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Collect. Czech. Chem. Commun. 2005, 70, 1669-1695
https://doi.org/10.1135/cccc20051669

Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides

Peter Šilhár, Radek Pohl, Ivan Votruba and Michal Hocek*

Centre for New Antivirals and Antineoplastics, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic

Crossref Cited-by Linking

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  • Xiao Chuan, Sun Chao, Han Weiwei, Pan Feng, Dan Zhu, Li Yu, Song Zhi-Guang, Jin Ying-Hua: Synthesis of 6-(het) ary Xylocydine analogues and evaluating their inhibitory activities of CDK1 and CDK2 in vitro. Bioorganic & Medicinal Chemistry 2011, 19, 7100. <https://doi.org/10.1016/j.bmc.2011.10.003>
  • 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>
  • Hasník Zbyněk, Pohl Radek, Hocek Michal: Synthesis of (purin-6-yl)methylphosphonate bases and nucleosides. Tetrahedron Letters 2010, 51, 2464. <https://doi.org/10.1016/j.tetlet.2010.02.167>
  • 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>
  • 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>
  • Hasník Zbyněk, Pohl Radek, Klepetářová Blanka, Hocek Michal: Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines. Collect. Czech. Chem. Commun. 2009, 74, 1035. <https://doi.org/10.1135/cccc2009042>
  • Šilhár Peter, Hocek Michal, Pohl Radek, Votruba Ivan, Shih I-hung, Mabery Eric, Mackman Richard: Synthesis, cytostatic and anti-HCV activity of 6-(N-substituted aminomethyl)-, 6-(O-substituted hydroxymethyl)- and 6-(S-substituted sulfanylmethyl)purine nucleosides. biorg med chem 2008, 16, 2329. <https://doi.org/10.1016/j.bmc.2007.11.067>
  • Kuchař Martin, Pohl Radek, Klepetářová Blanka, Hocek Michal: Synthesis of diverse 6-(1,2-disubstituted ethyl)purine bases and nucleosides via 6-(oxiran-2-yl)purines. Tetrahedron 2008, 64, 10355. <https://doi.org/10.1016/j.tet.2008.08.074>
  • 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>
  • Kuchař Martin, Pohl Radek, Klepetářová Blanka, Votruba Ivan, Hocek Michal: Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations. Org. Biomol. Chem. 2008, 6, 2377. <https://doi.org/10.1039/b802833h>
  • 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>
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  • Bambuch Vítězslav, Otmar Miroslav, Pohl Radek, Masojídková Milena, Holý Antonín: C-Functionalization of 9-deazapurines by cross-coupling reactions. Tetrahedron 2007, 63, 1589. <https://doi.org/10.1016/j.tet.2006.12.008>
  • Hasník Zbyněk, Šilhár Peter, Hocek Michal: Synthesis of (purin-6-yl)acetates and 6-(2-hydroxyethyl)purines via cross-couplings of 6-chloropurines with the Reformatsky reagent. Tetrahetron Lett 2007, 48, 5589. <https://doi.org/10.1016/j.tetlet.2007.06.053>
  • Silhar Peter, Pohl Radek, Votruba Ivan, Hocek Michal: Synthesis of 2‐Substituted 6‐(Hydroxymethyl)purine Bases and Nucleosides. ChemInform 2006, 37. <https://doi.org/10.1002/chin.200616199>
  • Kuchař Martin, Pohl Radek, Votruba Ivan, Hocek Michal: Synthesis of Purines Bearing Functionalized C‐Substituents by the Conjugate Addition of Nucleophiles to 6‐Vinylpurines and 6‐Ethynylpurines. Eur J Org Chem 2006, 2006, 5083. <https://doi.org/10.1002/ejoc.200600545>
  • 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>
  • Čapek Petr, Pohl Radek, Hocek Michal: Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines. Org. Biomol. Chem. 2006, 4, 2278. <https://doi.org/10.1039/B604010A>
  • Šilhár Peter, Pohl Radek, Votruba Ivan, Klepetářová Blanka, Hocek Michal: Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides. Collect. Czech. Chem. Commun. 2006, 71, 788. <https://doi.org/10.1135/cccc20060788>
  • Lin Xiaoyu, Robins Morris J.: Nucleic Acid Related Compounds. 136. Synthesis of 2-Amino- and 2,6-Diaminopurine Derivatives via Inverse-Electron-Demand Diels-Alder Reactions. Collect. Czech. Chem. Commun. 2006, 71, 1029. <https://doi.org/10.1135/cccc20061029>
  • 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>