Lapachone compounds and methods of use thereof

Details Lapachone compounds and methods of use thereof Lapachone compounds and methods of use thereof

2011-03-08

2011-03-08

Solola, Taofiq A (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

Reexamination Certificate

active

07902354

ABSTRACT:
The present invention provides novel tricyclic spiro-oxathiine naphthoquinone derivatives, a synthetic method for making the derivatives, and the use of the derivatives to induce cell death and/or to inhibit proliferation of cancer or precancerous cells. The naphthoquinone derivatives of the present invention are related to the compound known as β-lapachone (3,4-dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione).

REFERENCES:
patent: 5763625 (1998-06-01), Boothman et al.
patent: 5824700 (1998-10-01), Frydman et al.
patent: 5969163 (1999-10-01), Frydman et al.
patent: 6245807 (2001-06-01), Pardee et al.
patent: 2002/0169135 (2002-11-01), Pardee et al.
patent: 2003/0091639 (2003-05-01), Jiang et al.
patent: 2004/0071775 (2004-04-01), Jiang et al.
patent: 2004/0266857 (2004-12-01), Jiang et al.
patent: WO 94/04145 (1994-03-01), None
patent: WO 99/47497 (1999-09-01), None
patent: WO 00/61142 (2000-10-01), None
patent: WO 03/011224 (2003-02-01), None
patent: WO 2004/045557 (2004-06-01), None
Abell et al., “The Wittig and related reactions”, inOrganophosphorus Reagents, Chapter 4, pp. 99-127, Oxford University Press, Inc., New York (2004).
Adcock et al., “Substituent Effects. VIII. Synthesis of Substituted α- and β-Fluoronaphthalenes”,J. Am. Chem. Soc., 89(2):386-390 (1967).
Brittain et al., “Triphenylsilanethiol: A Solid H2S Equivalent in the Ring Openings of Epoxides”,Tetra. Let., 34(21):3363-3366 (1993).
Chuang et al., “Oxidative Free Radical Reaction of 2-Phenylthio-1,4-Naphthoquinones Initiated by Manganese(III) Acetate”,Heterocycles, 43(10):2215-2221 (1996).
Cordero-Vargas et al., “Synthesis of substituted naphthalenes from α-tetralones generated by a xanthate radical addition-cyclisation sequence”,Org. Biomol. Chem., 2:3018-3025 (2004).
Edmonds et al., “The Wittig Reaction”, inModern Carbonyl Olefination, Chapter 1, pp. 1-17, Verlag GmbH & co. KGaA, Weinheim (2004).
Goncalves et al., “Evaluation of the Toxicity of 3-Allyl-β-Lapchone Against Trypa-Nosoma Cruzi Bloodstream Forms”,Mol. Biochem. Parasit., 1:167-176 (1980).
Hale et al., “1,3,4-Trisubstituted Pyrrolidine CCR5 Receptor Antagonists. Part 3: Polar Functionality and Its Effect on Anti-HIV-1 Activity”,Bioorg. Med. Chem. Lett., 12(20):2997-3000 (2002).
Huang et al., “β-Lapacone Induces Cell Cycle Arrest and Apoptosis in Human Colon Cancer Cells”,Mol. Med., 5:711-720 (1999).
Jambulingam et al., “Synthetic, Structural and Antimicrobial Studies of Some Substituted 2,6-dipehnyl-1-aza-7-oxa-4-spiro[2,5]octanes”,Asian J. Chem., 16(3-4):1261-1268 (2004).
Klapars et al., “Copper-Catalyzed Halogen Exchanged in Aryl Halides: An Aromatic Finkelstein Reaction”,J. Am. Chem. Soc., 124:14844-14845 (2002).
Krapcho et al., “Heterosubstituted Anthracene-9,10-dione Analogues. The Synthesis and Antitumor Evaluation of 5,8-Bis[(aminoalkyl)amino]naphtha[2,3-b]thiophen-4,9-diones”,J. Med. Chem., 33(9):2651-2655 (1990).
Krohn et al., “Transition Metal Catalyzed Oxidations; 4. Improved Method for the Oxidation of 1- and 2-Naphthols to 1,2-Napthoquinones”,Synthesis, 12:1141-1143 (1990).
Kurokawa, S., “The reaction of Cadalene and Eudalen with Sulfur”,Bul. Chem. Soc. Jap., 43(5):1454-1459 (1970).
Lai et al., “β-lapachone induced cell death in human hepatoma (HepA2) cells”,Histol. Histopathol., 13:89-97 (1998).
