Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1999-02-01
2000-05-30
Lee, Howard C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
514691, C07C 49105
Patent
active
060692839
ABSTRACT:
The present invention provides illudin analogs of the general formula (I): ##STR1## where R.sub.1 is (CH.sub.2).sub.n --X--Y or H; n is 0 to 4; X is O or S or N or absent; and Y is an optionally substituted (C.sub.1 -C.sub.8)alkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.4)alkyl or cyclo(C.sub.3 -C.sub.6)alkyl optionally comprising one or more heteroatoms; a monosaccharide, an amino acid residue, or H when n is 2-4;
REFERENCES:
patent: 5387578 (1995-02-01), Angelucci et al.
patent: 5439936 (1995-08-01), Kelner et al.
patent: 5439942 (1995-08-01), Kelner et al.
patent: 5523490 (1996-06-01), Kelner et al.
patent: 5563176 (1996-10-01), Kelner et al.
Anchel, M., et al., "Antibiotic Substances From Basidiomycetes. VII. Clitocybe Illudens", Proceedings of the National Academy of Sciences of the United States of America, 36, 300-305, (May 1950).
Anchel, M., et al., "The Biogenesis of Illudins S and M in Clitocybe Illudens", Phytochemistry, 9, 2339-2343, (1970).
Brandsteterova, E., et al., "HPLC Analysis of Novel Anti-Cancer Agents-Illudens and Their Analogs", J. Liquid Chromatography, 16 (1), 115-125, (1993).
Brandsteterova, E., et al., "HPLC Determination of a New Anticancer Agent (Acylfulvene) in Serum", Neoplasma, 39 (6), 369-373, (1992).
Burres, N.S., et al., "Antitumor Activity and Mechanism of Action of the Novel Marine Natural Products Mycalamide-A and -B and Onnamide", Cancer Research, 49, 2935-2940, (Jun., 1989).
Curtis, E.A., et al., "An Efficient Dipolar-Cycloaddition Route to the Pterosin Family of Sesquiterpenes", Tetrahedron Letters, vol. 36, No. 12, pp. 1989-1992, (1995).
Dillman, R.O., et al., "Athymic Mouse Model of a Human T-Cell Tumor", Cancer Research, 45, 5632-5636, (Nov., 1985).
Eva, K.M., et al., "An Efficient Sythesis of Pterosin C and Other Pterosins", Can. J. Chem, 62, 1945-1953, (1984).
Giovanella, B.C., et al., "Correlation Between Response to Chemotherapy of Human Tumors in Patients and in Nude Mice", Cancer, 52, 1146-1152, (1983).
Giovanella, B.C., et al., "DNA Topoisomerase I-Targeted Chemotherapy of Human Colon Cancer in Xenografts", Science, 246, 1046-1048, (Nov., 1989).
Goldin, A., et al., "Current Results of the Screening Program at the Division of Cancer treatment, National Cancer Institute", Europ. J. Cancer, 17, 129-142, (1981).
Goldin, A., et al., "Historical Development and Current Strategy of the National Cancer Institute Drug Development Program", In: Methods in Cancer Research, vol. XVI, Academic Press, Inc., 165-245, (1979).
Hanson, J.R., et al., "Studies in Terpenoid Biosynthesis. Part XV. Biosynthesis of the Sesquiterpenoid Illuden M", J.C.S. Perkins I, 876-880, (1976).
Hara, M., et al., "6-Deoxyilludin M, a New Antitumor Antibiotic: Fermentation, Isolation and Structural Identification", The Journal of Antibiotics, 40, 1643-1646, (Nov., 1987).
Harttig, U., et al., "Leaianafulvene, a Sesquiterpenoid Fulvene Derivative from Cultures of Mycena Leaiana", Phytochemistry, 29 (12), 3942-3944, (1990).
Hirono, I., et al., "Repreoduction of Acute Bracken Poisoning in a Calf with Ptaquiloside, a Bracken Constituent", The Veterinary Record, 115, Abstract No. 85067284, STN File Server, File Medline, 375-378, (Oct., 1984).
Inoue, K., et al., "Antitumor Efficacy of Seventeen Anticancer Drugs in Human Breast Cancer Xenograft (MX-1) Transplanted in Nude Mice", Cancer Chemother. Pharamacol., 10, 182-186, (1983).
Kawato, Y., et al., "Antitumor Activity of a Camptothecin Derivative, CPT-11, Against Human Tumor Xenografts in Nude Mice", Cancer Chemother. Pharmacol., 28, 192-198, (1991).
Kelner, M.J., et al., "In Vitro and In Vivo Studies on the Anticancer Activity of Dehydroilluden M", Anticancer Research, 15, 873-878, (1995).
Kelner, M.J., et al., "Nonresponsiveness of the Metastatic Human Lung Carcinoma MV522 Xenograft to Conventional Anticancer Agents", Anticancer Research, 15, 867-872, (1995).
Kelner, M.J., et al., "Preclinical Evaluation of Illudens as Anticancer Agents", Cancer Research, 47, 3186-3189, (1987).
Kelner, M.J., et al., "Preclinical Evaluation of Illudens as Anticancer Agents: Basis for Selective Cytotoxicity", J. Natl. Cancer Inst., 82 (19), 1562-1565, (1987).
