Collect. Czech. Chem. Commun.
1997, 62, 136-146
https://doi.org/10.1135/cccc19970136
Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents
Michal Hocek, Milena Masojídková 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
- Rusakova Irina L., Rusakov Yuriy Yu.: Relativistic Effects from Heavy Main Group p-Elements on the NMR Chemical Shifts of Light Atoms: From Pioneering Studies to Recent Advances. Magnetochemistry 2023, 9, 24. <https://doi.org/10.3390/magnetochemistry9010024>
- Cīrule Dace, Novosjolova Irina, Bizdēna Ērika, Turks Māris: 1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles. Beilstein J. Org. Chem. 2021, 17, 410. <https://doi.org/10.3762/bjoc.17.37>
- Novosjolova Irina, Bizdēna Ērika, Turks Māris: Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives. Eur J Org Chem 2015, 2015, 3629. <https://doi.org/10.1002/ejoc.201403527>
- 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>
- Standara Stanislav, Maliňáková Kateřina, Marek Radek, Marek Jaromír, Hocek Michal, Vaara Juha, Straka Michal: Understanding the NMR chemical shifts for 6-halopurines: role of structure, solvent and relativistic effects. Phys. Chem. Chem. Phys. 2010, 12, 5126. <https://doi.org/10.1039/b921383j>
- 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>
- Heuberger Benjamin D., Shin Dongwon, Switzer Christopher: Two Watson−Crick-Like Metallo Base-Pairs. Org. Lett. 2008, 10, 1091. <https://doi.org/10.1021/ol703029d>
- 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>
- Chinchilla Rafael, Nájera Carmen, Yus Miguel: Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry. Chem. Rev. 2004, 104, 2667. <https://doi.org/10.1021/cr020101a>
- 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>
- Hocková Dana, Holý Antonín, Masojídková Milena, Andrei Graciela, Snoeck Robert, De Clercq Erik, Balzarini Jan: 5-Substituted-2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidinesAcyclic Nucleoside Phosphonate Analogues with Antiviral Activity. J. Med. Chem. 2003, 46, 5064. <https://doi.org/10.1021/jm030932o>
- 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. Journal of Organometallic Chemistry 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>
- 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>
- 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: Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides: Application of the Suzuki−Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids. J. Med. Chem. 2000, 43, 1817. <https://doi.org/10.1021/jm991167+>
- Havelková Martina, Studenovský Martin, Dvořák Dalimil: N1-Substituted Hypoxanthine Derivatives from the Reaction of 6-Halopurines with Michael Acceptors Under the Conditions of Heck Reaction. Collect. Czech. Chem. Commun. 2000, 65, 797. <https://doi.org/10.1135/cccc20000797>
- 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>
- HOCEK M., MASOJIDKOVA M., HOLY A.: ChemInform Abstract: Synthesis of Acyclic Nucleotide Analogues Derived from 6‐ Hetarylpurines via Cross‐Coupling Reactions of 9‐(2‐( Diethoxyphosphonylmethoxy)ethyl)‐6‐iodopurine with Hetaryl Organometallic Reagents. ChemInform 1997, 28. <https://doi.org/10.1002/chin.199722241>
- Bhanu Prasad A.S, Stevenson Thomas M, Citineni Janakiram Rao, Nyzam Valérie, Knochel Paul: Preparation and reactions of new zincated nitrogen-containing heterocycles. Tetrahedron 1997, 53, 7237. <https://doi.org/10.1016/S0040-4020(97)00427-4>