Lawrence, N.J., “The Wittig reaction and related methods”, inPreparation of Alkenes, Chapter 2, pp. 19-58 (1996).
Li et al., “β-Lapachone, a Novel DNA Topoisomerase I Inhibitor with a Mode of Action Different from Camptothecin”,J. Biol. Chem., 268(30):22463-22468 (1993).
Li et al., “Induction of Apoptosis by β-Lapachone in Human Prostate Cancer Cells”,Cancer Res., 55:3712-3715 (1995).
Li et al., “Potent Induction of Apoptosis by β-Lapachone in Human Multiple Myeloma Cell Lines and Patient Cells”,Mol. Med., 6(12):1008-1015 (2000).
Li et al., “Potent inhibition of tumor survival in vivo by β-lapachone plus taxol: Combining drugs imposes different artifical checkpoints”,PNAS, 96(23):13369-13374 (1999).
Li et al., “Release of Mitochondiral Cytochrome C in Both Apoptosis and Necrosis Induced by β-Lapachone in Human Carcinoma Cells”,Mol. Med., 5:232-239 (1999).
Li et al., “Selective killing of cancer cells by β-lapachone: Direct checkpoint of activation as a strategy against cancer”,PNAS, 100(5):2674-2678 (2003).
Paquet et al., “Reactions of polar dienes witho-quinones”,Can. J. Chem., 67(8):1354-1358 (1989).
Perumal et al., “Oxidation of Halophenols and Highly Substituted Phenols with Lead(IV)Acetate”,Synthesis, 11:943-945 (1980).
Planchon et al., “β-Lapachone-mediated Apoptosis in Human Promyelocytic Leukemia (HL-60) and Human Prostate Cancer Cells: A p53-independent Response”,Cancer Res., 55:3706-3711 (1996).
Portela et al., “Redox Cycling of β-Lapchone and Relatedo-Naphthoquinones in the Presence of Dihydrolipoamide and Oxygen”,Biochem. Pharm., 51:275-283 (1996).
Prieto et al., “Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection”,JOC, 69(20):6812-6820 (2004).
Schaffner-Sabba et al., “β-Lapachone: Synthesis of Derivatives and Activities in Tumor Models”,J. Med. Chem., 27:990-994 (1984).
Schaus et al., “Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)CoIIIComplexes. Practical Syntheis of Enantioenriched Terminal Epoxides and 1,2-Diols”,J. Am. Chem. Soc., 124(7):1307-1315 (2002).
Steffan et al., “Novel Substituted 4-Aminomethylpiperidines as Potent and Selective Human β3-Agonists. Part1: Aryloxypropanolaminomethylpiperidines”,Bioorg. Med. Chem. Lett., 12:2957-2961 (2002).
Suginome et al., “One-step Synthesis of 2,3-Dihydronaphtho[2,3-b]thiophene-4,9-diones by a New Regioselective [3+2] Photoaddition of Photogenerated 2-Mercapto-1,4-naphthoquinone with Alkenes”,J. Chem. Soc., Chem. Commun., 9:807-809 (1993).
Tapia et al., “Synthesis of 2H-Naphtho[2,3-b]Thiopyranoquinones and Density Functional Study for the Diels-Alder Reaction of a Benzothiopyranoquinone”,Heterocycles, 53(3):585-598 (2000).
Tapia et al., “Synthesis of 3,4-Dihydro-4-hydroxy-9-methoxy-2H-naphtho[2,3-b]thiopyranoquinone”,Tetrahedron Letters, 38(1):153-154 (1997).
Tonholo et al., “Electrochemical Properties of Biologically Active Heterocyclic Naphthoquinones”,J. Braz. Chem. Soc., 9(2):163-169 (1988).
Weller et al., “Topoisomerase-I Inhibitors for Human Malignant Glioma: Differential Modulation of p53, p21, bax and bcl-2 Expression and of CD95-Mediated Apoptosis by Camptothecin and β-Lapachone”,Int. J. Cancer, 73:707-714 (1997).
Wuertzberger et al., “Induction of Apoptosis in MCF-7:WS8 Breast Cancer Cells by β-Lapachone”,Cancer Res., 58:1876-1885 (1998).

Affiliated with

Also associated with

Rating

Lapachone compounds and methods of use thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Lapachone compounds and methods of use thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Lapachone compounds and methods of use thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2625206