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Volumn 48, Issue 8, 2005, Pages 3085-3089

Potential antitumor agents. 37. Synthesis and antitumor activity of guanylhydrazones from imidazo[2,1-b]thiazoles and from the new heterocyclic system thiazolo[2′,3′:2,3]imidazo[4,5-c]quinoline

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 6 (2,5 DIMETHOXY 4 NITROPHENYL)IMIDAZO[2,1 B]THIAZOLE 5 CARBALDEHYDE; AMIDINOHYDRAZONE; IMIDAZO[2,1 B]THIAZOLE DERIVATIVE; QUINONE DERIVATIVE; THIAZOLO[2',3':2,3]IMIDAZO[4,5 C]QUINONE; UNCLASSIFIED DRUG;

EID: 20944432915     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040888s     Document Type: Article
Times cited : (86)

References (30)
  • 1
    • 2942679549 scopus 로고    scopus 로고
    • 2-[(E)-3-(6-Chloroimidazo[2,1-b]thiazol-5-yl)prop-2-enyl]-5, 6-dimethoxy-3-methyl-1,4-benzoquinone: A New Inhibitor of NADH Dehydrogenase with Antitumor Activity
    • Commemorative Issue in Honor of Prof. Vincenzo Tortorella
    • For part 36 see: Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Lenaz, G.; Fato, R.; Bergamini, C.: 2-[(E)-3-(6-Chloroimidazo[2,1-b]thiazol-5-yl)prop-2-enyl]-5, 6-dimethoxy-3-methyl-1,4-benzoquinone: a New Inhibitor of NADH Dehydrogenase with Antitumor Activity. Arkivoc 2004, Part V (Commemorative Issue in Honor of Prof. Vincenzo Tortorella), 76-84. http://www.arkat-usa.org/.
    • (2004) Arkivoc , Issue.PART V , pp. 76-84
    • Andreani, A.1    Granaiola, M.2    Leoni, A.3    Locatelli, A.4    Morigi, R.5    Rambaldi, M.6    Lenaz, G.7    Fato, R.8    Bergamini, C.9
  • 2
    • 0033869640 scopus 로고    scopus 로고
    • Potential antitumor agents. Part 29: Synthesis and potential coanthracyclinic activity of imidazo[2,1-b]thiazole guanylhydrazones
    • Andreani, A.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Recanatini, M.; Garaliene, V. Potential Antitumor Agents. Part 29: Synthesis and Potential Coanthracyclinic Activity of Imidazo[2,1-b]thiazole Guanylhydrazones. Bioorg. Med. Chem. 2000, 8, 2359-2366.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 2359-2366
    • Andreani, A.1    Leoni, A.2    Locatelli, A.3    Morigi, R.4    Rambaldi, M.5    Recanatini, M.6    Garaliene, V.7
  • 3
    • 1342271829 scopus 로고    scopus 로고
    • Potential antitumor agents. 34. Synthesis and antitumor activity of guanylhydrazones from imidazo[2, 1-b]thiazoles and from diimidazo[1,2-α: 1,2-c]pyrimidine
    • Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Giorgi, G.; Garaliene, V.: Potential Antitumor Agents. 34. Synthesis and Antitumor Activity of Guanylhydrazones from Imidazo[2, 1-b]thiazoles and from Diimidazo[1,2-α: 1,2-c]pyrimidine. Anticancer Res. 2004, 24, 203-214.
    • (2004) Anticancer Res. , vol.24 , pp. 203-214
    • Andreani, A.1    Granaiola, M.2    Leoni, A.3    Locatelli, A.4    Morigi, R.5    Rambaldi, M.6    Giorgi, G.7    Garaliene, V.8
  • 4
    • 0029974833 scopus 로고    scopus 로고
    • Potential antitumor agents. 24. Synthesis and pharmacological behaviour of imidazo[2, 1-b]thiazole guanylhydrazones bearing at least one chlorine
    • Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Bossa, R.; Fraccari, A.; Galatulas, I.; Salvatore, G. Potential Antitumor Agents. 24. Synthesis and Pharmacological Behaviour of Imidazo[2, 1-b]thiazole Guanylhydrazones Bearing at Least One Chlorine. J. Med. Chem. 1996, 39, 2852-2855.
