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Collect. Czech. Chem. Commun. 2000, 65, 1698-1712
https://doi.org/10.1135/cccc20001698

Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine

Zlatko Janeba*, Antonín Holý and Milena Masojídková

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

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  • Česnek Michal, Jansa Petr, Šmídková Markéta, Mertlíková‐Kaiserová Helena, Dračínský Martin, Brust Tarsis F., Pávek Petr, Trejtnar František, Watts Val J., Janeba Zlatko: Bisamidate Prodrugs of 2‐Substituted 9‐[2‐(Phosphonomethoxy)ethyl]adenine (PMEA, adefovir) as Selective Inhibitors of Adenylate Cyclase Toxin from Bordetella pertussis. ChemMedChem 2015, 10, 1351. <https://doi.org/10.1002/cmdc.201500183>
  • Sedláček Ondřej, Břehová Petra, Pohl Radek, Holý Antonín, Janeba Zlatko: The synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) derivatives by diverse cross-coupling reactions. Can. J. Chem. 2011, 89, 488. <https://doi.org/10.1139/V11-001>
  • Mieczkowski Adam, Roy Vincent, Agrofoglio Luigi A.: Preparation of Cyclonucleosides. Chem. Rev. 2010, 110, 1828. <https://doi.org/10.1021/cr900329y>
  • 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>
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  • Borrmann Thomas, Abdelrahman Aliaa, Volpini Rosaria, Lambertucci Catia, Alksnis Edgars, Gorzalka Simone, Knospe Melanie, Schiedel Anke C., Cristalli Gloria, Müller Christa E.: Structure−Activity Relationships of Adenine and Deazaadenine Derivatives as Ligands for Adenine Receptors, a New Purinergic Receptor Family. J. Med. Chem. 2009, 52, 5974. <https://doi.org/10.1021/jm9006356>
  • El Ashry E. S. H., Rashed N., Awad L. F., Ramadan E., Abdel-Maggeed S. M., Rezki N.: Novel Regioselective Hydroxyl-Alkylation of 4,5-Diphenylimidazole-2-Thione and A Competitive Intramolecular Ring Closure of the S-Hydroxyalkyl-Imidazoles to Imidazo[2,1-b]Thiazines and Thiazoles. Role of Catalyst, Microwave Irradiation, and Solid Support. Nucleos Nucleot Nuc Acids 2007, 26, 423. <https://doi.org/10.1080/15257770701426179>
  • El Ashry E. S. H., Kassem A. A., Abdel-Hamid H., Louis F. F., Khattab Sh. A. N., Aouad M. R.: Novel Regioselective Formation of S- and N-Hydroxyl-Alkyls of 5-(3-Chlorobenzo[b]Thien-2-yl)-3-Mercapto-4H-1,2,4-Triazole and A Facile Synthesis of Triazolo-Thiazoles and Thiazolo-Triazoles. Role of Catalyst and Microwave. Nucleos Nucleot Nuc Acids 2007, 26, 437. <https://doi.org/10.1080/15257770701426187>
  • Hocek Michal, Hocková Dana, Štambaský Jan: Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides. Collect. Czech. Chem. Commun. 2003, 68, 837. <https://doi.org/10.1135/cccc20030837>
  • Krečmerová Marcela, Buděšínský Miloš, Masojídková Milena, Holý Antonín: Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds. Collect. Czech. Chem. Commun. 2003, 68, 931. <https://doi.org/10.1135/cccc20030931>
  • Janeba Zlatko, Holy Antonin, Masojidkova Milena: ChemInform Abstract: Synthesis of Acyclic Nucleoside and Nucleotide Analogues Derived from 6‐Amino‐7H‐purine‐8(9H)‐thione and 8‐(Methylsulfanyl)adenine. ChemInform 2001, 32. <https://doi.org/10.1002/chin.200120195>
  • 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>
  • Janeba Zlatko, Holý Antonín, Masojídková Milena: Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives. Collect. Czech. Chem. Commun. 2001, 66, 1393. <https://doi.org/10.1135/cccc20011393>