Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1995, 60, 1390-1409
https://doi.org/10.1135/cccc19951390

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

Antonín Holý, Hana Dvořáková 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

  • Liu Xiuping, Chen Chen, Li Muzi, Li Man, Ren Jie, Zhang Qingwen: Practical Synthesis of Tenofovir Alafenamide Fumarate Inspired by New Retrosynthetic Disconnection Featuring a Novel Carbon–Phosphorus Bond Construction Methodology. Org. Process Res. Dev. 2023, 27, 1079. <https://doi.org/10.1021/acs.oprd.3c00070>
  • Li Man, Zhou Ting, Zhang Qing-Wen: Chiral Analysis of the Key Intermediates of Tenofovir Alafenamide Fumarate. Pharmaceutical Fronts 2023, 05, e38. <https://doi.org/10.1055/s-0043-1763512>
  • 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>
  • Dietz Jule-Philipp, Ferenc Dorota, Jamison Timothy F., Gupton B. Frank, Opatz Till: Di-tert-butyl Phosphonate Route to the Antiviral Drug Tenofovir. Org. Process Res. Dev. 2021, 25, 789. <https://doi.org/10.1021/acs.oprd.0c00473>
  • 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>
  • Pomeisl Karel, Beier Petr, Pohl Radek, Krečmerová Marcela: Novel and Efficient Synthesis of gem‐Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs). ChemistrySelect 2016, 1, 2102. <https://doi.org/10.1002/slct.201600445>
  • Špak Josef, Janeba Zlatko, Jansa Petr, Baszczyňski Ondřej, Pavingerová Daniela, Špaková Vlastimila: Phytotoxicity of acyclic nucleoside phosphonates in Brassica pekinensis and Solanum lycopersicum. Plant Cell Tiss Organ Cult 2016, 125, 375. <https://doi.org/10.1007/s11240-016-0942-4>
  • 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. <https://doi.org/10.1021/ol503612h>
  • 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. <https://doi.org/10.1021/ol500583d>
  • 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. <https://doi.org/10.1016/j.bmc.2012.12.044>
  • Roux Loïc, Priet Stéphane, Payrot Nadine, Weck Clément, Fournier Maëlenn, Zoulim Fabien, Balzarini Jan, Canard Bruno, Alvarez Karine: Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: Synthesis, antiviral activity and decomposition study. European Journal of Medicinal Chemistry 2013, 63, 869. <https://doi.org/10.1016/j.ejmech.2013.02.039>
  • Qiu Haixiao, Padivitage Nilusha L.T., Frink Lillian A., Armstrong Daniel W.: Enantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 4. Tetrahedron: Asymmetry 2013, 24, 1134. <https://doi.org/10.1016/j.tetasy.2013.07.019>
  • Wielgus-Kutrowska Beata, Breer Katarzyna, Hashimoto Mariko, Hikishima Sadao, Yokomatsu Tsutomu, Narczyk Marta, Dyzma Alicja, Girstun Agnieszka, Staroń Krzysztof, Bzowska Agnieszka: Trimeric purine nucleoside phosphorylase: Exploring postulated one-third-of-the-sites binding in the transition state. Bioorganic & Medicinal Chemistry 2012, 20, 6758. <https://doi.org/10.1016/j.bmc.2012.08.045>
  • Jansa Petr, Baszczyňski Ondřej, Dračínský Martin, Votruba Ivan, Zídek Zdeněk, Bahador Gina, Stepan George, Cihlar Tomas, Mackman Richard, Holý Antonín, Janeba Zlatko: A novel and efficient one-pot synthesis of symmetrical diamide (bis-amidate) prodrugs of acyclic nucleoside phosphonates and evaluation of their biological activities. European Journal of Medicinal Chemistry 2011, 46, 3748. <https://doi.org/10.1016/j.ejmech.2011.05.040>
  • Barral Karine, Weck Clément, Payrot Nadine, Roux Loic, Durafour Céline, Zoulim Fabien, Neyts Johan, Balzarini Jan, Canard Bruno, Priet Stéphane, Alvarez Karine: Acyclic nucleoside thiophosphonates as potent inhibitors of HIV and HBV replication. European Journal of Medicinal Chemistry 2011, 46, 4281. <https://doi.org/10.1016/j.ejmech.2011.06.034>