    • (1996) J. Med. Chem. , vol.39 , pp. 2852-2855
    • Andreani, A.1    Rambaldi, M.2    Leoni, A.3    Locatelli, A.4    Bossa, R.5    Fraccari, A.6    Galatulas, I.7    Salvatore, G.8
  • 5
    • 0020623560 scopus 로고
    • Methylglyoxal-bis(guanylhydrazone) (Methyl-GAG): Current status and future prospects
    • Warrel, R. P., Jr; Burchenal, J. H. Methylglyoxal-Bis(Guanylhydrazone) (Methyl-GAG): Current Status and Future Prospects. J. Clin. Oncol. 1983, 1, 52-65.
    • (1983) J. Clin. Oncol. , vol.1 , pp. 52-65
    • Warrel Jr., R.P.1    Burchenal, J.H.2
  • 6
    • 0025164706 scopus 로고
    • Impaired mitochondrial respiration and stimulated glycolysis by m-iodobenzylguanidine (MIBG)
    • Loesberg, C.; Van Rooij, H.; Nooijen, W. J.; Meijer, A. J.; Smets, L. A. Impaired Mitochondrial Respiration and Stimulated Glycolysis by m-Iodobenzylguanidine (MIBG). Int. J. Cancer 1990, 46, 276-281.
    • (1990) Int. J. Cancer , vol.46 , pp. 276-281
    • Loesberg, C.1    Van Rooij, H.2    Nooijen, W.J.3    Meijer, A.J.4    Smets, L.A.5
  • 7
    • 0035874008 scopus 로고    scopus 로고
    • Guanidino-containing drugs in cancer chemotherapy: Biochemical and clinical pharmacology
    • Ekelund, S.; Nygren, P.; Larsson, R. Guanidino-containing Drugs in Cancer Chemotherapy: Biochemical and Clinical Pharmacology. Biochem. Pharmacol. 2001, 61, 1183-1193.
    • (2001) Biochem. Pharmacol. , vol.61 , pp. 1183-1193
    • Ekelund, S.1    Nygren, P.2    Larsson, R.3
  • 8
    • 0019411062 scopus 로고
    • Actions of bis(guanylhydrazones) on isolated rat liver mitochondria
    • Byczkowski, J. Z.; Salamon, W.; Harlos, J. P.; Porter, C. W. Actions of Bis(guanylhydrazones) on Isolated Rat Liver Mitochondria. Biochem. Pharmacol. 1981, 30, 2851-2860.
    • (1981) Biochem. Pharmacol. , vol.30 , pp. 2851-2860
    • Byczkowski, J.Z.1    Salamon, W.2    Harlos, J.P.3    Porter, C.W.4
  • 9
    • 0016740050 scopus 로고
    • On the mechanism of action of alkylguanidines on oxidative phosphorylation in mitochondria
    • Papa, S.; Tuena De Gómez-Puyou, M.; Gómez-Puyou, A. On the Mechanism of Action of Alkylguanidines on Oxidative Phosphorylation in Mitochondria. Eur. J. Biochem. 1975, 55, 1-8.
    • (1975) Eur. J. Biochem. , vol.55 , pp. 1-8
    • Papa, S.1    Tuena De Gómez-Puyou, M.2    Gómez-Puyou, A.3
  • 10
    • 0018743718 scopus 로고
    • Correlation of ultrastructural and functional damage to mitochondria of ascites L1210 cells treated in vivo with methylglyoxal-bis(guanylhydrazone) or ethidium bromide
    • Porter, C. W.; Mikles-Robertson, F.; Kramer, D.; Dave, C. Correlation of Ultrastructural and Functional Damage to Mitochondria of Ascites L1210 Cells Treated in Vivo with Methylglyoxal-Bis(guanylhydrazone) or Ethidium Bromide. Cancer Res. 1979, 39, 2414-2421.
