Collect. Czech. Chem. Commun.
1987, 52, 2792-2800
https://doi.org/10.1135/cccc19872792
Synthesis of potential prodrugs and metabolites of 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)adenine
Ivan Rosenberg and Antonín Holý
Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
Crossref Cited-by Linking
- Groaz Elisabetta, De Jonghe Steven: Overview of Biologically Active Nucleoside Phosphonates. Front. Chem. 2021, 8. <https://doi.org/10.3389/fchem.2020.616863>
- Zhou Peng, Xie Ming‐Sheng, Qu Gui‐Rong, Li Ren‐Long, Guo Hai‐Ming: Synthesis of Acyclic Nucleoside Analogues through the Insertion of Carbenoids into N−H Bond of Nucleobases. Asian J Org Chem 2016, 5, 1100. <https://doi.org/10.1002/ajoc.201600251>
- Kaiser Martin Maxmilian, Jansa Petr, Dračínský Martin, Janeba Zlatko: A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid. Tetrahedron 2012, 68, 4003. <https://doi.org/10.1016/j.tet.2012.03.066>
- Ruiz Jacqueline, Beadle James R., Mark Buller R., Schreiwer Jill, Prichard Mark N., Keith Kathy A., Lewis Kenneth C., Hostetler Karl Y.: Synthesis, metabolic stability and antiviral evaluation of various alkoxyalkyl esters of cidofovir and 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine. Bioorganic & Medicinal Chemistry 2011, 19, 2950. <https://doi.org/10.1016/j.bmc.2011.03.034>
- Zakharova Valeria M., Serpi Michaela, Krylov Ivan S., Peterson Larryn W., Breitenbach Julie M., Borysko Katherine Z., Drach John C., Collins Mindy, Hilfinger John M., Kashemirov Boris A., McKenna Charles E.: Tyrosine-Based 1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) Prodrugs: Synthesis, Stability, Antiviral Activity, and in Vivo Transport Studies. J. Med. Chem. 2011, 54, 5680. <https://doi.org/10.1021/jm2001426>
- Janeba Zlatko, Masojídková Milena, Holý Antonín: Alternative synthesis of 9-{3-[(diisopropoxyphosphoryl)methoxy]-2-hydroxypropyl}adenine and its free phosphonates substituted at the C-8 position of purine base. Collect. Czech. Chem. Commun. 2010, 75, 371. <https://doi.org/10.1135/cccc2009569>
- Morrey John D., Korba Brent E., Beadle James R., Wyles David L., Hostetler Karl Y.: Alkoxyalkyl Esters of 9-( S )-(3-Hydroxy-2-Phosphonomethoxypropyl) Adenine Are Potent and Selective Inhibitors of Hepatitis B Virus (HBV) Replication In Vitro and in HBV Transgenic Mice In Vivo. Antimicrob Agents Chemother 2009, 53, 2865. <https://doi.org/10.1128/AAC.00114-09>
- Tammewar Ajay M., Cheng Lingyun, Hostetler Karl Y., Falkenstein Iryna, Beadle James R., Barron Erin C., Kozak Igor, Freeman William R.: Intraocular Properties of An Alkoxyalkyl Derivative of Cyclic 9-(S)-(3-Hydroxyl-2-Phosphonomehoxypropyl) Adenine, An Intravitreally Injectable Anti-HCMV Drug in Rabbit and Guinea Pig. Journal of Ocular Pharmacology and Therapeutics 2007, 23, 433. <https://doi.org/10.1089/jop.2007.0018>
- Zakirova N.F., Shipitsyn A.V., Belanov E.F., Jasko M.V.: A new approach to the synthesis of optically active alkylated adenine derivatives. Biorg Med Chem Lett 2004, 14, 3357. <https://doi.org/10.1016/j.bmcl.2003.12.107>
- Krečmerová Marcela, Masojídková Milena, Holý Antonín: Synthesis of N9- and N7-[2-Hydroxy-3-(phosphonomethoxy)propyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds. Collect. Czech. Chem. Commun. 2004, 69, 1889. <https://doi.org/10.1135/cccc20041889>
