메뉴 건너뛰기




Volumn 42, Issue 18, 1999, Pages 3494-3501

8,11-Dihydroxy-6-[(aminoalkyl)amino]-7H-benzo[e]perimidin-7-ones with activity in multidrug-resistant cell lines: Synthesis and antitumor evaluation

Author keywords

[No Author keywords available]

Indexed keywords

8,11 DIHYDROXY 6 [[2 (DIMETHYLAMINO)ETHYL]AMINO] 7H BENZO[E]PERIMIDIN 7 ONE HYDROCHLORIDE; ANTINEOPLASTIC AGENT; DOXORUBICIN; MITOXANTRONE; UNCLASSIFIED DRUG;

EID: 0033539129     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980682p     Document Type: Article
Times cited : (39)

References (38)
  • 2
    • 0020683314 scopus 로고
    • The design, synthesis and development of a new class of potent antineoplastic anthraquinones
    • (b) Cheng, C.; Zee-Cheng, R. K. Y. The Design, Synthesis and Development of a New Class of Potent Antineoplastic Anthraquinones. Prog. Med. Chem. 1983, 20, 83-118.
    • (1983) Prog. Med. Chem. , vol.20 , pp. 83-118
    • Cheng, C.1    Zee-Cheng, R.K.Y.2
  • 3
    • 0022637854 scopus 로고
    • Mitoxantrone: A new anticancer drug with significant clinical activity
    • (c) Shenkenberg, T. D.; Von Hoff, D. D. Mitoxantrone: A New Anticancer Drug with Significant Clinical Activity. Ann. Int. Med. 1986, 105, 67-81.
    • (1986) Ann. Int. Med. , vol.105 , pp. 67-81
    • Shenkenberg, T.D.1    Von Hoff, D.D.2
  • 4
    • 0023690467 scopus 로고
    • Mitoxantrone: A novel anthracycline derivative
    • (d) Koeller, J.; Eble, M. Mitoxantrone: A Novel Anthracycline Derivative. Clin. Pharm. 1988, 7, 574-581.
    • (1988) Clin. Pharm. , vol.7 , pp. 574-581
    • Koeller, J.1    Eble, M.2
  • 5
    • 0026127460 scopus 로고
    • Mitoxantrone. A review of its pharmacodinamic and pharmacokinetic properties, and therapeutic potential in the chemotherapy of cancer
    • (e) Faulds, D.; Balfour, J. A.; Chrisp, P.; Langtry, H. D. Mitoxantrone. A Review of its Pharmacodinamic and Pharmacokinetic Properties, and Therapeutic Potential in the Chemotherapy of Cancer. Drugs 1991, 41, 400-449.
    • (1991) Drugs , vol.41 , pp. 400-449
    • Faulds, D.1    Balfour, J.A.2    Chrisp, P.3    Langtry, H.D.4
  • 7
    • 0021271371 scopus 로고
    • Myocardial effects of mitoxantrone and doxorubicin in the mouse and guinea pig
    • (b) Perkins, W. E.; Schroeder, R. L.; Carrano, R. A.; Imondi, A. R. Myocardial Effects of Mitoxantrone and Doxorubicin in the Mouse and Guinea Pig. Cancer Treat. Rep. 1984, 68, 841-847.
    • (1984) Cancer Treat. Rep. , vol.68 , pp. 841-847
    • Perkins, W.E.1    Schroeder, R.L.2    Carrano, R.A.3    Imondi, A.R.4
  • 8
    • 0025314760 scopus 로고
    • Structure - Activity relationships of antineoplastic agents in multidrug resistance
    • (a) Selassie, C. D.; Hansch, C.; Khwaja, T. A. Structure - Activity Relationships of Antineoplastic Agents in Multidrug Resistance. J. Med. Chem. 1990, 33, 1914-1919.
    • (1990) J. Med. Chem. , vol.33 , pp. 1914-1919
    • Selassie, C.D.1    Hansch, C.2    Khwaja, T.A.3
  • 10
    • 0024329881 scopus 로고
    • The biochemistry of P-glycoprotein-mediated multidrug resistance
    • (c) Endicott, J. A.; Ling, V. The Biochemistry of P-Glycoprotein-Mediated Multidrug Resistance. Annu. Rev. Biochem. 1989, 58, 137-171.
    • (1989) Annu. Rev. Biochem. , vol.58 , pp. 137-171
    • Endicott, J.A.1    Ling, V.2
  • 11
    • 0025947620 scopus 로고
