Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 2001, 66, 483-499
https://doi.org/10.1135/cccc20010483

Cytostatic 6-Arylpurine Nucleosides III. Synthesis and Structure-Activity Relationship Study in Cytostatic Activity of 6-Aryl-, 6-Hetaryl- and 6-Benzylpurine Ribonucleosides

Michal Hoceka,*, Antonín Holýa, Ivan Votrubaa and Hana Dvořákováb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-166 10 Prague 6, Czech Republic
b Laboratory of NMR Spectroscopy, Institute of Chemical Technology, Prague, CZ-166 28 Prague 6, Czech Republic

Crossref Cited-by Linking

  • Liu Gang, Mu Xianfeng, Tian Miao, Wang Weili, Zou Chunhui, Chen Yiwen, Yu Mingwu: Metal‐Free, Light‐Mediated, Site‐Specific, Radical C6−H Alkylation of Purines with Alcohols Intervened by Oxalates without Catalysts. Eur J Org Chem 2023, 26. <https://doi.org/10.1002/ejoc.202201491>
  • Liu Xiguang, Sun Xiangbin, Wang Weili, Tian Miao, Chen Yiwen, Zou Chunhui, Yu Mingwu: Light, metal‐free regioselective C6‐H alkylation of purines and purine nucleosides with alcohols. Journal of Heterocyclic Chem 2023, 60, 1179. <https://doi.org/10.1002/jhet.4659>
  • Jiang Qingsong, Liu Xiguang, Wang Weili, Chen Yiwen, Yu Mingwu: Metal-free direct C-6–H alkylation of purines and purine nucleosides enabled by oxidative homolysis of 4-alkyl-1,4-dihydropyridines at room temperature. Org. Biomol. Chem. 2023, 21, 1744. <https://doi.org/10.1039/D2OB02070J>
  • Ostrowski Tomasz: Bioactive Furanyl- or Thienyl-Substituted Nucleobases, Nucleosides and Their Analogues. MRMC 2023, 23, 633. <https://doi.org/10.2174/1389557522666220812125205>
  • Mondal Manoj, Begum Tahshina, Bharali Pankaj: Regioselective C–H and N–H functionalization of purine derivatives and analogues: a synthetic and mechanistic perspective. Catal. Sci. Technol. 2018, 8, 6029. <https://doi.org/10.1039/C8CY01860J>
  • Malnuit Vincent, Slavětínská Lenka Poštová, Nauš Petr, Džubák Petr, Hajdúch Marián, Stolaříková Jiřina, Snášel Jan, Pichová Iva, Hocek Michal: 2‐Substituted 6‐(Het)aryl‐7‐deazapurine Ribonucleosides: Synthesis, Inhibition of Adenosine Kinases, and Antimycobacterial Activity. ChemMedChem 2015, 10, 1079. <https://doi.org/10.1002/cmdc.201500081>
  • D'Errico Stefano, Oliviero Giorgia, Borbone Nicola, Nici Fabrizia, Piccialli Vincenzo, Pinto Brunella, D'Alonzo Daniele, Mayol Luciano, Piccialli Gennaro: Synthesis of C6‐Pyridylpurine Nucleosides by Reaction of Nebularine N1‐Oxide with Pyridinyl Grignard Reagents. Eur J Org Chem 2015, 2015, 2244. <https://doi.org/10.1002/ejoc.201403648>
  • Rathi Anuj K., Gawande Manoj B., Zboril Radek, Varma Rajender S.: Microwave-assisted synthesis – Catalytic applications in aqueous media. Coordination Chemistry Reviews 2015, 291, 68. <https://doi.org/10.1016/j.ccr.2015.01.011>
  • Ren Hang, An Haoyun, Hatala Paul J, Stevens William C, Tao Jingchao, He Baicheng: Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides. Beilstein J. Org. Chem. 2015, 11, 2509. <https://doi.org/10.3762/bjoc.11.272>
  • Amiable Claire, Paoletti Julie, Haouz Ahmed, Padilla André, Labesse Gilles, Kaminski Pierre-Alexandre, Pochet Sylvie: 6-(Hetero)Arylpurine nucleotides as inhibitors of the oncogenic target DNPH1: Synthesis, structural studies and cytotoxic activities. European Journal of Medicinal Chemistry 2014, 85, 418. <https://doi.org/10.1016/j.ejmech.2014.07.110>
  • Nauš Petr, Caletková Olga, Konečný Petr, Džubák Petr, Bogdanová Kateřina, Kolář Milan, Vrbková Jana, Slavětínská Lenka, Tloušt’ová Eva, Perlíková Pavla, Hajdúch Marián, Hocek Michal: Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides. J. Med. Chem. 2014, 57, 1097. <https://doi.org/10.1021/jm4018948>
  • Xia Ran, Xie Ming-Sheng, Niu Hong-Ying, Qu Gui-Rong, Guo Hai-Ming: Radical Route for the Alkylation of Purine Nucleosides at C6 via Minisci Reaction. Org. Lett. 2014, 16, 444. <https://doi.org/10.1021/ol4033336>
