Synthesis and antitumor cytotoxicity evaluation of pyrido[4,3,2-de]quinolines and isoquinolino[6,5,4,3-cde]quinolines

Anti-Cancer Drug Design

Volumn 15, Issue 2, 2000, Pages 99-108

  Ding, Qizhu ^a   Jia, Guofeng ^a   Lown, J William ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Antitumor; In vitro cytotoxicity; Isoquinolino 6,5,4,3 cde quinolines; Pyrido 4,3,2 de quinolines

Indexed keywords

ACETOACETIC ACID; ACETOPHENONE; ANISOLE; PYRIDONE DERIVATIVE; QUINOLINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CELL STRAIN HL 60; CONTROLLED STUDY; CRYSTAL; CYCLIZATION; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; LUNG NON SMALL CELL CANCER; OXIDATION; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; CARCINOMA, NON-SMALL-CELL LUNG; CELL DIVISION; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HL-60 CELLS; HUMANS; ISOQUINOLINES; LEUKEMIA; LUNG NEOPLASMS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

VIOLA (ANGIOSPERM);

EID: 0034118561     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. Abell A.D., Blunt J.W., Foulds G.J., Munro M.H.G. (1997) Chemistry of the mycalamides: antiviral and antitumor compounds from a New Zealand marine sponge. Part 6. The synthesis and testing of analogs of the C(7)-C(10) fragment. Journal of the Chemistry Society, Perkin Transactions 1, 1647.
2. Boyd M.R., Paull K.D. (1995) Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Development Research, 34, 91.
3. Boyd M.R., Paull K.D., Rubinstein L.R. (1992) In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery. Valeriote F.A., Corbett T., Baker L. (eds), p. 11. Kluwer Academic Publishers: Amsterdam.
4. Davidson B.S. (1993) Ascidians: producers of amino acid derived metabolites. Chemical Reviews, 93, 1771.
5. Ding Q.Z., Lown J.W. (1998a) Reactions of 1H-2,3-diketopyrido[4,3,2-de]quinoline with acetone and acetophenone: a novel synthesis of the isoquinolino[6,5,4,3-cde]quinoline nucleus. Heterocyclic Communications, 4, 535.
6. Ding Q.Z., Lown J.W. (1998b) Synthesis of a pyrido[4,3,2-de]quinoline nucleus: a derivative of the discohabdin alkaloids. Heterocyclic Communications, 4, 125.
7. Ding Q.Z., Lown J.W. (1999) Novel amination and 1,2-amino, hydro-elimination between 2,3-diketopyrido[4,3,2-de]-quinolines and primary amino compounds, The Journal of Organic Chemistry, 64, 7965.
8. Ding Q.Z., Zhao R.L., Lown J.W. (1997) Synthesis of a furo-[4,3,2-de]quinoline nucleus: a derivative of the discohabdin alkaloids. Heterocyclic Communications, 3, 489.
9. Ding Q.Z., Chichak K., Lown J.W. (1999) Pyrroloquinoline and pyridoacridine alkaloids from marine sources. Current Medicinal Chemistry, 6, 1.
10. Doughty S.W., Blaney F.E., Orlek B.S., Richards W.G. (1998) A molecular mechanism for toxin block in N-type calcium channels. Protein Engineering, 11, 95.
11. Ede C., Schupp P., Proksch P., Wray V., Steube K., Muller C.E., Frobenius W., Herderich M., Van Soest R.W.M. (1998) Bioactive pyridoacridine alkaloids from the micronesian sponge oceanapia sp. Journal of Natural Products, 61, 301.
12. England L.J., Imperial J., Jacobsen R., Craig A.G., Gulyas J., Akhtar M., Rivier J., Julius D., Olivera B.M. (1989) Inactivation of a serotonin-gated ion channel by a polypeptide toxin from marine snails. Science, 281, 575.
13. Glisson B.S., Ross W.E. (1987) DNA topoisomerase II: a primer on the enzyme and its unique role as a multidrug target in cancer chemotherapy. Pharmacology and Therapeutics, 32, 89.
14. Hagan D.J., Gimenez-Arnau E., Schwalbe C.H., Stevens M.F.J. (1997) Antitumor polycyclic acridines. Part 1. Synthesis of 7H-pyrido- and 8H-quino-[4,3,2-kl]acridines by Graebe-Ullmann thermolysis of 9-(1,2,3-triazol-1-yl)acridines: application of differential scanning calorimetry to predict optimum cyclisation conditions. Journal of the Chemistry Society, Perkin Transactions 1, 2739.