    • Synthesis and antitumor evaluation of symmetrically and unsymmetrically substituted 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones and 1,4-bis[(aminoalkyl)amino]-5,8-dihydroxy-anthracene-9,10-diones
    • Krapcho, A. P.; Getahun, Z.; Avery, K. L., Jr.; Vargas, K. J.; Hacker, M. P.; Spinelli, S.; Pezzoni, G.; Manzotti, C. Synthesis and Antitumor Evaluation of Symmetrically and Unsymmetrically Substituted 1,4-Bis[(aminoalkyl)amino]anthracene-9,10-diones and 1,4-Bis[(aminoalkyl)amino]-5,8-dihydroxy-anthracene-9,10-diones. J. Med. Chem. 1991, 34, 2373-2380.
    • (1991) J. Med. Chem. , vol.34 , pp. 2373-2380
    • Krapcho, A.P.1    Getahun, Z.2    Avery K.L., Jr.3    Vargas, K.J.4    Hacker, M.P.5    Spinelli, S.6    Pezzoni, G.7    Manzotti, C.8
  • 13
    • 0029016102 scopus 로고
    • Chromophore-modified antitumor anthracenediones: Synthesis, DNA binding, and cytotoxic acivity of 1,4-bis[(aminoalkyl)amino]benzo[g]-phthalazine-5,10-diones
    • Gandolfi, C. A.; Beggiolin, G.; Menta, E.; Palumbo, M.; Sissi, C.; Spinelli, S.; Johnson, F. Chromophore-Modified Antitumor Anthracenediones: Synthesis, DNA Binding, and Cytotoxic Acivity of 1,4-Bis[(aminoalkyl)amino]benzo[g]-phthalazine-5,10-diones. J. Med. Chem. 1995, 38, 526-536.
    • (1995) J. Med. Chem. , vol.38 , pp. 526-536
    • Gandolfi, C.A.1    Beggiolin, G.2    Menta, E.3    Palumbo, M.4    Sissi, C.5    Spinelli, S.6    Johnson, F.7
  • 16
    • 0022449184 scopus 로고
    • Resistance to anthrapyrazoles and anthracyclines in multidrug-resistant P388 murine leukemia cells: Reversal by calcium blockers and calmodulin antagonists
    • (c) Klohs, W. D.; Steinkampf, R. W.; Havlick, M. J.; Jackson, R. C. Resistance to Anthrapyrazoles and Anthracyclines in Multidrug-resistant P388 Murine Leukemia Cells: Reversal by calcium Blockers and Calmodulin Antagonists. Cancer Res. 1986, 46, 4352-4356.
    • (1986) Cancer Res. , vol.46 , pp. 4352-4356
    • Klohs, W.D.1    Steinkampf, R.W.2    Havlick, M.J.3    Jackson, R.C.4
  • 18
    • 24244464489 scopus 로고    scopus 로고
    • Unpublished data
    • (a) Stefańska, B. Unpublished data.
    • Stefańska, B.1
  • 20
    • 0025165116 scopus 로고
    • 5-[(aminoalkyl)amino]imidazo[4,5,1-de]acridine-6-ones as a novel class of antineoplastic agents: Synthesis and biologcal activity
    • (a) Cholody, W. M.; Martelli, S.; Paradziej-Lukowicz, J.; Konopa, J. 5-[(Aminoalkyl)amino]imidazo[4,5,1-de]acridine-6-ones as a Novel Class of Antineoplastic Agents: Synthesis and Biologcal Activity. J. Med. Chem. 1990, 33, 49-52.
    • (1990) J. Med. Chem. , vol.33 , pp. 49-52
    • Cholody, W.M.1    Martelli, S.2    Paradziej-Lukowicz, J.3    Konopa, J.4
  • 21
    • 0029927340 scopus 로고    scopus 로고
    • Pharmacological and toxicological aspects of new imidazoacridinone antitumor agents
    • (b) Berger, B.; Marquardt, H.; Westendorf, J. Pharmacological and Toxicological Aspects of New Imidazoacridinone Antitumor Agents. Cancer Res. 1996, 56, 2094-2104.
    • (1996) Cancer Res. , vol.56 , pp. 2094-2104
    • Berger, B.1    Marquardt, H.2    Westendorf, J.3
  • 22
    • 0025184313 scopus 로고
    • 8-substituted 5-[(aminoalkyl)amino]-6H-v-triazolo[4,5,1-de]acidin-6-ones as potential antineoplastic agents. Synthesis and biological activity
    • (a) Chotody, W. M.; Martelli, S.; Konopa, J. 8-Substituted 5-[(Aminoalkyl)amino]-6H-v-triazolo[4,5,1-de]acidin-6-ones as Potential Antineoplastic Agents. Synthesis and Biological Activity. J. Med. Chem. 1990, 33, 2852-2856.
