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Collect. Czech. Chem. Commun. 1995, 60, 1196-1212

Synthesis of Enantiomeric N-(2-Phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine Bases. I. The Stepwise Approach

Antonín Holý and Milena Masojídková

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic

Crossref Cited-by Linking

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  • Li Man, Zhou Ting, Zhang Qing-Wen: Chiral Analysis of the Key Intermediates of Tenofovir Alafenamide Fumarate. Pharmaceutical Fronts 2023, 05, e38. <>
  • Baszczyňski Ondřej, Kaiser Martin Maxmilian, Česnek Michal, Břehová Petra, Jansa Petr, Procházková Eliška, Dračínský Martin, Snoeck Robert, Andrei Graciela, Janeba Zlatko: Xanthine-based acyclic nucleoside phosphonates with potent antiviral activity against varicella-zoster virus and human cytomegalovirus. Antivir Chem Chemother 2018, 26, 204020661881305. <>
  • Blindauer Claudia A., Sigel Astrid, Operschall Bert P., Griesser Rolf, Holý Antonín, Sigel Helmut: Extent of intramolecular π stacks in aqueous solution in mixed-ligand copper(II) complexes formed by heteroaromatic amines and the anticancer and antivirally active 9-[2-(phosphonomethoxy)ethyl]guanine (PMEG). A comparison with related acyclic nucleotide analogues. Polyhedron 2016, 103, 248. <>
  • Rivera Nelo R., Moore Jeffrey, Schenk David J., Wang Heather, Hesk David, Mergelsberg Ingrid: Enzymatic approach toward the synthesis of isotopically labeled ( R )-9-(2-hydroxypropyl)adenine. Tetrahedron Letters 2016, 57, 1090. <>
  • Ocampo Charles E., Lee Doris, Jamison Timothy F.: Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir. Org. Lett. 2015, 17, 820. <>
  • Zhang Qian, Ma Bai-Wei, Wang Qian-Qian, Wang Xing-Xing, Hu Xia, Xie Ming-Sheng, Qu Gui-Rong, Guo Hai-Ming: The Synthesis of Tenofovir and Its Analogues via Asymmetric Transfer Hydrogenation. Org. Lett. 2014, 16, 2014. <>
  • Krečmerová Marcela, Jansa Petr, Dračínský Martin, Sázelová Petra, Kašička Václav, Neyts Johan, Auwerx Joeri, Kiss Eleonóra, Goris Nesya, Stepan George, Janeba Zlatko: 9-[2-(R)-(Phosphonomethoxy)propyl]-2,6-diaminopurine (R)-PMPDAP and its prodrugs: Optimized preparation, including identification of by-products formed, and antiviral evaluation in vitro. Bioorganic & Medicinal Chemistry 2013, 21, 1199. <>
  • Jansa Petr, Baszczyňski Ondřej, Procházková Eliška, Dračínský Martin, Janeba Zlatko: Microwave-assisted hydrolysis of phosphonate diesters: an efficient protocol for the preparation of phosphonic acids. Green Chem. 2012, 14, 2282. <>
  • Pinheiro Eloan dos Santos, Antunes Octavio Augusto Ceva, Fortunak Joseph M.D.: A survey of the syntheses of active pharmaceutical ingredients for antiretroviral drug combinations critical to access in emerging nations. Antiviral Research 2008, 79, 143. <>
  • Holý Antonin: Synthesis of Acyclic Nucleoside Phosphonates. CP Nucleic Acid Chemistry 2005, 22. <>
  • Clercq Erik De, Holý Antonín: Acyclic nucleoside phosphonates: a key class of antiviral drugs. Nat Rev Drug Discov 2005, 4, 928. <>
