Dimeric naphthylisoquinoline alkaloids and synthesis methods the

Details Dimeric naphthylisoquinoline alkaloids and synthesis methods the Dimeric naphthylisoquinoline alkaloids and synthesis methods the

1996-07-01

1998-08-04

Davis, Zinna Northington

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546146, 546147, C07D40110

Patent

active

057895945

ABSTRACT:
The present invention provides methods of preparing dimeric naphthylisoquinoline alkaloids by coupling together two monomeric naphthylisoquinoline alkaloids, each of which may be the same or different, and one, both, or neither of which may possess a C-8' to C-5 naphthalene/isoquinoline linkage, to form homodimers or heterodimers, including the antiviral michellamines. The present invention also provides new, medically useful homodimeric and heterodimeric naphthylisoquinoline compounds and derivatives thereof.

REFERENCES:
patent: 5260315 (1993-11-01), Bringmann et al.
patent: 5409938 (1995-04-01), Boyd
Benfield et al., "Studies of Fungal and Plant Laccases," Phytochemistry, 3, 79-88 (1964).
Bobbitt, et al., "Electrochemistry of Natural Products. III. A Stereoselective, Stereospecific Phenol Coupling Reaction," J. Am. Chem. Soc., 93, 3551-3552 (1971).
Bringmann et al., "First total synthesis of korupensamines A and B," Heterocycles, 39(2), 503-508 (1994).
Boyd et al., "Anti-HIV Michellamines from Ancistrocladus korupensis," J. Medicinal Chemistry, 37(12), 1740-1745 (1994).
Bringmann, The Alkaloids, 29 (Brossi, ed.), Academic Press, New York, 1986, pp. 141-184.
Bringmann et al., "Isoquinolines and Naphthalenes from .beta.-Polyketones: Model Reactions for an Extraordinary Alkaloid Biosynsthesis," Angew. Chem. Int. Ed. Engl., 21(3), 200-201 (1982).
Bringmann et al., "Regioselective and Atropoisomeric-Selective Aryl Coupling to Give Naphthyl Isoquinoline Alkaloids: The First Total Synthesis of (-)-Ancistrocladine," Angew. Chem. Int. Ed. Engl., 25(10), 913-915 (1986).
Bringmann et al., "The Absolute Configuration of Michellamine B, A `Dimeric,` Anti-HIV-Active Naphthylisoquinoline Alkaloid," Angew. Chem. Int. Ed. Engl., 32(8), 1190-1191 (1993).
Bringmann et al., "Chiral Economy with Respect to Rotational Isomerism: Rational Synthesis of Hamatine and (Optionally) Ancistrocladine from Joint Helical Precursors," Heterocycles, 28(1), 137-142 (1989).
Bringmann, "Biomimetische Synthesen beider Molekulhalften der Ancistrocladus-und der Triphyophyllum-Alkaloide aus gemeinsamen Vorstufen," Liebigs Ann. Chem., 2126-2134 (1985).
Bringmann et al., "Atrop-diastereomer Separation by Racemate Resolution Techniques: N-Methyl-Dioncophylline A and its 7-Epimer from Ancistrocladus abbreviatus," Phytochemistry, 30(4), 1307-1310 (1991).
Bringmann et al., "Dioncopeltine A and Dioncolactone A: Alkaloids from Triphyophyllum peltatum," Phytochemistry, 30(5), 1691-1696 (1991).
Bringmann et al., "Dioncophylline B, A Naphtylisoquinoline Alkaloid with A New Coupling Type from Triphyophyllum peltatum," Phytochemistry, 30(11), 3845-3847 (1991).
Bringmann et al., "Ancistrobrevine B, The First Naphthylisoquinoline Alkaloid with a 5,8'-Coupling Site, and Related Compounds from Ancistrocladus abbreviatus," Phytochemistry, 31(11), 4011-4014 (1992).
Bringmann et al., "(.+-.)-Dioncophyllacine A, A Naphthylisoquinoline Alkaloid with a 4-Methoxy Substituent from the Leaves of Triphyophyllum peltatum," Phytochemistry, 31(11), 4015-4108 (1992).
Bringmann et al., "Dioncophylline C from the Roots of the Triphyophyllum peltatum, the First 5,1'-Coupled Dioncophyllaceae Alkaloid," Phytochemistry, 31(11), 4019-4024 (1992).
Bringmann et al., "On the Biosynthesis of Acetogenic Tetrahydroisoquinoline Alkaloids: First In Vivo Feeding Experiments," Planta Med., 57 (Suppl. 2), A98 (1991).
Bringmann et al., "Ancistrobrevine D: An Unusual Alkaloid from Ancistrocladus abbreviatus," Planta Med., 58 (Suppl. 1), A703-704 (1992).
