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Collect. Czech. Chem. Commun. 1990, 55, 809-818
https://doi.org/10.1135/cccc19900809

Synthesis of N-(2-(2-phosphonylethoxy)ethyl) 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

  • Keough Dianne T., Hocková Dana, Rejman Dominik, Špaček Petr, Vrbková Silvie, Krečmerová Marcela, Eng Wai Soon, Jans Harmen, West Nicholas P., Naesens Lieve M. J., de Jersey John, Guddat Luke W.: Inhibition of the Escherichia coli 6-Oxopurine Phosphoribosyltransferases by Nucleoside Phosphonates: Potential for New Antibacterial Agents. J. Med. Chem. 2013, 56, 6967. <https://doi.org/10.1021/jm400779n>
  • Baszczyňski Ondřej, Jansa Petr, Dračínský Martin, Kaiser Martin Maxmilian, Špaček Petr, Janeba Zlatko: An efficient oxa-Michael addition to diethyl vinylphosphonate under mild reaction conditions. RSC Adv. 2012, 2, 1282. <https://doi.org/10.1039/C2RA00938B>
  • Hocková Dana, Holý Antonín, Andrei Graciela, Snoeck Robert, Balzarini Jan: Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity. Bioorganic & Medicinal Chemistry 2011, 19, 4445. <https://doi.org/10.1016/j.bmc.2011.06.045>
  • 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>
  • Fernández-Botello Alfonso, Griesser Rolf, Holý Antonín, Moreno Virtudes, Sigel Helmut: Acid−Base and Metal-Ion-Binding Properties of 9-[2-(2-Phosphonoethoxy)ethyl]adenine (PEEA), a Relative of the Antiviral Nucleotide Analogue 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA). An Exercise on the Quantification of Isomeric Complex Equilibria in Solution. Inorg. Chem. 2005, 44, 5104. <https://doi.org/10.1021/ic050341j>
  • Novák Jan, Linhart Igor, Dvorˇáková Hana: Syntheses of 7‐(2‐Hydroxy‐1‐phenylethyl)‐ and 7‐(2‐Hydroxy‐2‐phenylethyl)guanine, DNA Adducts Derived from Styrene 7,8‐Oxide. Eur J Org Chem 2004, 2004, 2738. <https://doi.org/10.1002/ejoc.200300811>
  • Gómez-Coca Raquel B., Kapinos Larisa E., Holý Antonín, Vilaplana Rosario A., González-Vílchez Francisco, Sigel Helmut: Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). J Biol Inorg Chem 2004, 9, 961. <https://doi.org/10.1007/s00775-004-0591-7>
  • Fernández-Botello Alfonso, Holý Antonı́n, Moreno Virtudes, Sigel Helmut: Intramolecular stacking interactions in ternary copper(II) complexes formed by a heteroaromatic amine and 9-[2-(2-phosphonoethoxy)ethyl]adenine, a relative of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine. Journal of Inorganic Biochemistry 2004, 98, 2114. <https://doi.org/10.1016/j.jinorgbio.2004.08.001>
  • Gómez‐Coca Raquel B., Holý Antonín, Vilaplana Rosario A., González‐Vílchez Francisco, Sigel Helmut: Solution Structures of Binary and Ternary Metal Ion Complexes of 9‐(5‐Phosphonopentyl)adenine (3′‐deoxa‐PEEA). A Nucleotide Analogue Related to the Antivirally Active 9‐[2‐(Phosphonomethoxy)ethyl]adenine (PMEA). Eur J Inorg Chem 2003, 2003, 2937. <https://doi.org/10.1002/ejic.200300100>
  • 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. <https://doi.org/10.1135/cccc20011545>
  • HOLY A., ROSENBERG I., DVORAKOVA H.: ChemInform Abstract: Acyclic Nucleotide Analogues. Part 8. Synthesis of N‐(2‐(2‐Phosphonylethoxy)ethyl) Derivatives of Heterocyclic Bases. ChemInform 1990, 21. <https://doi.org/10.1002/chin.199027337>
  • Holý A., Votruba I., Merta A., Černý J., Veselý J., Vlach J., Šedivá K., Rosenberg I., Otmar M., Hřebabecký H., Trávníĉek M., Vonka V., Snoeck R., De Clercq E.: Acyclic nucleotide analogues: Synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro. Antiviral Research 1990, 13, 295. <https://doi.org/10.1016/0166-3542(90)90014-X>