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Collect. Czech. Chem. Commun. 1989, 54, 2190-2210
https://doi.org/10.1135/cccc19892190

Synthesis of N-(2-phosphonylmethoxyethyl) derivatives of heterocyclic bases

Antonín Holý, Ivan Rosenberg and Hana Dvořáková

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6

Crossref Cited-by Linking

  • Krečmerová Marcela, Majer Pavel, Rais Rana, Slusher Barbara S.: Phosphonates and Phosphonate Prodrugs in Medicinal Chemistry: Past Successes and Future Prospects. Front. Chem. 2022, 10. <https://doi.org/10.3389/fchem.2022.889737>
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  • Ban Željka, Žinić Biserka, Vianello Robert, Schmuck Carsten, Piantanida Ivo: Nucleobase–Guanidiniocarbonyl-Pyrrole Conjugates as Novel Fluorimetric Sensors for Single Stranded RNA. Molecules 2017, 22, 2213. <https://doi.org/10.3390/molecules22122213>
  • Šolínová Veronika, Mikysková Hana, Kaiser Martin Maxmilián, Janeba Zlatko, Holý Antonín, Kašička Václav: Estimation of apparent binding constant of complexes of selected acyclic nucleoside phosphonates with β‐cyclodextrin by affinity capillary electrophoresis. Electrophoresis 2016, 37, 239. <https://doi.org/10.1002/elps.201500337>
  • 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. <https://doi.org/10.1016/j.poly.2015.02.022>
  • Xia Ran, Xie Ming-Sheng, Niu Hong-Ying, Qu Gui-Rong, Guo Hai-Ming: Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water. Green Chem. 2014, 16, 1077. <https://doi.org/10.1039/C3GC41658E>
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  • Parchina Anastasia, Froeyen Matheus, Margamuljana Lia, Rozenski Jef, De Jonghe Steven, Briers Yves, Lavigne Rob, Herdewijn Piet, Lescrinier Eveline: Discovery of an Acyclic Nucleoside Phosphonate that Inhibits Mycobacterium tuberculosis ThyX Based on the Binding Mode of a 5‐Alkynyl Substrate Analogue. ChemMedChem 2013, 8, 1373. <https://doi.org/10.1002/cmdc.201300146>
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  • Manvar Atul, Shah Anamik: Diversity oriented efficient access of trisubstituted purines via sequential regioselective Mitsunobu coupling and SNAr based C6 functionalizations. Tetrahedron 2013, 69, 680. <https://doi.org/10.1016/j.tet.2012.10.079>
  • Špak Josef, Votruba Ivan, Pavingerová Daniela, Holý Antonín, Špaková Vlastimila, Petrzik Karel: Antiviral activity of acyclic nucleoside phosphonates PMEA, (S)-HPMPC, PMEDAP and ribavirin against Cauliflower mosaic virus in Brassica pekinensis. Plant Cell Tiss Organ Cult 2012, 110, 63. <https://doi.org/10.1007/s11240-012-0130-0>
  • Špak Josef, Votruba Ivan, Pavingerová Daniela, Holý Antonín, Špaková Vlastimila, Petrzik Karel: Antiviral activity of tenofovir against Cauliflower mosaic virus and its metabolism in Brassica pekinensis plants. Antiv Res 2011, 92, 378. <https://doi.org/10.1016/j.antiviral.2011.08.014>
  • Špak J., Holý A., Pavingerová D., Votruba I., Špaková V., Petrzik K.: New in vitro method for evaluating antiviral activity of acyclic nucleoside phosphonates against plant viruses. Antivir Res 2010, 88, 296. <https://doi.org/10.1016/j.antiviral.2010.09.019>
