Novel 5-aminoflavone derivatives as specific antitumor agents in breast cancer

Journal of Medicinal Chemistry

Volumn 39, Issue 18, 1996, Pages 3461-3469

  Akama, Tsutomu ^a   Shida, Yasushi ^a   Sugaya, Toru ^a   Ishida, Hiroyuki ^a   Gomi, Katsushige ^a   Kasai, Masaji ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR; FLAVONE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING COMPETITION; BREAST CANCER; CANCER CELL CULTURE; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; RECEPTOR BINDING;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; ESTRADIOL; FEMALE; FLAVONOIDS; HELA CELLS; HUMANS; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0029792884     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950938g     Document Type: Article

References (48)

1. McGuire, W. L. Hormone Receptors: Their Role in Predicting Prognosis and Response to Endocrine Therapy. Semin. Oncol. 1978, 5, 428-433.
2. Miller, W. R. Endocrine Treatment for Breast Cancers: Biological Rationale and Current Progress. J. Steroid Biochem. Mol. Biol. 1990, 37, 467-480.
3. Jordan, V. C. Biochemical Pharmacology of Antiestrogen Action. Pharmacol. Rev. 1984, 36 (4), 245-276.
4. Magarian, R. A.; Overacre, L. B.; Singh, S.; Meyer, K. L. The Medicinal Chemistry of Nonsteroidal Antiestrogens: A Review. Curr. Med. Chem. 1994, 1, 61-104.
5. Jordan, V. C. The Strategic Use of Antiestrogens to Control the Development and Growth of Breast Cancer. Cancer 1992, 70, 977-982.
6. Thompson, E. W.; Katz, D.; Shima, T. B.; Wakeling, A. E.; Lippman, M. E.; Dickson, R. B. ICI 164384, a Pure Antagonist of Estrogen-stimulated MCF-7 Cell Proliferation and Invasiveness. Cancer Res. 1989, 49, 6929-6934.
7. Jones, C. D.; Blaszczak, L. C.; Goettel, M. E.; Suarez, T.; Crowell, T. A.; Mabry, T. E.; Ruenitz, P. C.; Srivatsan, V. Antiestrogens. 3. Estrogen Receptor Affinities and Antiproliferative Effects in MCF-7 Cells of Phenolic Analogues of Trioxifene, [3,4-Dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl)-ethoxy] phenyl]methanone. J. Med. Chem. 1992, 35, 931-938.
8. Angerer, E. V.; Knebel, N.; Kager, M.; Ganss, B. 1-(Aminoalkyl)-2-phenylindoles as Novel Pure Estrogen Antagonists. J. Med. Chem. 1990, 33, 2635-2640.
9. Velde, P. V.; Nique, F.; Bremaud, J.; Hameau, M.-C.; Lucas, D.; Moratille, C.; Viet, D.; Teutsch, G. RU 58668, a New Pure Antiestrogen Including a Regression of Human Mammary Carcinoma Implanted in Nude Mice. J. Steroid Biochem. Mol. Biol. 1994, 48 (2/3), 187-196.
10. Poirier, D.; Auger, S.; Merand, Y.; Simard, J.; Labrie, F. Synthesis and Antiestrogenic Activity of Diaryl Thioether Derivatives. J. Med. Chem. 1994, 37, 1115-1125.
11. Allegra, J. C.; Lippman, M. E.; Thompson, E. B.; Simon, R.; Barlock, A.; Green, L.; Huff, K. F.; Do, H. M. T.; Aitken, S. C.; Warren, R. Estrogen Receptor Status: an Important Variable in Predicting Response to Endocrine Therapy in Metastatic Breast Cancer. Eur. J. Cancer 1980, 16, 323-331.
12. Murdoch, F. E.; Fritsch, M.; Gorski, J. The Estrogen Receptor: Mechanism of Action and Relationship to Human Breast Cancer. ISI Atlas Sci.: Pharmacol. 1988, 2 (3), 267-275.