15. Hagan D.J., Chan D., Schwalbe C.H., Stevens M.F.J. (1998) Antitumor polycyclic acridines. Part 3. A two-step conversion of 9-azidoacridine to 7H-pyrido[4,3,2-kl]acridines by Graebe-Ullmann thermolysis of 9-(1,2,3-triazol-1-yl)acridines. Journal of the Chemistry Society, Perkin Transactions 1, 915.
16. Herencia F., Ubeda A., Ferrandiz M.L., Terencio M.C., Alcaraz M.J., Garcia-Carrascosa M., Capaccioni R., Paya M. (1998) Anti-inflammatory activity in mice of extracts from Mediterranean marine invertebrates. Life Science, 62, 115.
17. Jimeno J.M., Faircloth G., Cameron L., Meely K., Vega E., Gomez A., Sousa-Faro J.M.F., Rinehart K. (1996) Progress in the acquisition of new marine-derived anticancer compounds: development of ecteinascidin-734 (ET-734). Drugs Future, 21, 1155.
18. Liu L.F. (1989) DNA topoisomerase poisons as antitumor drugs. Annual Review of Biochemistry, 58, 351.
19. Long B.H., Carboni J.M., Wasserman A.J., Cornell L.A., Casazza A.M., Jensen P.R., Lindel T., Fenical W., Fairchild C.R. (1998) Eleutherobin, a novel cytotoxic agent that induces tubulin polymerization, is similar to paclitaxel (taxol). Cancer Research, 58, 1111.
20. McDonald L.A., Eldredge G. S., Barrows L.R., Ireland C.M. (1994) Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. Journal of Medicinal Chemistry, 37, 3819.
21. McKee T.C., Bokesch H.R., McCormick J.L., Rashid J.H., Boyd M.R. (1997) Isolation and characterization of new anti-HIV and cytotoxic leads from plants, marine, and microbial organisms. Journal of Natural Products, 60, 431.
22. Mohammad R.M., Pettit G.R., Almatchy V.P., Wall N., Varterasian M., Al-Katib A. (1998) Synergistic interaction of selected marine animal anticancer drugs against human diffuse large cell lymphoma. Anti-Cancer Drugs, 9, 149.
23. Molinski T.F. (1993) Marine pyridoacridines: structure, synthesis, and biological chemistry. Chemical Reviews, 93, 1825.
24. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Campbell H., Mayo J., Boyd M. (1991) Feasibility of a high-flu anticancer drug screen using a diverse panel of cultured human tumor cell lines. Journal of the National Cancer Institute, 83, 757.
25. Norton R.S. (1998) Structure and function of peptide and protein toxins from marine organisms. Journal of Toxicology, Toxin Reviews, 17, 99.
26. Paull K.D., Shoemaker R.H., Monks A., Scudiero D.A., Rubinstein L., Plowman J., Boyd M.R. (1989) Journal of the National Cancer Institute, 81, 1088.
27. Plubrukarn A., Davidson B.S. (1998) Arnoamines A and B, new cytotoxic pentacyclic pyridoacridine alkaloids from the ascidian cystodytes sp. The Journal of Organic Chemistry, 63, 1657.
28. 13C coupling constants. Journal of the American Chemistry Society, 105, 4835.
29. Turner T., Jackson W.H., Pettit G. R., Wells A., Kraft A.S. (1998) Treatment of human prostate cancer cells with dolastatin 10, a peptide isolated from a marine shell-less mollusk. Prostate (N. Y.), 34, 175.
30. Wang H.Y., Al-Said N.H., Lown J.W. (1994) Convenient synthesis of pyrroloiminoquinone and its lextropsin-linked derivative. Tetrahedron Letters, 35, 4085.
31. Whitehouse M.W., Macrides T.A., Kalafatis N., Betts W.H., Haynes D.R., Broadbent J. (1997) Anti-inflammatory activity of a lipid fraction (lyprinol) from the NZ green-lipped mussel. Inflammopharmacology, 5, 237.
32. Zhao R.L., Lown J.W. (1997) A concise synthesis of the pyrroloquinoline nucleus of the makaluvamine alkaloids. Synthetic Communications, 27, 2103.
33. Zhao R.L., Oreski B., Lown J.W. (1996) Synthesis and biological evaluation of hybrid molecues containing the pyrroloquinoline nucleus and DNA-minor groove binders. Bioorganic and Medicinal Chemistry Letters, 6, 2169.