Bringmann et al., "A New Atropisomeric Dioncophylline A Derivative from Triphyophyllum peltatum," Planta Med., 59 (Suppl.), A621-622 (1993).
Bringmann et al., "The Cultivation of Tropical Lianas of the Genus Ancistrocladus," Planta Med., 59 (Suppl.), A623-624 (1993).
Bringmann et al., "On the Structure of the Dioncophyllaceae Alkaloids Dioncophylline A (`Triphyophylline`) and `O-Methyl-Triphyophylline,`" Tetrahedron Letters, 31(5), 639-642 (1990).
Bringmann et al., "First Total Synthesis of (-)-Dioncophylline A (`Triphyophylline`) and of Selected Stereoisomers: Complete (Revised) Stereostructure," Tetrahedron Letters, 31(5), 643-646 (1990).
Bringmann et al., "Circular Dichroism of Michellamines: Independent Assignment of Axial Chirality by Calculated and Experimental CD Spectra," Tetrahedron, 50(26), 7807-7814 (1994).
Flaig et al., "Reaktionen Mit Oxydierenden Enzymen Aus Mikroorganismen," Planta Med., 9, 123-139 (1961).
Fleischhauer et al., "Messung und Berechnung der CD-Spektren der Biaryl-Alkaloide Ancistrocladein und Dioncophyllein A," Z. Naturforsch, 48b, 140-148 (1993).
Fran.cedilla.ois et al., "Activity of Extracts and Naphthylisoquinoline Alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and A. barteri against Plasmodium falciparum In Vitro," Phytochemistry, 35(6), 1461-1464 (1994).
Gulakowski et al., "A Semiautomated Multiparameter Approach for Anti-HIV Drug Screening," J. Virological Methods, 33, 87-100 (1991).
Harel et al., "Purification and Multiplicity of Catechol Oxidase from Apple Chloroplasts," Phytochemistry, 4, 783-790 (1965).
Holland, in Organic Synthesis with Oxidative Enzymes, Chapter 8, Miscellaneous Oxidative Bioconversions, "1. Oxidative Coupling of Phenols and the Formation of Quinones," VCH, Weinheim, 341-351, 380-381 (1992).
Laatsch, "Synthese von Biramentaceon, Mamegakinon und Rotundichinon," Liebigs Ann. Chem., 1321-1347 (1980).
Nicholl, in An Introduction to Genetic Engineering, Cambridge Univ. Press, Cambridge, pp. 1-5 & 127-130 (1994).
Old et al., in Principles of Gene Manipulation, Blackwell Scientific Publishers, London, pp. 3-13 & 108-221 (1992).
Robb et al., On the Heterogeneity of the Tyrosinase of Broad Bean (Vicia Faba L.), Pytochemistry, 4, 731-740 (1965).
Saunders, Peroxidase, Butterworth, London, pp. 1-52 (1964).
Scott, "Oxidative Coupling of Phenolic Compounds," in Quarterly Reviews (London), 19, 1-35 (1965).
Sofer, Introduction to Genetic Engineering, Butterworth-Heinemann, Stoneham, MA, pp. 1-21 & 103-126 (1991).
Steinberg et al., in Recombinant DNA Technology Concepts and Biomedical Applications, Prentice Hall, Englewood Cliffs, NJ, pp. 81-124 & 150-162 (1993).
Supko et al., "Determination of Michellamine B in Biological Fluids by High-Performance Liquid Chromatograph with Fluorescence Detection," Analytical Biochemistry, 216, 52-60 (1994).
Thomas et al., "Ancistrocladus korupensis (Ancistrocladaceae): A New Species of Liana from Cameroon," Novon, 3(4), 494-498 (1993).
Vlietstra et al, "Trimethylacetic Formic Anhydride. Improved Preparation and Use As a Highly Efficient and Selective N-formylating Reagent," J. Royal Netherlands Chemical Society, 101, 460-462 (1982).
Whiting, in Comprehnsive Organic Synthesis, (Trost and Fleming, eds.), Peragamon Press, Oxford, pp. 659-703 (1991).
Bringmann et al., "Biomimetic oxidative dimerization of korupensamine A: Completion of the first total synthesis of michellamines A, B, and C," Tetrahedron, 50(32), 9643-9648 (1994).
Hoye et al., "Total synthesis of michellamines A-C: Important anti-HIV agents," Tetrahedron Letters, 35(47), 8747-8750 (1994).
Kelly et al., "Convergent total synthesis of the michellamines," Tetrahedron Letters, 35(41), 7621-7624 (1994).
Manfredi et al., "Novel alkaloids from the tropical plant Ancistrocladus abbreviatus inhibit cell killing by HIV-1 and HIV-2," Journal of Medicinal Chemistry, 34(12), 3402-3405 (1991).

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