    • (1990) J. Med. Chem. , vol.33 , pp. 2852-2856
    • Chotody, W.M.1    Martelli, S.2    Konopa, J.3
  • 25
    • 0029135131 scopus 로고
    • Synthesis of (dialkylamino)alkyl-disubstituted pyrimido[5,6,1-de]acridines, a novel group of anticancer agents active on a multidrug resistant cell line
    • Antonini, I.; Cola, D.; Polucci, P.; Bontemps-Gracz, M.; Borowski, E.; Martelli, S. Synthesis of (Dialkylamino)alkyl-disubstituted Pyrimido[5,6,1-de]acridines, a Novel Group of Anticancer Agents Active on a Multidrug Resistant Cell Line. J. Med. Chem. 1995, 38, 3282-3286.
    • (1995) J. Med. Chem. , vol.38 , pp. 3282-3286
    • Antonini, I.1    Cola, D.2    Polucci, P.3    Bontemps-Gracz, M.4    Borowski, E.5    Martelli, S.6
  • 26
    • 0027458425 scopus 로고
    • 6-[(Aminoalkyl)amino]-substituted 7H-benzo[e]perimidin-7-ones as novel antineoplastic agents. Synthesis and biological evaluation
    • Stefańska, B.; Dzieduszycka, M.; Martelli, S.; Tarasiuk, J.; Bontemps-Gracz, M.; Borowski, E. 6-[(Aminoalkyl)amino]-Substituted 7H-Benzo[e]perimidin-7-ones as Novel Antineoplastic Agents. Synthesis and Biological Evaluation. J. Med. Chem. 1993, 36, 38-41.
    • (1993) J. Med. Chem. , vol.36 , pp. 38-41
    • Stefańska, B.1    Dzieduszycka, M.2    Martelli, S.3    Tarasiuk, J.4    Bontemps-Gracz, M.5    Borowski, E.6
  • 27
    • 0026695303 scopus 로고
    • The essential role of anthraquinones as substrates for NADH dehydrogenase in their redox cycling activity
    • Tarasiuk, J.; Garnier-Suillerot, A.; Stefańska, B.; Borowski, E. The Essential Role of Anthraquinones as Substrates for NADH Dehydrogenase in Their Redox Cycling Activity. Anti-Cancer Drug Des. 1992, 7, 329-340.
    • (1992) Anti-cancer Drug Des. , vol.7 , pp. 329-340
    • Tarasiuk, J.1    Garnier-Suillerot, A.2    Stefańska, B.3    Borowski, E.4
  • 28
    • 0026602257 scopus 로고
    • Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias
    • Chołody, W. M.; Martelli, S.; Konopa, J. Chromophore-Modified Antineoplastic Imidazoacridinones. Synthesis and Activity Against Murine Leukemias. J. Med. Chem. 1992, 35, 378-382.
    • (1992) J. Med. Chem. , vol.35 , pp. 378-382
    • Chołody, W.M.1    Martelli, S.2    Konopa, J.3
  • 29
    • 0030748628 scopus 로고    scopus 로고
    • Facile and efficient synthesis of 7,10-dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one via hypervalent iodine oxidation
    • Kato, N.; Sugaya, T.; Mimura, T.; Ikuta, M.; Kato, S.; Kuge, Y.; Tomioka, S.; Kasai, M. Facile and Efficient Synthesis of 7,10-Dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one via Hypervalent Iodine Oxidation. Synthesis 1997, 625-627.
    • (1997) Synthesis , pp. 625-627
    • Kato, N.1    Sugaya, T.2    Mimura, T.3    Ikuta, M.4    Kato, S.5    Kuge, Y.6    Tomioka, S.7    Kasai, M.8
  • 30
    • 21344478015 scopus 로고
    • Synthesis of 1,4 diamino-5,8-dihydroxy-9,10-anthracenedione via gabriel reaction
    • Dzieduszycka, M.; Stefańska, B.; Borowski, E. Synthesis of 1,4 Diamino-5,8-dihydroxy-9,10-anthracenedione via Gabriel Reaction. Pol. J. Chem. 1994, 68, 1669-1671.
    • (1994) Pol. J. Chem. , vol.68 , pp. 1669-1671
    • Dzieduszycka, M.1    Stefańska, B.2    Borowski, E.3
  • 31
    • 0027267217 scopus 로고
