inhibitor. Tetrahedron 2001, 57, 8917-8923.
    • (2001) Tetrahedron , vol.57 , pp. 8917-8923
    • Akao, A.1    Hiraga, S.2    Ilida, T.3    Kamatani, A.4    Kawasaki, M.5
  • 33
    • 17144423732 scopus 로고    scopus 로고
    • Preparation of topoisomerase inhibitors indolocarbazole glycosides via phase transfer catalyzed glycosidation reaction
    • (Merck & Co., Inc., Rahway, NJ; Banyu Pharmaceutical Co., Ltd.). Wo; 46 pp
    • Petrillo, D. E.; Weissman, S. A.; Rossen, K.; Hiraga, S.; Satake, N. Preparation of topoisomerase inhibitors indolocarbazole glycosides via phase transfer catalyzed glycosidation reaction. PCT Int. Appl. (Merck & Co., Inc., Rahway, NJ; Banyu Pharmaceutical Co., Ltd.). Wo, 2002; 46 pp.
    • (2002) PCT Int. Appl.
    • Petrillo, D.E.1    Weissman, S.A.2    Rossen, K.3    Hiraga, S.4    Satake, N.5
  • 34
    • 0033530871 scopus 로고    scopus 로고
    • Synthesis and biological activities of NB-506 analogues: Effects of the positions of two hydroxyl groups at the indole rings
    • Ohkubo, M.; Nishimura, T.; Honma, T.; Nishimura, I.; Ito, S. et al. Synthesis and biological activities of NB-506 analogues: effects of the positions of two hydroxyl groups at the indole rings. Bioorg. Med. Chem. Lett. 1999, 3307, 7-3312.
    • (1999) Bioorg. Med. Chem. Lett. , vol.3307 , pp. 7-3312
    • Ohkubo, M.1    Nishimura, T.2    Honma, T.3    Nishimura, I.4    Ito, S.5
  • 35
    • 0000316365 scopus 로고
    • Synthesis of 2-deoxy sugars from glycals
    • Sabesan, S.; Neira, S. Synthesis of 2-deoxy sugars from glycals. J. Org. Chem. 1991, 56, 5468-5472.
    • (1991) J. Org. Chem. , vol.56 , pp. 5468-5472
    • Sabesan, S.1    Neira, S.2
  • 36
    • 17144371989 scopus 로고    scopus 로고
    • 5-Deoxy, 12-deoxy, 5,12-bisdeoxy, and 4, 5,12-trisdeoxy anthracyclines: Synthesis of new analogues of daunorubicin and doxorubicin by controlled deoxygenation of the C-ring
    • Cameron, D. W.; Feutrill, G. I,; Griffiths, P. G. 5-deoxy, 12-deoxy, 5,12-bisdeoxy, and 4, 5,12-trisdeoxy anthracyclines: synthesis of new analogues of daunorubicin and doxorubicin by controlled deoxygenation of the C-ring. Aust. J. Chem. 2000, 53, 25-40.
    • (2000) Aust. J. Chem. , vol.53 , pp. 25-40
    • Cameron, D.W.1    Feutrill, G.I.2    Griffiths, P.G.3
  • 37
    • 0023713928 scopus 로고
    • DNase I hypersensitivity is independent of endogenous topoisomerase II activity during chicken erythrocyte differentiation
    • Muller, M. T.; Mehta, V. B. DNase I hypersensitivity is independent of endogenous topoisomerase II activity during chicken erythrocyte differentiation. Mol. Cell. Biol. 1988, 8, 3661-3669.
    • (1988) Mol. Cell. Biol. , vol.8 , pp. 3661-3669
    • Muller, M.T.1    Mehta, V.B.2
  • 38
    • 0029041130 scopus 로고
    • Analysis of topoisomerase I/DNA complexes in patients administered topotecan
    • Subramanian, D.; Kraut, E.; Staubus, A.; Young, D. C.; Muller, M. T. Analysis of topoisomerase I/DNA complexes in patients administered topotecan. Cancer Res. 1995, 55, 2097-2103.
    • (1995) Cancer Res. , vol.55 , pp. 2097-2103
    • Subramanian, D.1    Kraut, E.2    Staubus, A.3    Young, D.C.4    Muller, M.T.5
  • 39
    • 0035219768 scopus 로고    scopus 로고
    • ICE bioassay. Isolating in vivo complexes of enzyme to DNA
    • Subramanian, D.; Furbee, C. S.; Muller, M. T. ICE bioassay. Isolating in vivo complexes of enzyme to DNA. Methods Mol. Biol. 2001, 95, 137-147.
    • (2001) Methods Mol. Biol. , vol.95 , pp. 137-147
    • Subramanian, D.1    Furbee, C.S.2    Muller, M.T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.