  • Hájek Miroslav, Cvilink Viktor, Votruba Ivan, Holý Antonín, Mertlíková-Kaiserová Helena: Distinct modulation of telomere length in two T-lymphoblastic leukemia cell lines by cytotoxic nucleoside phosphonates PMEG and PMEDAP. European Journal of Pharmacology 2010, 643, 6. <https://doi.org/10.1016/j.ejphar.2010.06.006>
  • Šolínová Veronika, Kašička Václav, Sázelová Petra, Holý Antonín: Chiral analysis of anti‐acquired immunodeficiency syndrome drug, 9‐(R)‐[2‐(phosphonomethoxy)propyl]adenine (tenofovir), and related antiviral acyclic nucleoside phosphonates by CE using β‐CD as chiral selector. Electrophoresis 2009, 30, 2245. <https://doi.org/10.1002/elps.200800790>
  • Keough Dianne T., Hocková Dana, Holý Antonín, Naesens Lieve M. J., Skinner-Adams Tina S., Jersey John de, Guddat Luke W.: Inhibition of Hypoxanthine-Guanine Phosphoribosyltransferase by Acyclic Nucleoside Phosphonates: A New Class of Antimalarial Therapeutics. J. Med. Chem. 2009, 52, 4391. <https://doi.org/10.1021/jm900267n>
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  • Pechar Michal, Braunová Alena, Šubr Vladimír, Ulbrich Karel, Holý Antonín: Polymeric Conjugates of 9-[2-(Phosphonomethoxy)ethyl]purine with Potential Antiviral and Cytostatic Activity. Collect. Czech. Chem. Commun. 2006, 71, 1211. <https://doi.org/10.1135/cccc20061211>
  • Česnek Michal, Masojídková Milena, Holý Antonín, Šolínová Veronika, Koval Dušan, Kašička Václav: Synthesis and Properties of 2-Guanidinopurines. Collect. Czech. Chem. Commun. 2006, 71, 1303. <https://doi.org/10.1135/cccc20061303>
  • Holý Antonin: Synthesis of Acyclic Nucleoside Phosphonates. CP Nucleic Acid Chemistry 2005, 22. <https://doi.org/10.1002/0471142700.nc1402s22>
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  • Rejman Dominik, Masojídková Milena, De Clercq Eric, Rosenberg Ivan: 2′-C-ALKOXY AND 2′-C-ARYLOXY DERIVATIVES OF N-(2-PHOSPHONOMETHOXYETHYL)-PURINES AND -PYRIMIDINES: SYNTHESIS AND BIOLOGICAL ACTIVITY. NUCLEOT NUCL 2001, 20, 1497. <https://doi.org/10.1081/NCN-100105244>
  • Janeba Zlatko, Holý Antonín, Masojídková Milena: Synthesis of 8-Amino- and N-Substituted 8-Aminoadenine Derivatives of Acyclic Nucleoside and Nucleotide Analogs. Collect. Czech. Chem. Commun. 2001, 66, 517. <https://doi.org/10.1135/cccc20010517>
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  • Krejc̆ová Romana, Horská Kvĕtoslava, Votruba Ivan, Holý Antonı́n: Interaction of guanine phosphonomethoxyalkyl derivatives with GMP kinase isoenzymes. Biochemical Pharmacology 2000, 60, 1907. <https://doi.org/10.1016/S0006-2952(00)00512-8>
  • Bacchelli Corinne, Condom Roger, Patino Nadia, Aubertin Anne-Marie: Synthesis and Biological Activities of New Carbaacyclonucleosides and 1′-Oxaacyclonucleosides Related to Clitocine. NUCLEOT NUCL 2000, 19, 567. <https://doi.org/10.1080/15257770008035008>
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  • Vargas Gabriela, Revillar Alma, Havel Josef, Holý Antonín: Capillary electrophoresis separation of the new anti‐AIDS agents 9‐(2‐phosphonylmethoxyethyl)adenine and 9‐(2‐phosphonylmethoxyethyl)‐2,6‐diaminopurine in mixtures with some monoribonucleotides or the most common deoxynucleotides. Electrophoresis 1998, 19, 2926. <https://doi.org/10.1002/elps.1150191621>
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