Matsumoto, T., et al., "An Alternative Synthesis of Illudin M", Tetrahedron Letters, 14, 1171-1174, (1970).
Matsumoto, T., et al., "Synthesis of Illudin S", Tetrahedron Letters, 23, 2049-2052, (1971).
McMorris, T.C., et al., "(Hydroxymethyl) Acyfulvene: An Illuden Derivative with Superior Antitumor Properties", J. Nat. Prod., 59, 896-899, (1996).
McMorris, T.C., et al., "Acylfulvenes, a New Class of Potent Antitumor Agents", Experientia, vol. 52(1), pp. 75-80, (Apr. 21, 1995).
McMorris, T.C., et al., "An Acetal Derivative of Illudin S with Improved Antitumor Activity", Tetrahedron letters, vol. 38, No. 10, pp. 1697-1698, (1997).
McMorris, T.C., et al., "Design and Synthesis of Antitumor Acylfulvenes", J. Org. Chem, vol. 62,, pp. 3015-3018, (1997).
McMorris, T.C., et al., "Fungal Metabolites. The Structures of the Novel Sesquiterpenoids Illudin -S and -M", J. of Amer. Chem. Soc., 87 (7), 1594-1600, (1965).
McMorris, T.C., et al., "On the Mechanism of Toxicity of Illudens: The Role of Gluthathione", Chem. Res. Toxicol., 3, 574-579, (1990).
McMorris, T.C., et al., "Reaction of Antitumor Hydroxymethylacylfulvene (HMAF) with Thiols", Tetrahedron, 53 (43), 14579-14590, (1997).
McMorris, T.C., et al., "Structure and reactivity of Illudens", Tetrahedron, 45 (17), 5433-5440, (1989).
McMorris, T.C., et al., "Structure-Activity Relationships of Illudens: Analogs with Improved Therapeutic Index", J. Org. Chem., 57, 6876-6883, (1992).
McMorris, T.C., et al., "Total Synthesis of hydroxymethylacylfulvene, an antitumour derivative of illudin S", Chem. Commun., pp. 315-316, (1997).
Padwa, A., et al., "An approach toward the Illudin family of sesquiterpenes using the tandem cyclization-cycloaddition reaction of rhodium carbenoids", J. Org. Chem, vol. 62, pp. 1317-1325, (1997).
Padwa, A., et al., "Generation and Cycloaddition behavior of spirocyclic carbonly ylides. Application to the synthesis of the Pterosin Family of Sequiterpenes", J. Org. Chem., vol. 61, pp. 73-81, (1996).
Padwa, A., et al., "Synthetic studies toward Illudins and Ptaguilosin. A Highly Convergent approach via the dipolar cycloaddition of carbonyl ylides", J. Am. Chem. Soc., Vo. 116, pp. 2667-2668, (1994).
Schabel, F.M., et al., "Testing Therapeutic Hypotheses in Mice and Man:Observations on the Therapeutic Activity Against Advanced Solid Tumors of Mice Treated with Anticancer Drugs that Have Demonstrated or Potential Clinical Utility for Treatment of Advanced Solid Tumors of Man", In: Methods in Cancer Research, vol. XVII, Academic Press, Inc., pp. 3-50, (1979).
Shinozawa, S., et al., "The Antitumor Effect of Illudin S (Lampterol) Entrapped in Liposome for Mice Inolculated with Ehrlich Ascites Tumor Cells", Abstract No. 197682, STN File Server CAS Chemical Abstracts, 90, (1979).
Steel, G.G., et al., "The Response to Chemotherapy of a Variety of Human Tumor Xenografts", Br. J. Cancer, 47, 001-013, (1983).
Tanaka, K., et al., "Metabolism by Rat Liver Cytosol of Illuden S, a Toxic Substance of Lampteromyces Japonicus. II. Characterization of Illuden S-Metabolizing Enzyme", Xenobiotica, 22 (1),, 33-39, (1992).
Tanaka, K., et al., "Metabolism of Illuden S, a Toxic Principle of Lampteromyces Japonicus, by Rat Liver. I. Isolation and Identification of Cyclopropane Ring-Cleavage Metabolites", Xenobiotica, 20 (7), 671-681, (1990).
Tanaka, K., et al., "Michael-type addition of illudin S, a toxic substance from Lampteromyces japonicus with Cysteine and Cysteine-containing peptides in vitro", Chem. Pharm. Bull., vol. 44, No. 2, 273-279, (1996).
Varki, N.M., et al., "Cloned Low Metastic Variants from Human Lung Carcinoma Metastases", Anticancer Research, 10, 637-644, (1990).
Vendetti, J.M., et al., "Current NCI Preclinical Antitumor Screening in Vivo: Results of Tumor Panel Screening, 1976-1982, and Future Directions", Advances in Pharmacology and Chemotherapy, 20, 1-20, (1984).
Venditti, J.M., "The National Cancer Inst
Kelner Michael J.
McMorris Trevor C.
Lee Howard C.
The Regents of the University of California
LandOfFree
Illudin analogs useful as antitumor agents does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Illudin analogs useful as antitumor agents, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Illudin analogs useful as antitumor agents will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1911466