  • Xia Ran, Xie Ming-Sheng, Niu Hong-Ying, Qu Gui-Rong, Guo Hai-Ming: Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water. Green Chem. 2014, 16, 1077. <https://doi.org/10.1039/C3GC41658E>
  • Perlíková Pavla, Eberlin Ludovic, Ménová Petra, Raindlová Veronika, Slavětínská Lenka, Tloušťová Eva, Bahador Gina, Lee Yu‐Jen, Hocek Michal: Synthesis and Cytostatic and Antiviral Activities of 2′‐Deoxy‐2′,2′‐difluororibo‐ and 2′‐Deoxy‐2′‐fluororibonucleosides Derived from 7‐(Het)aryl‐7‐deazaadenines. ChemMedChem 2013, 8, 832. <https://doi.org/10.1002/cmdc.201300047>
  • D'Errico Stefano, Oliviero Giorgia, Borbone Nicola, Piccialli Vincenzo, D'Atri Valentina, Mayol Laura, Piccialli Gennaro: Synthesis of 2,6‐Dialkyl(aryl)purine Nucleosides by Exploiting the Reactivity of Nebularine N1‐Oxide towards Grignard Reagents. Eur J Org Chem 2013, 2013, 6948. <https://doi.org/10.1002/ejoc.201300941>
  • Gurram Venkateshwarlu, Pottabathini Narender, Garlapati Ramesh, Chaudhary Avinash B., Patro Balaram, Lakshman Mahesh K.: CC Cross‐Coupling Reactions of O6‐Alkyl‐2‐Haloinosine Derivatives and a One‐Pot Cross‐Coupling/O6‐Deprotection Procedure. Chemistry — An Asian Journal 2012, 7, 1853. <https://doi.org/10.1002/asia.201200093>
  • Nauš Petr, Perlíková Pavla, Bourderioux Aurelie, Pohl Radek, Slavětínská Lenka, Votruba Ivan, Bahador Gina, Birkuš Gabriel, Cihlář Tomáš, Hocek Michal: Sugar-modified derivatives of cytostatic 7-(het)aryl-7-deazaadenosines: 2′-C-methylribonucleosides, 2′-deoxy-2′-fluoroarabinonucleosides, arabinonucleosides and 2′-deoxyribonucleosides. Bioorganic & Medicinal Chemistry 2012, 20, 5202. <https://doi.org/10.1016/j.bmc.2012.07.003>
  • Lalut Julien, Tripoteau Ludovic, Marty Christel, Bares Hugo, Bourgougnon Nathalie, Felpin François-Xavier: Synthesis of C3-arylated-3-deazauridine derivatives with potent anti-HSV-1 activities. Bioorganic & Medicinal Chemistry Letters 2012, 22, 7461. <https://doi.org/10.1016/j.bmcl.2012.10.047>
  • Hassan Abdalla E.A., Abou-Elkhair Reham A.I., Riordan James M., Allan Paula W., Parker William B., Khare Rashmi, Waud William R., Montgomery John A., Secrist John A.: Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: Palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides . Eur Med Chem 2012, 47, 167. <https://doi.org/10.1016/j.ejmech.2011.10.039>
  • Perlíková Pavla, Jornet Martínez Neus, Slavětínská Lenka, Hocek Michal: Synthesis of 2′-deoxy-2′-fluororibo- and 2′-deoxy-2′,2′-difluororibonucleosides derived from 6-(het)aryl-7-deazapurines. Tetrahedron 2012, 68, 8300. <https://doi.org/10.1016/j.tet.2012.07.033>
  • Iaroshenko Viktor O., Mkrtchyan Satenik, Gevorgyan Ashot, Miliutina Mariia, Villinger Alexander, Volochnyuk Dmytro, Sosnovskikh Vyacheslav Ya., Langer Peter: 2,3-Unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines. Org. Biomol. Chem. 2012, 10, 890. <https://doi.org/10.1039/C1OB06494K>
  • Perlíková Pavla, Pohl Radek, Votruba Ivan, Shih Robert, Birkuš Gabriel, Cihlář Tomáš, Hocek Michal: Phosphoramidate pronucleotides of cytostatic 6-aryl-7-deazapurine ribonucleosides. Bioorganic & Medicinal Chemistry 2011, 19, 229. <https://doi.org/10.1016/j.bmc.2010.11.029>
  • 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>
  • Qu Gui-Rong, Xin Peng-Yang, Niu Hong-Ying, Jin Xin, Guo Xiao-Ting, Yang Xi-Ning, Guo Hai-Ming: Microwave promoted palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of 6-chloropurines with sodium tetraarylborate in water. Tetrahedron 2011, 67, 9099. <https://doi.org/10.1016/j.tet.2011.09.082>
  • Bourderioux Aurelie, Nauš Petr, Perlíková Pavla, Pohl Radek, Pichová Iva, Votruba Ivan, Džubák Petr, Konečný Petr, Hajdúch Marián, Stray Kirsten M., Wang Ting, Ray Adrian S., Feng Joy Y., Birkus Gabriel, Cihlar Tomas, Hocek Michal: Synthesis and Significant Cytostatic Activity of 7-Hetaryl-7-deazaadenosines. J. Med. Chem. 2011, 54, 5498. <https://doi.org/10.1021/jm2005173>