    • (1979) Cancer Res. , vol.39 , pp. 2414-2421
    • Porter, C.W.1    Mikles-Robertson, F.2    Kramer, D.3    Dave, C.4
  • 11
    • 0022462195 scopus 로고
    • Aspects of the biochemical pharmacology of methyl glyoxal bis(guanylhydrazone)
    • Williams-Ashman, H. G.; Seidenfeld, J. Aspects of the Biochemical Pharmacology of Methyl glyoxal bis(guanylhydrazone). Biochem. Pharmacol. 1986, 35, 1217-1225.
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 1217-1225
    • Williams-Ashman, H.G.1    Seidenfeld, J.2
  • 14
    • 0017318125 scopus 로고
    • A convenient synthesis of quinones from hydroquinone dimethyl ethers. Oxidative demethylation with ceric ammonium nitrate
    • Jacob, P., 3rd; Gallery, P. S.; Shulgin, A. T.; Castagnoli, N., Jr. A Convenient Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Ceric Ammonium Nitrate. J. Org. Chem. 1976, 41, 3627-3629.
    • (1976) J. Org. Chem. , vol.41 , pp. 3627-3629
    • Jacob III, P.1    Gallery, P.S.2    Shulgin, A.T.3    Castagnoli Jr., N.4
  • 16
    • 17444374469 scopus 로고    scopus 로고
    • http://dtp.nci.nih.gov/docs/cancer/searches/standard_agent_table.html.
  • 17
    • 0035880254 scopus 로고    scopus 로고
    • Mitochondria! Membrane sensitivity to depolarization in acute myeloblastic leukemia is associated with spontaneous in vitro apoptosis, wild-type TP53, and vicinal thiol/disulfide status
    • Pallis, M.; Grundy, M.; Turzanski, J.; Kofler, R.; Russel, N. Mitochondria! Membrane Sensitivity to Depolarization in Acute Myeloblastic Leukemia is Associated with Spontaneous in Vitro Apoptosis, Wild-type TP53, and Vicinal Thiol/disulfide Status. Blood 2001, 98, 405-413.
    • (2001) Blood , vol.98 , pp. 405-413
    • Pallis, M.1    Grundy, M.2    Turzanski, J.3    Kofler, R.4    Russel, N.5
  • 18
    • 0037608698 scopus 로고    scopus 로고
    • CD40 triggering enhances fludarabine-induced apoptosis of chronic lymphocytic leukemia B-cells through autocrine release of tumor necrosis factor-α and interferon-γ and tumor necrosis factor receptor-I-II upregulation
    • de Totero, D.; Tazzari, P. L.; Capaia, M.; Montera, M. P.; Clavio. M.; Balleari, E.; Foa, R.; Gobbi, M. CD40 Triggering Enhances Fludarabine-induced Apoptosis of Chronic Lymphocytic Leukemia B-cells through Autocrine Release of Tumor Necrosis Factor-α and Interferon-γ and Tumor Necrosis Factor Receptor-I-II Upregulation. Haematologica 2003, 88, 148-158.
    • (2003) Haematologica , vol.88 , pp. 148-158
    • De Totero, D.1    Tazzari, P.L.2    Capaia, M.3    Montera, M.P.4    Clavio, M.5    Balleari, E.6    Foa, R.7    Gobbi, M.8
  • 19
    • 0028864003 scopus 로고
    • Discrimination of apoptotic thymocytes by forward light scatter
    • Ormerod, M. G.; Paul, F.; Cheetham, M.; Sun, X. M. Discrimination of Apoptotic Thymocytes by Forward Light Scatter. Cytometry 1995, 21, 300-304.
    • (1995) Cytometry , vol.21 , pp. 300-304
    • Ormerod, M.G.1    Paul, F.2    Cheetham, M.3    Sun, X.M.4
  • 20
    • 0026543962 scopus 로고
    • Analysis and discrimination of necrosis and apoptosis (programmed cell death) by multiparameter flow cytometry
    • Dive, C.; Gregory, C. D.; Phipps, D. J.; Evans, D. L.; Milner, A. E.; Wyllie, A. H. Analysis and Discrimination of Necrosis and Apoptosis (Programmed Cell Death) by Multiparameter Flow Cytometry. Biochim. Biophys. Acta 1992, 1133(3), 275-285.