  • Braun Manfred, Hohmann Andreas, Rahematpura Jaykumar, Bühne Corinna, Grimme Stefan: Synthesis and Determination of the Absolute Configuration of Fugomycin and Desoxyfugomycin: CD Spectroscopy and Fungicidal Activity of Butenolides. Chemistry A European J 2004, 10, 4584. <>
  • Laux Wolfgang H.G., Pande Praveen, Shoshani Ilana, Gao Junyuan, Boudou-Vivet Valérie, Gosselin Gilles, Johnson Roger A.: Pro-nucleotide Inhibitors of Adenylyl Cyclases in Intact Cells. Journal of Biological Chemistry 2004, 279, 13317. <>
  • Birkuš Gabriel, Hájek Miroslav, Kramata Pavel, Votruba Ivan, Holý Antonín, Otová Berta: Tenofovir Diphosphate Is a Poor Substrate and a Weak Inhibitor of Rat DNA Polymerases α, δ, and ε*. Antimicrob Agents Chemother 2002, 46, 1610. <>
  • Zı́dek Zdenĕk, Franková Daniela, Holý Antonı́n: Activation by 9-( R )-[2-(Phosphonomethoxy)Propyl]Adenine of Chemokine (RANTES, Macrophage Inflammatory Protein 1α) and Cytokine (Tumor Necrosis Factor Alpha, Interleukin-10 [IL-10], IL-1β) Production. Antimicrob Agents Chemother 2001, 45, 3381. <>
  • Holý Antonín, Votruba Ivan, Tloušťová Eva, Masojídková Milena: Synthesis and Cytostatic Activity of N-[2-(Phosphonomethoxy)alkyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds. Collect. Czech. Chem. Commun. 2001, 66, 1545. <>
  • Zı́dek Z, Franková D, Holý A: Macrophage activation by antiviral acyclic nucleoside phosphonates in dependence on priming immune stimuli. International Journal of Immunopharmacology 2000, 22, 1121. <>
  • Prota Andrea, Vogt Joachim, Pilger Beatrice, Perozzo Remo, Wurth Christine, Marquez Victor E., Russ Pamela, Schulz Georg E., Folkers Gerd, Scapozza Leonardo: Kinetics and Crystal Structure of the Wild-Type and the Engineered Y101F Mutant of Herpes simplex Virus Type 1 Thymidine Kinase Interacting with (North)-methanocarba-thymidine,. Biochemistry 2000, 39, 9597. <>
  • Bacchelli Corinne, Condom Roger, Patino Nadia, Aubertin Anne-Marie: Synthesis and Biological Activities of New Carbaacyclonucleosides and 1′-Oxaacyclonucleosides Related to Clitocine. Nucleosides, Nucleotides and Nucleic Acids 2000, 19, 567. <>
  • Schultze Lisa M., Chapman Harlan H., Dubree Nathan J.P., Jones Robert J., Kent Kenneth M., Lee Thomas T., Louie Michael S., Postich Michael J., Prisbe Ernest J., Rohloff John C., Yu Richard H.: Practical synthesis of the anti-HIV drug, PMPA. Tetrahedron Letters 1998, 39, 1853. <>
  • Zı́dek Zdeněk, Holý Antonı́n, Franková Daniela: Antiretroviral agent (R)-9-(2-phosphonomethoxypropyl)adenine stimulates cytokine and nitric oxide production. European Journal of Pharmacology 1997, 331, 245. <>
  • Zidek Zdeněk, Holy Antonin, FrankovÁ Daniela: Immunomodulatory properties of antiviral acyclic nucleotide analogues: Cytokine stimulatory and nitric oxide costimulatory effects. International Journal of Immunopharmacology 1997, 19, 587. <>
  • HOLY A., MASOJIDKOVA M.: ChemInform Abstract: Synthesis of Enantiomeric N‐(2‐Phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine Bases. Part 1. The Stepwise Approach. ChemInform 1996, 27. <>
  • Larrow Jay F., Schaus Scott E., Jacobsen Eric N.: Kinetic Resolution of Terminal Epoxides via Highly Regioselective and Enantioselective Ring Opening with TMSN3. An Efficient, Catalytic Route to 1,2-Amino Alcohols. J. Am. Chem. Soc. 1996, 118, 7420. <>