  • Elbert Tomáš, Břehová Petra, Holý Antonín: The preparation of 3H-labeled acyclic nucleoside phosphonates and study of their stability. Collect. Czech. Chem. Commun. 2010, 75, 757. <https://doi.org/10.1135/cccc2010020>
  • Votruba Ivan, Trýznová Jana, Břehová Petra, Tloušťová Eva, Horská Květoslava, Fanfrlík Jindřich, Přenosil Ondřej, Holý Antonín: Inhibition of human purine nucleoside phosphorylase by tenofovir phosphate congeners. Collect. Czech. Chem. Commun. 2010, 75, 1249. <https://doi.org/10.1135/cccc2010094>
  • 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>
  • Lambertucci Catia, Antonini Ippolito, Buccioni Michela, Ben Diego Dal, Kachare Dhuldeo D., Volpini Rosaria, Klotz Karl-Norbert, Cristalli Gloria: 8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands. Bioorganic & Medicinal Chemistry 2009, 17, 2812. <https://doi.org/10.1016/j.bmc.2009.02.030>
  • 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>
  • 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. <https://doi.org/10.1016/j.antiviral.2008.05.001>
  • Česnek Michal, Holý Antonín, Masojídková Milena, Kmoníčková Eva, Zídek Zdeněk: Synthesis of guanidino analogues of PMPDAP and their immunobiological activity. Bioorganic & Medicinal Chemistry 2008, 16, 965. <https://doi.org/10.1016/j.bmc.2007.10.010>
  • Krečmerová Marcela, Holý Antonín, Masojídková Milena: Pyrimidine Acyclic Nucleotide Analogues with Aromatic Substituents in C-5 Position. Collect. Czech. Chem. Commun. 2007, 72, 927. <https://doi.org/10.1135/cccc20070927>
  • Holý Antonin: Synthesis of Acyclic Nucleoside Phosphonates. CP Nucleic Acid Chemistry 2005, 22. <https://doi.org/10.1002/0471142700.nc1402s22>
  • Pomeisl Karel, Pohl Radek, Holý Antonín, Votruba Ivan: Simple Transformation of Thymine 1-[3-Hydroxy-2-(phosphonomethoxy)propyl] Derivatives to Their 1-[3-Fluoro-2-(phosphonomethoxy)propyl] Counterparts. Collect. Czech. Chem. Commun. 2005, 70, 1465. <https://doi.org/10.1135/cccc20051465>
  • Bzowska Agnieszka, Koellner Gertraud, Wielgus-Kutrowska Beata, Stroh Albrecht, Raszewski Grzegorz, Holý Antonin, Steiner Thomas, Frank Joachim: Crystal Structure of Calf Spleen Purine Nucleoside Phosphorylase with Two Full Trimers in the Asymmetric Unit: Important Implications for the Mechanism of Catalysis. Journal of Molecular Biology 2004, 342, 1015. <https://doi.org/10.1016/j.jmb.2004.07.017>
  • Koellner Gertraud, Stroh Albrecht, Raszewski Grzegorz, Holý Antonin, Bzowska Agnieszka: Crystal Structure of Calf Spleen Purine Nucleoside Phosphorylase in a Complex with Multisubstrate Analogue Inhibitor with 2,6-Diaminopurine Aglycone. Nucleosides, Nucleotides and Nucleic Acids 2003, 22, 1699. <https://doi.org/10.1081/NCN-120023117>
  • 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>
  • 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. Nucleosides, Nucleotides and Nucleic Acids 2000, 19, 567. <https://doi.org/10.1080/15257770008035008>
  • Krejčová Romana, Horská Květoslava, Votruba Ivan, Holý Antonín: Phosphorylation of Purine (Phosphonomethoxy)alkyl Derivatives by Mitochondrial AMP Kinase (AK2 Type) from L1210 Cells. Collect. Czech. Chem. Commun. 2000, 65, 1653. <https://doi.org/10.1135/cccc20001653>
  • 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. <https://doi.org/10.1016/S0040-4039(98)00131-2>
  • HOLY A., DVORAKOVA H., MASOJIDKOVA M.: ChemInform Abstract: Synthesis of Enantiomeric N‐(2‐Phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine Bases. Part 2. The Synthon Approach. ChemInform 1996, 27. <https://doi.org/10.1002/chin.199605253>