- Otmar Miroslav, Masojídková Milena, Votruba Ivan, Holý Antonín: An Alternative Synthesis of HPMPC and HPMPA Diphosphoryl Derivatives. Collect. Czech. Chem. Commun. 2001, 66, 500. <https://doi.org/10.1135/cccc20010500>
- Mikhailopulo Igor A., Kulak Tamara I., Tkachenko Olga V., Sentyureva Svetlana L., Victorova Lyubov S., Rosemeyer Helmut, Seela Frank: Pyrophosphoryl Derivatives of 1-(2-Deoxy-3-O-Phosphonomethyl-β-and-α-D-Erythro-Pentofuranosyl)Thymine: Synthesis and Substrate Properties Towards Some DNA Polymerases. Nucleosides, Nucleotides and Nucleic Acids 2000, 19, 1885. <https://doi.org/10.1080/15257770008045467>
- Birkuš Gabriel, Votruba Ivan, Holý Antonı́n, Otová Berta: 9-[2-(phosphonomethoxy)ethyl]adenine diphosphate (PMEApp) as a substrate toward replicative DNA polymerases α, δ, ε, and ε∗. Biochemical Pharmacology 1999, 58, 487. <https://doi.org/10.1016/S0006-2952(99)00118-5>
- Lang J, Chmelová K, Štěpánek J, Kowalewski J, Holý A: Applicability of spectroscopic methods in the investigation of transition metal cation binding to adenine mononucleotides and their analogues. Journal of Molecular Structure 1999, 480-481, 363. <https://doi.org/10.1016/S0022-2860(98)00818-7>
- Krise Jeffrey P., Stella Valentino J.: Prodrugs of phosphates, phosphonates, and phosphinates. Adv Drug Delivery Rev 1996, 19, 287. <https://doi.org/10.1016/0169-409X(95)00111-J>
- Kaminsky Ronald, Schmid Cecile, Grether Yvonne, HolY Antonin, Clercq Erik De, Naesens Lieve, Brun Reto: (S)‐9‐(3‐hydroxy‐2‐phosphonylmethoxypropyl)adenine [(S)‐HPMPA]: a purine analogue with trypanocidal activity in vitro and in vivo. Tropical Med Int Health 1996, 1, 255. <https://doi.org/10.1111/j.1365-3156.1996.tb00036.x>
- Lazrek H. B., Khaider H., Rochdi A., Barascut J. L., Imbach J. L.: Synthesis of the Nucleotide Analogue: (R,S)-9-[1-(2-Hydroxyethylthio)-2-phosphonylethyl] Adenine. Nucleosides and Nucleotides 1994, 13, 811. <https://doi.org/10.1080/15257779408013280>
- Villemin Didier, Thibault-Starzyk Frédéric: Synthesis of a New Sulfur Analog of PMEA. Synth Common 1993, 23, 1053. <https://doi.org/10.1080/00397919308018581>
- Azymah Muhammad, Chavis Claude, Lucas Marc, Morvan François, Imbach Jean-Louis: Isotactic Glycero Oligothymidylate. a Convenient Preparation of (R) and (S) 1′, 2′-Seco 2′-Nor Thymidine. Nucleosides and Nucleotides 1992, 11, 1241. <https://doi.org/10.1080/07328319208018339>
- Foster S A, Cerny J, Cheng Y C: Herpes simplex virus-specified DNA polymerase is the target for the antiviral action of 9-(2-phosphonylmethoxyethyl)adenine. Journal of Biological Chemistry 1991, 266, 238. <https://doi.org/10.1016/S0021-9258(18)52426-1>
- Holý A., Votruba I., Merta A., Černý J., Veselý J., Vlach J., Šedivá K., Rosenberg I., Otmar M., Hřebabecký H.: Acyclic nucleotide analogues: Synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro. Antivir Res 1990, 13, 295. <https://doi.org/10.1016/0166-3542(90)90014-X>
- ROSENBERG I., HOLY A.: ChemInform Abstract: Acyclic Nucleotide Analogues. Part 2. Synthesis of Potential Prodrugs and Metabolites of 9‐(S)‐(3‐Hydroxy‐2‐phosphonylmethoxypropyl)adenine. ChemInform 1988, 19. <https://doi.org/10.1002/chin.198811349>