13. Jozan, S.; Julia, A.-M.; Carretie, A.; Eche, N.; Maisongrosse, V.; Fouet, B.; Marques, B.; David, F. 65 and 47 kDa Forms of Estrogen Receptor in Human Breast Cancer: Relation with Estrogen Responsiveness. Breast Cancer Res. Treat. 1991, 19, 103-109.
14. Vijver, M. J.; Nusse, R. The Molecular Biology of Breast Cancer. Biochem. Biophys. Acta 1991, 1072, 33-50.
15. Kurebayashi, J.; Kurosumi, M.; Sonoo, H. A New Human Breast Cancer Cell Line, KPL-1 Secretes Tumor-Associated Antigens and Grows Rapidly in Female Athymic Nude Mouse. Br. J. Cancer 1995, 71, 845-853.
16. Middleton, E.; Kandaswami, C. The Impact of Plant Flavonoids on Mammalian Biology: Implications for Immunity, Inflammation and Cancer. In The Flavonoids Advances in Research Since 1986; Harborne, J. B., Ed.; Chapman & Hall: London, 1994; pp 619-652.
17. Simpson, T. H.; Uri, N. Hydroxyflavones as Inhibitors of the Aerobic Oxidation of Unsaturated Fatty Acids. Chem. Ind. 1956, 956-957.
18. Ito, M.; Ishimoto, S.; Nishida, Y.; Shiramizu, T.; Yunoki, H. Effects of Baicalein, a Flavonoid, and Other Anti-inflammatory Agents on Glyoxalase-I Activity. Agric. Biol. Chem. 1986, 50, 1073-1074.
19. Ares, J. J.; Outt, P. E.; Randall, J. L.; Murray, P. D.; Weisshaar, P. S.; O'Brien, L. M.; Ems, B. L.; Kakodkar, S. V.; Kelm, G. R.; Kershaw, W. C.; Werchowski, K. M.; Parkinson, A. Synthesis and Biological Evaluation of Substituted Flavones as Gastroprotective Agents. J. Med. Chem. 1995, 38, 4937-4943.
20. Meyer, N. D.; Haemers, A.; Mishra, L.; Pandey, H.-K.; Pieters, L. A. C.; Berghe, D. A. V.; Vlietinck, A. 4′-Hydroxy-3-methoxy-flavones with Potent Antipicornavirus Activity. J. Med. Chem. 1991, 34, 736-746.
21. Wall, M. E.; Wani, M. C.; Manikumar, G.; Abraham, P.; Taylor, H.; Hughes, T. J.; Warner, J.; McGivney, R. Plant Antimutagenic Agents, 2. Flavonoids. J. Nat. Prod. 1988, 51, 1084-1091.
22. Yamashita, Y.; Kawada, S.; Nakano, H. Induction of Mammalian Topoisomerase II Dependent DNA Cleavage by Nonintercalative Flavonoids, Genistein and Orobol. Biochem. Pharmacol. 1990, 39, 737-744.
23. Ferriola, P.; Cody, V.; Middleton, E., Jr. Protein Kinase C Inhibition by Plant Flavonoids. Biochem. Pharmacol. 1989, 38, 1617-1624.
24. Hayashi, T.; Uchida, K.; Hayashi, K.; Niwayama, S.; Morita, N. A Cytotoxic Flavone from Scoparia dulcis L. Chem. Pharm. Bull. 1988, 36, 4849-4851.
25. Double, J. A.; Bibby, M. C.; Loadman, P. M. Pharmacokinetics and Antitumor Activity of LM985 in Mice Bearing Transplantable Adenocarcinomas of the Colon. Br. J. Cancer 1986, 54, 595-600.
26. Beutler, J. A.; Cardellina, J. H., II; Lin, C. M.; Hamel, E.; Cragg, G. M.; Boyd, M. R. Centaureidin, A Cytotoxic Flavone from Polymnia fruticosa, Inhibits Tubulin Polymerization. Bioorg. Med. Chem. Lett. 1993, 3, 581-584.
27. Hirano, T.; Oka, K.; Akiba, M. Antiproliferative Effects of Synthetic and Naturally Occurring Flavonoids on Tumor Cells of Human Breast Carcinoma Cell Line, ZR-75-1. Res. Commun. Chem. Pathol. Pharmacol. 1989, 64 (1), 69-78.
28. Ibrahim, A.-R.; Abul-Haji, Y. J. Aromatase Inhibition by Flavonoids. J. Steroid Biochem. Mol. Biol. 1990, 37 (2), 257-260.
29. Kondo, H.; Nakajima, S.; Yamamoto, N.; Okura, A.; Satoh, F.; Suda, H.; Okanishi, M.; Tanaka, N. BE-14348 Substances, New Specific Estrogen-receptor Binding Inhibitors. Production, Isolation, Structure Determination and Biological Properties. J. Antibiot. 1990, 43 (12), 1533-1542.
