Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-01-04
1997-04-22
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514183, 540145, 540472, 540474, 540465, 536 187, C07D48722, A61K 31395
Patent
active
056229453
ABSTRACT:
The present invention is directed to the synthesis and use of novel macrocyclic compounds, based upon a new class of expanded porphyrins, termed rubyrins. Disclosed herein is the structure and synthesis of a prototypical rubyrin and various substituted rubyrin analogues, conjugates and compositions. Rubyrin itself is characterized by the presence of six pyrrolic subunits contained within a fully aromatic 26 .pi.-electron macrocyclic framework and by UV/VIS absorption bands that are very red-shifted as compared to those of other porphyrins or pentapyrrolic expanded porphyrins. The rubyrin-type class of compounds is further characterized by an ability to undergo facile protonation at the pyrrolic nitrogens and, once protonated, by an ability to form complexes with anions such as nucleotide-containing compounds. Rubyrin-based compounds are useful as, for example, anion chelators and receptors and as transporters for various anionic compounds including antiviral agents. In addition to the 26 .pi.-electron target system, the present invention concerns other oxidation states bearing the same connectivity and the same total number of non-hydrogen atoms, and various analogues in which different substituents are present at the various meso and/or .beta.-pyrrolic positions or in which furan and/or thiophene moieties replace one or more of the six pyrrolic subunits.
REFERENCES:
patent: 4833790 (1989-05-01), Levy et al.
patent: 4935498 (1990-06-01), Sessler et al.
patent: 5041078 (1991-08-01), Matthews et al.
patent: 5410045 (1995-04-01), Sessler
Kus et al., Tetrahedron letters, vol. 31 No. 36 pp. 5133-5134, 1990.
Aoyama et al., "Multi-Point Interaction of Phosphates with Protonated Pyridylporphyrin. Discrimination of Monoalkyl and Dialkyl Phosphates," Chemistry Letters, 1241-1244, 1991.
Bauer et al., "Sapphyrins: Novel Aromatic Pentapyrrolic Macrocycles," J. Am. Chem. Soc., 105:6429-6436, 1983.
Broadhurst and Grigg, "18- and 22-.pi.-Electron Macrocycles Containing Furan, Pyrrole, and Thiophen," Chemical Communications, 1480-1482, 1969.
Broadhurst and Grigg, "The Synthesis of 22 .pi.-Electron Macrocyles. Sapphyrins and Related Compounds," JCS Perkin, 2111-2116, 1972.
Claude et al., "Binding of Nucleosides, Nucleotides, and Anionic Planar Substrates by Bis-Intercaland Receptor Molecules," J. Chem. Soc., Chem. Commun., 17:1182-1185, 1991.
Cramer et al., "Synthesis and Structure of the Chloride and Nitrate Inclusion Complexes of [16-Pyrimidinium crown-4]," J. Am. Chem. Soc., 113:7033-7034, 1991.
Cuellar and Marks, "Synthesis and Characterization of Metallo and Metal-Free Octaalkylphthalocyanines and Uranyl Decaalkylsuperphthalocyanines," Inorg. Chem., 20:3766-3770, 1981.
Dietrich et al., "Proton Coupled Membrane Transport of Anions Mediated by Cryptate Carriers," J. Chem. Soc. Chem. Comm., 11:691-692, 1988.
Dixon et al., "Molecular Recognition: Bis-Acylguanidiniums Provide a Simple Family of Receptors for Phosphodiesters," J. Am. Chem. Soc., 114:365-366, 1992.
Furuta et al., "Phosphate Anion Binding: Enhanced Transport of Nucleotide Monophosphates Using a Sapphyrin Carrier," J. Am. Chem. Soc., 113:6677-6678, 1991.
Furuta et al., "Enhanced Transport of Nucleosides and Nucleoside Analogues with Complementary Base-Pairing Agents," J. Am. Chem. Soc., 113: 4706-4707, 1991.
Furuta et al., "Protonated Rubyrin and C-Tips: Co-carriers for the Transport of Guanosine 5'-Monophosphate at Neutral pH," Supramolec. Chem., 1-9 (1991).
Galan et al., "A Synthetic Receptor for Dinucleotides," J. Am. Chem. Soc., 113:9424-9425, 1991.
Galan et al., "Selective Complexation of Adenosine Monophosphate Nucleotides by Rigid Bicyclic Guanidinium Abiotic Receptors," Tetrahedron Letters, 32(15):1827-1830, 1991.
Harriman et al., "Metallotexaphyrins: A New Family of Photosensitisers for Efficient Generation of Singlet Oxygen," J. Chem. Soc. Chem. Comm., 314-316, 1989.
Hisatome et al., "Porphyrins Coupled with Nucleoside Bases. Synthesis and Characterization of Adenine- and Thymine-Porphyrin Derivatives," Chem. Lett., 2251-2254, 1990.
Hosseini et al., "Multiple Molecular Recognition and Catalysis. A Multifunctional Anion Receptor Bearing an Anion Binding Site, an Intercalating Group, and a Catalytic Site for Nucleotide Binding and Hydrolysis," J. Am. Chem. Soc., 112:3896-3904, 1990.
