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Collect. Czech. Chem. Commun. 2000, 65, 1357-1373
https://doi.org/10.1135/cccc20001357

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

Michal Česnek, 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

  • Graml Andreas, Ghosh Indrajit, König Burkhard: Synthesis of Arylated Nucleobases by Visible Light Photoredox Catalysis. J. Org. Chem. 2017, 82, 3552. <https://doi.org/10.1021/acs.joc.7b00088>
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  • 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>
  • Nauš Petr, Pohl Radek, Votruba Ivan, Džubák Petr, Hajdúch Marián, Ameral Ria, Birkuš Gabriel, Wang Ting, Ray Adrian S., Mackman Richard, Cihlar Tomas, Hocek Michal: 6-(Het)aryl-7-Deazapurine Ribonucleosides as Novel Potent Cytostatic Agents. J. Med. Chem. 2010, 53, 460. <https://doi.org/10.1021/jm901428k>
  • Čerňa Igor, Pohl Radek, Klepetářová Blanka, Hocek Michal: Intramolecular Direct C−H Arylation Approach to Fused Purines. Synthesis of Purino[8,9-f]phenanthridines and 5,6-Dihydropurino[8,9-a]isoquinolines§Dedicated to the memory of Keith Fagnou. J. Org. Chem. 2010, 75, 2302. <https://doi.org/10.1021/jo100111t>
  • Qu Gui-Rong, Mao Zhi-Jie, Niu Hong-Ying, Wang Dong-Chao, Xia Chao, Guo Hai-Ming: Straightforward and Highly Efficient Catalyst-Free One-Step Synthesis of 2-(Purin-6-yl)acetoacetic Acid Ethyl Esters, (Purin-6-yl)acetates, and 6-Methylpurines through SNAr-Based Reactions of 6-Halopurines with Ethyl Acetoacetate. Org. Lett. 2009, 11, 1745. <https://doi.org/10.1021/ol9002256>
  • Bambuch Vítězslav, Pohl Radek, Hocek Michal: Synthesis of 6-(4,5-Dihydrofuran-2-yl)- and 6-(Tetrahydrofuran-2-yl)purine Bases and Nucleosides. Eur. J. Org. Chem. 2008, 2008, 2783. <https://doi.org/10.1002/ejoc.200800174>
  • Čerňa Igor, Pohl Radek, Klepetářová Blanka, Hocek Michal: Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C−H Arylation Reactions. J. Org. Chem. 2008, 73, 9048. <https://doi.org/10.1021/jo8018126>
  • Nauš Petr, Kuchař Martin, Hocek Michal: Cytostatic and Antiviral 6-Arylpurine Ribonucleosides IX. Synthesis and Evaluation of 6-Substituted 3-Deazapurine Ribonucleosides. Collect. Czech. Chem. Commun. 2008, 73, 665. <https://doi.org/10.1135/cccc20080665>
  • Schnürch Michael, Flasik Radoslav, Khan Ather Farooq, Spina Markus, Mihovilovic Marko D., Stanetty Peter: Cross‐Coupling Reactions on Azoles with Two and More Heteroatoms. Eur. J. Org. Chem. 2006, 2006, 3283. <https://doi.org/10.1002/ejoc.200600089>
  • Hocek Michal, Šilhár Peter, Shih I-hung, Mabery Eric, Mackman Richard: Cytostatic and antiviral 6-arylpurine ribonucleosides. Part 7: Synthesis and evaluation of 6-substituted purine l-ribonucleosides. Biorg Med Chem Lett 2006, 16, 5290. <https://doi.org/10.1016/j.bmcl.2006.07.092>
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  • Hocek Michal, Šilhár Peter, Pohl Radek: Cytostatic and Antiviral 6-Arylpurine Ribonucleosides VIII. Synthesis and Evaluation of 6-Substituted Purine 3'-Deoxyribonucleosides. Collect. Czech. Chem. Commun. 2006, 71, 1484. <https://doi.org/10.1135/cccc20061484>
  • Hocek Michal, Pohl Radek, Císařová Ivana: Highly Methylated Purines and Purinium Salts as Analogues of Heteromines. Eur. J. Org. Chem. 2005, 2005, 3026. <https://doi.org/10.1002/ejoc.200500154>
  • Hocek Michal, Nauš Petr, Pohl Radek, Votruba Ivan, Furman Phillip A., Tharnish Phillip M., Otto Michael J.: Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides. J. Med. Chem. 2005, 48, 5869. <https://doi.org/10.1021/jm050335x>
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  • Hocek Michal: Syntheses of Purines Bearing Carbon Substituents in Positions 2, 6 or 8 by Metal‐ or Organometal‐Mediated C−C Bond‐Forming Reactions. Eur. J. Org. Chem. 2003, 2003, 245. <https://doi.org/10.1002/ejoc.200390025>
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  • Hocek Michal, Dvořáková Hana: An Efficient Synthesis of 2-Substituted 6-Methylpurine Bases and Nucleosides by Fe- or Pd-Catalyzed Cross-Coupling Reactions of 2,6-Dichloropurines. J. Org. Chem. 2003, 68, 5773. <https://doi.org/10.1021/jo034351i>
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  • 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>
  • Lakshman Mahesh K: Palladium-catalyzed C–N and C–C cross-couplings as versatile, new avenues for modifications of purine 2′-deoxynucleosides. J Organomet Chem 2002, 653, 234. <https://doi.org/10.1016/S0022-328X(02)01267-6>
  • Havelková Martina, Dvořák Dalimil, Hocek Michal: Covalent analogues of DNA base-pairs and triplets. Part 3: Synthesis of 1,4- and 1,3-bis(purin-6-yl)benzenes and 1-(1,3-dimethyluracil-5-yl)-3 or 4-(purin-9-yl)benzenes. Tetrahedron 2002, 58, 7431. <https://doi.org/10.1016/S0040-4020(02)00833-5>
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  • 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>
  • Cesnek Michal, Hocek Michal, Holy Antonin: ChemInform Abstract: 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. ChemInform 2001, 32, no. <https://doi.org/10.1002/chin.200105206>
  • 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>
  • 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>
  • 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>