    • (1992) Biochim. Biophys. Acta , vol.1133 , Issue.3 , pp. 275-285
    • Dive, C.1    Gregory, C.D.2    Phipps, D.J.3    Evans, D.L.4    Milner, A.E.5    Wyllie, A.H.6
  • 21
    • 0042526700 scopus 로고    scopus 로고
    • On the involvement of mitochondrial intermembrane junctional complexes in apoptosis
    • Crompton, M. On the Involvement of Mitochondrial Intermembrane Junctional Complexes in Apoptosis. Curr. Med. Chem. 2003, 10, 1473-1484.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 1473-1484
    • Crompton, M.1
  • 22
    • 0041810124 scopus 로고    scopus 로고
    • The mitochondrial Voltage-Dependent Anion Channel (VDAC) as a therapeutic target for initiating cell death
    • Granville, D. J.; Gottlieb, R. A. The Mitochondrial Voltage-dependent Anion Channel (VDAC) as a Therapeutic Target for Initiating Cell Death. Curr. Med. Chem. 2003, 10, 1527-1533.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 1527-1533
    • Granville, D.J.1    Gottlieb, R.A.2
  • 23
    • 0041809088 scopus 로고    scopus 로고
    • Bcl-2-related proteins as drug targets
    • O'Neill, J. W.; Hockenbery, D. M. Bcl-2-Related Proteins as Drug Targets. Curr. Med. Chem. 2003, 10, 1553-1562.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 1553-1562
    • O'Neill, J.W.1    Hockenbery, D.M.2
  • 24
    • 0344393075 scopus 로고    scopus 로고
    • Medicinal and genetic approaches to the treatment of mitochondrial disease
    • Schon E. A.; DiMauro, S. Medicinal and Genetic Approaches to the Treatment of Mitochondrial Disease. Curr. Med. Chem. 2003, 10, 2523-2533.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 2523-2533
    • Schon, E.A.1    DiMauro, S.2
  • 25
    • 0344393079 scopus 로고    scopus 로고
    • Mitochondria-targeting therapeutic strategies for overcoming chemoresistance and progression of cancer
    • Morisaki, T.; Katano, M. Mitochondria-Targeting Therapeutic Strategies for Overcoming Chemoresistance and Progression of Cancer. Curr. Med. Chem. 2003, 10, 2517-2521.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 2517-2521
    • Morisaki, T.1    Katano, M.2
  • 26
    • 0032496143 scopus 로고    scopus 로고
    • Superoxide in Apoptosis. Mitochondrial generation triggered by cytochrome c loss
    • Cai, J.; Jones, D. P. Superoxide in Apoptosis. Mitochondrial Generation Triggered by Cytochrome c Loss. J. Biol. Chem. 1998, 273, 11401-11404.
    • (1998) J. Biol. Chem. , vol.273 , pp. 11401-11404
    • Cai, J.1    Jones, D.P.2
  • 28
    • 0344393083 scopus 로고    scopus 로고
    • A multi-functional organelle mitochondrion is involved in cell death proliferation and disease
    • Ohta, S. A Multi-Functional Organelle Mitochondrion is Involved in Cell Death, Proliferation and Disease. Curr. Med. Chem. 2003, 10, 2485-2494.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 2485-2494
    • Ohta, S.1
  • 30
    • 0030856714 scopus 로고    scopus 로고
    • Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide
    • Gudz, T. I.; Tserng, K. Y.; Hoppel, C. L. Direct Inhibition of Mitochondrial Respiratory Chain Complex III by Cell-permeable Ceramide. J. Biol. Chem. 1997, 272, 24154-24158.
    • (1997) J. Biol. Chem. , vol.272 , pp. 24154-24158
    • Gudz, T.I.1    Tserng, K.Y.2    Hoppel, C.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.