Hosseini et al., "Multiple Molecular Recognition and Catalysis. Nucleotide Binding and ATP Hydrolysis by a Receptor Molecule Bearing an Anion Binding Site, an Intercalator Group and a Catalytic Site," J. Chem. Soc. Chem. Comm., 9:596-598, 1988.
Kimura et al., "A Study of New Bis(macrocylic polyamine) Ligands as Inorganic and Organic Anion Receptors," J. Org. Chem., 55(1):46-48, 1990.
Kimura, "Macrocyclic Polyamines as Biological Cation and Anion Complexones--An Application to Calculi Dissolution," 113-141 (1990).
Kral et al., "Synthetic Sapphyrin-Cytosine Conjugates: Carriers for Selective Nucleotide Transport at Neutral pH," J. Am. Chem. Soc., 114:8704-8705, 1992.
Li and Diederich, "Carriers for Liquid Membrane Transport of Nucleotide 5'-Triphosphates," J. Org. Chem., 47:3449-3454, 1992.
Marks and Stojakowvic, "Large Metal Ion-Centered Template Reactions. Chemical and Spectral Studies of the `Superphthalocyanine` Dioxocyclopentakis (1-iminoisoindolinato)uranium(VI) and Its Derivatives," J. Am. Chem. Soc., 1695-1705, 1978.
Rexhausen and Gossauer, "The Synthesis of a New 22 .pi.-Electron Macrocycle: Pentaphyrin," Chem. Soc. Chem. Comm., 6:275, 1983.
Schmidtchen, "A Non-Macrocyclic Host for Binding Organic Phosphates in Protic Solvents," Tetrahedron Letters, 30(34):4493-4496, 1989.
Seel and Vogtle, "Molecular Recognition and Transport of Nucleobases--Superiority of Macrobicyclid Host Molecules," Angew Chem. Int. Ed. Engl., 30(4):442-444, 1991.
Sessler et al., "Anion Binding: A New Direction in Porphyrin-Related Research," Pure & Appl. Chem., 65(3):393-398, 1993.
Sessler et al., "Rubyrin: A New Hexapyrrolic Expanded Porphyrin," Angew. Chem. Int. Ed., Engl., 1991.
Sessler et al., "Cytosine Amine Derivatives," J. Org. Chem., 47:826-834, 1992.
Sessler et al., "Enhanced Transport of Fluoride Anion Effected Using Protonated Sapphyrin as a Carrier," J. Chem. Soc. Chem. Comm., 1732-1735, 1991.
Sessler et al., "In vitro photodynamic activity of diprotonated sapphyrin: a 22-.pi.-electron pentapyrrolic prophyrin-like macrocycle," Chem. Abstr., 112:348-349, 112:194584t, 1990.
Sessler et al., "A water-stable gadolinium (III) complex derived from a new pentadentate expanded porphyrin ligand," Chem. Abstr., 111:720, 111:125716e, 1989.
Sessler et al., "Synthetic and Structural Studies of Sapphyrin, a 22-.pi.-Electron Pentapyrrolic `Expanded Porphyrin`, " J. Am. Chem. Soc., 112:2810-2813, 1990.
Sessler et al., "An `Expanded Porphyrin`: The Synthesis and Structure of a New Aromatic Pentadentate Ligand," J. Am. Chem. Soc., 110:5586-5588, 1988.
Sessler and Burrell, "Expanded Porphyrins," Current Chem., 161:66-71 (1990).
Shionoya et al., "Diprotonated Sapphyrin: A Fluoride Selective Halide Anion Receptor," J. Am. Chem. Soc., 114:5714-5722, 1992.
Tabushi et al., "Lipophilic Diammonium Cation Having a Rigid Structure Complementary to Pyrophosphate Dianions of Nucleotides. Selective Extraction and Transport of Nucleotides," J. Am. Chem. Soc., 103:6152-6157, 1981.
Tohda et al., "Liquid Membrane Electrode for Guanosine Nucleotides Using a Cytosine-Pendant Triamine Host as the Sensory Element," Analyt. Chem., 64(8):960-964, 1992.
Iverson et al., "Phosphate Recognition by Sapphyrin. A New Approach to DNA Binding," J. Am. Chem. Soc., 115:11022-11023, 1993.
Sessler et al., "Phosphate Anion Chelation and Base-pairing. Design of Receptors and Carriers for Nucleotides and Nucleotide Analogs," Supramolec. Chem., 1:209-220, 1993.
Sessler et al., "Expanded Porphyrins. Receptors for Cationic, Anionic, and Neutral Substrates," in Transition Metals in Supramolecular Chemistry, NATO ASI Series; Fabbrizzi, L. and Poggi, A., Eds., Kluwer, Dorderecht, Series C, 448:391-408, 1994.
Gossauer et al., Bull. Soc. Chem. Belg., 92:793-795, Sep. 1983.
Morishima Takashi
Sessler Jonathan L.
Weghorn Steven J.
Board of Regents , The University of Texas System
Shah Mukund J.
Sripada Pavanaram K.
LandOfFree
Rubyrin macrocycles does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Rubyrin macrocycles, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Rubyrin macrocycles will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-341652