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Collect. Czech. Chem. Commun. 2005, 70, 103-123
https://doi.org/10.1135/cccc20050103

Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides

Hubert Hřebabecký*, Milena Masojídková and Antonín Holý

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

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  • Tănase Constantin I., Drăghici Constantin, Căproiu Miron Teodor, Shova Sergiu, Mathe Christophe, Cocu Florea G., Enache Cristian, Maganu Maria: New carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; Synthesis, X-ray crystallography and anticancer activity. Bioorganic & Medicinal Chemistry 2014, 22, 513. <https://doi.org/10.1016/j.bmc.2013.10.056>
  • Páv Ondřej, Zborníková Eva, Buděšínský Miloš, Rosenberg Ivan: A new class of phosphanucleosides containing a 3-hydroxy-1-hydroxymethylphospholane 1-oxide ring. Tetrahedron 2013, 69, 9120. <https://doi.org/10.1016/j.tet.2013.08.021>
  • Šála Michal, De Palma Armando M., Hřebabecký Hubert, Nencka Radim, Dračínský Martin, Leyssen Pieter, Neyts Johan, Holý Antonín: Design, synthesis, and biological evaluation of novel coxsackievirus B3 inhibitors. Bioorganic & Medicinal Chemistry 2010, 18, 4374. <https://doi.org/10.1016/j.bmc.2010.04.081>
  • Šála Michal, Hřebabecký Hubert, Dračínský Martin, Masojídková Milena, De Palma Armando M., Neyts Johan, Holý Antonín: Synthesis of novel racemic carbocyclic nucleosides derived from 5,6-disubstituted norbornene. Collect. Czech. Chem. Commun. 2010, 75, 1. <https://doi.org/10.1135/cccc2009116>
  • Šála Michal, Hřebabecký Hubert, Dračínský Martin, Masojídková Milena, De Palma Armando M., Neyts Johan, Holý Antonín: Norbornane as the novel pseudoglycone moiety in nucleosides. Tetrahedron 2009, 65, 9291. <https://doi.org/10.1016/j.tet.2009.09.018>
  • Hřebabecký Hubert, Dračínský Martin, De Palma Armando M., Neyts Johan, Holý Antonín: Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses. Collect. Czech. Chem. Commun. 2009, 74, 469. <https://doi.org/10.1135/cccc2008193>
  • Hřebabecký Hubert, Dračínský Martin, De Palma Armando M., Neyts Johan, Holý Antonín: Synthesis of novel carbocyclic nucleoside analogues derived from 7-oxabicyclo[2.2.1]heptane-2-methanol. Collect. Czech. Chem. Commun. 2009, 74, 487. <https://doi.org/10.1135/cccc2008204>
  • Hřebabecký Hubert, Dračínský Martin, Holý Antonín: New carbocyclic nucleoside analogues built on a bicyclo[2.2.2]octane-2,2-dimethanol template. Collect. Czech. Chem. Commun. 2009, 74, 1425. <https://doi.org/10.1135/cccc2009090>
  • Hřebabecký Hubert, Dračínský Martin, Holý Antonín: Synthesis of Novel Carbocyclic Nucleoside Analogues Containing Bicyclo[2.2.1]hept-2-ene-2-methanol. Collect. Czech. Chem. Commun. 2008, 73, 44. <https://doi.org/10.1135/cccc20080044>
  • Hřebabecký Hubert, Dračínský Martin, Holý Antonín: Synthesis of Novel Carbocyclic Nucleosides and Pro-Tides Derived from 4-Oxatricyclo[4.2.1.03,7]nonane-9-methanol. Collect. Czech. Chem. Commun. 2007, 72, 1331. <https://doi.org/10.1135/cccc20071331>
  • Dejmek Milan, Hřebabecký Hubert, Dračínský Martin, Holý Antonín: Synthesis of Novel Carbocyclic Nucleoside Analogues Derived from 2-(Hydroxymethyl)bicyclo[2.2.1]heptane. Collect. Czech. Chem. Commun. 2007, 72, 1523. <https://doi.org/10.1135/cccc20071523>
  • Šála Michal, Hřebabecký Hubert, Masojídková Milena, Holý Antonín: Synthesis of Novel Racemic Conformationally Locked Carbocyclic Nucleosides Derived from 7-Substituted Bicyclo[2.2.1]hept-5-ene-2,2-dimethanols. Collect. Czech. Chem. Commun. 2006, 71, 635. <https://doi.org/10.1135/cccc20060635>
  • Hřebabecký Hubert, Masojídková Milena, Dračínský Martin, Holý Antonín: Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol. Collect. Czech. Chem. Commun. 2006, 71, 871. <https://doi.org/10.1135/cccc20060871>
  • Hrebabecky Hubert, Masojidkova Milena, Holy Antonin: Synthesis of Racemic 9‐(6‐ and 2,6‐Substituted 9H‐purin‐9‐yl)‐5‐oxatricyclo[4.2.1.03,7]nonane‐3‐methanols, Novel Conformationally Locked Carbocyclic Nucleosides. ChemInform 2005, 36. <https://doi.org/10.1002/chin.200526141>
  • Hřebabecký Hubert, Masojídková Milena, Holý Antonín: Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 5,5- and 6,6-Bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol. Collect. Czech. Chem. Commun. 2005, 70, 519. <https://doi.org/10.1135/cccc20050519>