30. Cheng, E.; Yoder, L.; Story, C. D.; Burroughs, W. Estrogenic Activity of Some Isoflavone Derivatives. Science 1954, 720, 575-576.
31. Kaur, G.; Stetler-Stevenson, M.; Sebers, S.; Worland, P.; Sedlacek, H.; Myers, C.; Czech, J.; Naik, R.; Sausville, E. Growth Inhibition with Reversible Cell Cycle Arrest of Carcinoma Cells by Flavone L86-8275. J. Natl. Cancer Inst. 1992, 84, 1736-1740.
32. Jesth, P. K.; Behera, Y. Antispasmodics and Antihistaminics Derived from Amino Flavones. J. Inst. Chem. (India) 1981, 53, 234-236.
33. Vijaya, L. M.; Subba, R. N. V. Synthesis of 7-Aminoflavones as Potential Bactericides. Curr. Sci. 1967, 36 (15), 401-402.
34. Kumari, S. S.; Rao, K. S. R. K. M.; Rao, N. V. S. Search for Physiologically Active Compounds. Proc. Indian Acad. Sci., Sect. A 1969, 69 (2), 88-93.
35. Cushman, M.; Nagarathnam, D.; Burg, D. L.; Geahlen, R. L. Synthesis and Protein-Tyrosine Kinase Inhibitory Activities of Flavonoid Analogues. J. Med. Chem. 1991, 34, 798-806.
36. Eiden, F.; Patzelt, G.; Buchborn, H. Benzolderivate aus Pyranen: 5-Aminochromone und -Flavone aus 3-Acetyl-2,6-dimethyl-4H-pyran-4-one. (Pyran derivatives. 127. Benzene derivatives of pyrans: 5-aminochromones and -flavones from 3-acetyl-2,6-dimethyl-4H-pyran-4-one.) Arch. Pharm. (Weinheim, Ger.) 1989, 322, 589-592.
37. u-src. J. Med. Chem. 1994, 37, 3353-3362.
38. Sugaya, T.; Mimura, Y.; Kato, N.; Ikuta, M.; Mimura, T.; Kasai, M.; Tomioka, S. Synthesis of 6H-Pyrazolo[4,5,1-de]acridin-6-one Derivative: A Useful Intermediate of Antitumor Agents. Synthesis 1994, 73-76.
39. Chang, C. T.; Chen, F. C.; Chen, T. S.; Hsu, K. K.; Ueng, T.; Hung, M. Synthesis of 6-Halogenoflavones and Related Compounds. J. Chem. Soc. 1961, 3414-3417.
40. Smith, F. E. A New Preparation of 7:8-Benzoflavone (α-Naphthaflavone). J. Chem. Soc. 1946, 542.
41. Scholl, S. M.; Huff, K. K.; Lippman, M. E. Antiestrogen Action of LY 117018 in MCF-7 Cells. Endocrinology 1983, 113, 611-617.
42. Furr, B. J. A.; Jordan, V. C. The Pharmacology and Clinical Uses of Tamoxifen. Pharmacol. Ther. 1984, 25, 127-205.
43. Denton, R. R.; Koszewski, N. J.; Notides, A. C. Estrogen receptor Phosphorylation. J. Biol. Chem. 1992, 267 (11), 7263-7268.
44. Ali, S.; Metzger, D.; Bornert, J.-M.; Chambon, P. Modulation of Transcriptional Activation by Ligand-dependent Phosphorylation of the Human Oestrogen Receptor A/B Region. EMBO J. 1993, 12 (3), 1153-1160.
45. Goff, P. L.; Montano, M. M.; Schodin, D. J.; Katzenellenbogens, B. S. Phosphorylation of the Human Estrogen Receptor. J. Biol. Chem. 1994, 269 (6), 4458-4466.
46. Lahooti, H.; White, R.; Danielian, P. S.; Parker, M. G. Characterization of Ligand-Dependent Phosphorylation of the Estrogen Receptor. Mol. Endocrinol. 1994, 8, 182-188.
47. Loziewicz, M. D.; Carlson, B. A.; Kaur, G.; Sausville, E. A.; Worland, P. J. Potent Inhibition of Cdc2 Kinase Activity by the Flavonoid L86-8275. Biochem. Biophys. Res. Commun. 1994, 201 (2), 589-595.
48. Czech, J.; Hoffman, D.; Naik, R.; Sedlacek, H.-H. Antitumoral Activity of Flavone L 86-8275. Int. J. Cancer 1995, 6, 31-36.