    • Anticancer anthrapyrazoles. The synthesis of 2-substituted 5-nitro and 5-aminoanthra[1,9-cd]pyrazol-6(2H)-ones
    • Showalter, H. D. H.; Turner, W. R. Anticancer Anthrapyrazoles. The Synthesis of 2-Substituted 5-Nitro and 5-Aminoanthra[1,9-cd]pyrazol-6(2H)-ones. J. Heterocycl. Chem. 1993, 30, 493-496.
    • (1993) J. Heterocycl. Chem. , vol.30 , pp. 493-496
    • Showalter, H.D.H.1    Turner, W.R.2
  • 32
    • 0024376418 scopus 로고
    • Biological evaluation of mitoxantrone dihydrochloride synthesized by a new methodol. I. Acute toxicity and antitumor activity in mouse transplantable tumor systems
    • Matuszyk, J.; Kuœnierczyk, H.; Radzikowski, C. Biological Evaluation of Mitoxantrone Dihydrochloride Synthesized by a New Methodol. I. Acute Toxicity and Antitumor Activity in Mouse Transplantable Tumor Systems. Arch. Immunol. Ther. Exp. 1989, 37, 77-87.
    • (1989) Arch. Immunol. Ther. Exp. , vol.37 , pp. 77-87
    • Matuszyk, J.1    Kuœnierczyk, H.2    Radzikowski, C.3
  • 34
    • 0032409725 scopus 로고    scopus 로고
    • The role of structural factors of anthraquinones and their heteroatomic analogues in NADH dehydrogenase catalysed oxygen radical formation
    • Tarasiuk, J.; Tkaczyk-Gobis, K.; Stefańska, B.; Dzieduszycka, M.; Priebe, W.; Martelli, S.; Borowski, E. The Role of Structural Factors of Anthraquinones and Their Heteroatomic Analogues in NADH Dehydrogenase Catalysed Oxygen Radical Formation. Anti-Cancer Drug Des. 1998, 13, 923-939.
    • (1998) Anti-cancer Drug Des. , vol.13 , pp. 923-939
    • Tarasiuk, J.1    Tkaczyk-Gobis, K.2    Stefańska, B.3    Dzieduszycka, M.4    Priebe, W.5    Martelli, S.6    Borowski, E.7
  • 35
    • 0026281051 scopus 로고
    • The influence of L-norvalyl-N3-4-methoxyfumaroyl-L-2,3-diaminopropanoic acid, an antifungal agent, on mammalian cells in tissue culture
    • Bontemps-Gracz, M.; Milewski, S.; Borowski, E. The Influence of L-Norvalyl-N3-4-methoxyfumaroyl-L-2,3-diaminopropanoic Acid, an Antifungal Agent, on Mammalian Cells in Tissue Culture. Acta Biochim. Pol. 1991, 38, 229-239.
    • (1991) Acta Biochim. Pol. , vol.38 , pp. 229-239
    • Bontemps-Gracz, M.1    Milewski, S.2    Borowski, E.3
  • 36
    • 0002265018 scopus 로고
    • Protocols for screening chemical agents and natural products against animal tumors and other biological systems
    • (a) Geran, R. I.; Greenberg, N. H.; Macdonald, M. M.; Schumacher, A. M.; Abbott, B. J. Protocols for Screening Chemical Agents and Natural Products Against Animal Tumors and Other Biological Systems. Cancer Chemother. Rep. 1972, 3, 1-88.
    • (1972) Cancer Chemother. Rep. , vol.3 , pp. 1-88
    • Geran, R.I.1    Greenberg, N.H.2    Macdonald, M.M.3    Schumacher, A.M.4    Abbott, B.J.5
  • 37
    • 0344896287 scopus 로고
    • NIH Publication No. 84-2635
    • (b) In vivo Cancer Models; NIH Publication No. 84-2635, 1984; p 27.
    • (1984) In Vivo Cancer Models , pp. 27
  • 38
    • 0022448097 scopus 로고
    • Isolation and characterization of a human colon adenocarcinoma cell line resistant to doxorubicin
    • Grandi, M.; Geroni, C.; Giuliani, F. C. Isolation and Characterization of a Human Colon Adenocarcinoma Cell Line Resistant to Doxorubicin. Br. J. Cancer 1986, 54, 515-518.
    • (1986) Br. J. Cancer , vol.54 , pp. 515-518
    • Grandi, M.1    Geroni, C.2    Giuliani, F.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.