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Collect. Czech. Chem. Commun. 1999, 64, 229-241
https://doi.org/10.1135/cccc19990229

Perfluoroalkylation of 6-Iodopurines by Trimethyl(perfluoroalkyl)silanes. Synthesis of 6-(Perfluoroalkyl)purine Bases, Nucleosides and Acyclic Nucleotide Analogues

Michal Hocek* and Antonín Holý

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

Crossref Cited-by Linking

  • Medini Hayet, Mekni Nejib Hussein, Baklouti Ahmed: Synthesis of a new bis(perfluoroalkyl oxirane) dioxyethylene ether. Journal of Taibah University for Science 2015, 9, 564. <https://doi.org/10.1016/j.jtusci.2014.10.001>
  • Mekni Nejib Hussein: Synthesis of new bis(3-perfluoroalkyl-1 H -pyrazole) polyoxyethylene. Journal of Fluorine Chemistry 2014, 168, 75. <https://doi.org/10.1016/j.jfluchem.2014.09.008>
  • Iaroshenko Viktor O., Vilches-Herrera Marcelo, Gevorgyan Ashot, Mkrtchyan Satenik, Arakelyan Knar, Ostrovskyi Dmytro, Abbasi Muhammad S.A., Supe Linda, Hakobyan Ani, Villinger Alexander, Volochnyuk Dmitriy M., Tolmachev Andrei: Design, synthesis and transformation of some heteroannulated 3-aminopyridines—purine isosteres with exocyclic nitrogen atom. Tetrahedron 2013, 69, 1217. <https://doi.org/10.1016/j.tet.2012.11.026>
  • Iaroshenko Viktor O., Ostrovskyi Dmytro, Miliutina Mariia, Maalik Aneela, Villinger Alexander, Tolmachev Andrei, Volochnyuk Dmitriy M., Langer Peter: Design and Synthesis of Polycyclic Imidazole-Containing N- Heterocycles based on CH Activation/Cyclization Reactions. Adv. Synth. Catal. 2012, n/a. <https://doi.org/10.1002/adsc.201200221>
  • Šála Michal, De Palma Armando M., Hřebabecký Hubert, Dejmek Milan, Dračínský Martin, Leyssen Pieter, Neyts Johan, Mertlíková-Kaiserová Helena, Nencka Radim: SAR studies of 9-norbornylpurines as Coxsackievirus B3 inhibitors. Bioorganic & Medicinal Chemistry Letters 2011, 21, 4271. <https://doi.org/10.1016/j.bmcl.2011.05.070>
  • Iaroshenko Viktor O., Ostrovskyi Dmytro, Petrosyan Andranik, Mkrtchyan Satenik, Villinger Alexander, Langer Peter: Synthesis of Fluorinated Purine and 1-Deazapurine Glycosides as Potential Inhibitors of Adenosine Deaminase. J. Org. Chem. 2011, 76, 2899. <https://doi.org/10.1021/jo102579g>
  • Hocek Michal, Holy Antonin: ChemInform Abstract: Perfluoroalkylation of 6-Iodopurines by Trimethyl(perfluoroalkyl)silanes. Synthesis of 6-(Perfluoroalkyl)purine Bases, Nucleosides and Acyclic Nucleotide Analogues. ChemInform 2010, 30, no. <https://doi.org/10.1002/chin.199931263>
  • Núñez María C., Pavani Maria G., Díaz-Gavilán Mónica, Rodríguez-Serrano Fernando, Gómez-Vidal José A., Marchal Juan A., Aránega Antonia, Gallo Miguel A., Espinosa Antonio, Campos Joaquín M.: Synthesis and anticancer activity studies of novel 1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)uracil and (6′-substituted)-7- or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or 9H-purines. Tetrahedron 2006, 62, 11724. <https://doi.org/10.1016/j.tet.2006.09.039>
  • Šilhár Peter, Pohl Radek, Votruba Ivan, Hocek Michal: Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides. Collect. Czech. Chem. Commun. 2005, 70, 1669. <https://doi.org/10.1135/cccc20051669>
  • Lakshman Mahesh K: Palladium-catalyzed C–N and C–C cross-couplings as versatile, new avenues for modifications of purine 2′-deoxynucleosides. Journal of Organometallic Chemistry 2002, 653, 234. <https://doi.org/10.1016/S0022-328X(02)01267-6>
  • Hocek Michal, Holý Antonín, Dvořáková Hana: Cytostatic 6-Arylpurine Nucleosides IV. Synthesis of 2-Substituted 6-Phenylpurine Ribonucleosides. Collect. Czech. Chem. Commun. 2002, 67, 325. <https://doi.org/10.1135/cccc20020325>
  • Véliz Eduardo A., Stephens Olen M., Beal Peter A.: Synthesis and Analysis of RNA Containing 6-Trifluoromethylpurine Ribonucleoside. Org. Lett. 2001, 3, 2969. <https://doi.org/10.1021/ol016295i>
  • Hocek Michal, Holý Antonín, Votruba Ivan, Dvořáková Hana: Cytostatic 6-Arylpurine Nucleosides III. Synthesis and Structure-Activity Relationship Study in Cytostatic Activity of 6-Aryl-, 6-Hetaryl- and 6-Benzylpurine Ribonucleosides. Collect. Czech. Chem. Commun. 2001, 66, 483. <https://doi.org/10.1135/cccc20010483>
  • Česnek Michal, Hocek Michal, Holý Antonín: Synthesis of Acyclic Nucleotide Analogues Derived from 2-Amino-6-C-substituted Purines via Cross-Coupling Reactions of 2-Amino-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-6-halopurines with Diverse Organometallic Reagents. Collect. Czech. Chem. Commun. 2000, 65, 1357. <https://doi.org/10.1135/cccc20001357>
  • Hocek Michal, Holý Antonín, Votruba Ivan, Dvořáková Hana: Cytostatic 6-Arylpurine Nucleosides II. Synthesis of Sugar-Modified Derivatives: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-Deoxy-β-D-ribofuranosyl)- and 9-(2,3-Dihydroxypropyl)-6-phenylpurines. Collect. Czech. Chem. Commun. 2000, 65, 1683. <https://doi.org/10.1135/cccc20001683>
  • Hocková Dana, Hocek Michal, Dvořáková Hana, Votruba Ivan: Synthesis and cytostatic activity of nucleosides and acyclic nucleoside analogues derived from 6-(trifluoromethyl)purines. Tetrahedron 1999, 55, 11109. <https://doi.org/10.1016/S0040-4020(99)00615-8>