  • Guo Hai-Ming, Zhang Yu, Niu Hong-Ying, Wang Dong-Chao, Chu Zhi-Liang, Qu Gui-Rong: Microwave promoted C6-alkylation of purines through SNAr-based reaction of 6-chloropurines with 3-alkyl-acetylacetone. Org Biomol Chem 2011, 9, 2065. <https://doi.org/10.1039/c0ob01213k>
  • Wang Dong-Chao, Niu Hong-Ying, Qu Gui-Rong, Liang Lei, Wei Xue-Jiao, Zhang Yang, Guo Hai-Ming: Nickel-catalyzed Negishi cross-couplings of 6-chloropurines with organozinc halides at room temperature. Biomol Chem 2011, 9, 7663. <https://doi.org/10.1039/c1ob06265d>
  • Nauš Petr, Perlíková Pavla, Pohl Radek, Hocek Michal: Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides. Collect. Czech. Chem. Commun. 2011, 76, 957. <https://doi.org/10.1135/cccc2011082>
  • Křováček Martin, Dvořáková Hana, Votruba Ivan, Císařová Ivana, Dvořák Dalimil: 6-Alkynylpurines bearing electronacceptor substituents: Preparation, reactivity in cycloaddition reactions and cytostatic activity. Collect. Czech. Chem. Commun. 2011, 76, 1487. <https://doi.org/10.1135/cccc2011176>
  • 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>
  • Spáčilová Pavla, Nauš Petr, Pohl Radek, Votruba Ivan, Snášel Jan, Zábranská Helena, Pichová Iva, Ameral Ria, Birkuš Gabriel, Cihlář Tomáš, Hocek Michal: CycloSal‐phosphate Pronucleotides of Cytostatic 6‐(Het)aryl‐7‐deazapurine Ribonucleosides: Synthesis, Cytostatic Activity, and Inhibition of Adenosine Kinases. ChemMedChem 2010, 5, 1386. <https://doi.org/10.1002/cmdc.201000192>
  • Besada Pedro, Costas Tamara, Teijeira Marta, Terán Carmen: Synthesis and cytostatic activity of purine nucleosides derivatives of allofuranose. European Journal of Medicinal Chemistry 2010, 45, 6114. <https://doi.org/10.1016/j.ejmech.2010.09.046>
  • 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>
  • Slagt Vincent F., de Vries André H. M., de Vries Johannes G., Kellogg Richard M.: Practical Aspects of Carbon−Carbon Cross-Coupling Reactions Using Heteroarenes. Org. Process Res. Dev. 2010, 14, 30. <https://doi.org/10.1021/op900221v>
  • Kotora Martin, Hocek Michal, Turek Pavel, Pohl Radek, Klepetářová Blanka, Votruba Ivan, Opekar Stanislav: [2+2+2]-Cocyclotrimerization of 6-Alkynyl-7-benzylpurines with α,ω-Diynes. HETEROCYCLES 2010, 82, 895. <https://doi.org/10.3987/COM-10-S(E)56>
  • Kang Fu‐An, Sui Zhihua, Murray William V.: Phosphonium Coupling in the Direct Bond Formations of Tautomerizable Heterocycles via C–OH Bond Activation. Eur J Org Chem 2009, 2009, 461. <https://doi.org/10.1002/ejoc.200801004>
  • 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>
  • 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>
  • Turek Pavel, Hocek Michal, Pohl Radek, Klepetářová Blanka, Kotora Martin: Cobalt‐Induced Synthesis of 6‐(Pyridin‐2‐yl)purines by Microwave‐Enhanced [2+2+2] Cyclotrimerization. Eur J Org Chem 2008, 2008, 3335. <https://doi.org/10.1002/ejoc.200800205>
  • 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>
  • Kang Fu-An, Sui Zhihua, Murray William V.: Pd-Catalyzed Direct Arylation of Tautomerizable Heterocycles with Aryl Boronic Acids via C−OH Bond Activation Using Phosphonium Salts. J. Am. Chem. Soc. 2008, 130, 11300. <https://doi.org/10.1021/ja804804p>
  • 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>
  • Hocek Michal, Šilhár Peter: Palladium‐Catalyzed Cross‐Coupling Reactions in C6 Modifications of Purine Nucleosides. CP Nucleic Acid Chemistry 2007, 28. <https://doi.org/10.1002/0471142700.nc0116s28>
  • Kimoto Michiko, Moriyama Kei, Yokoyama Shigeyuki, Hirao Ichiro: Cytostatic evaluations of nucleoside analogs related to unnatural base pairs for a genetic expansion system. Bioorganic & Medicinal Chemistry Letters 2007, 17, 5582. <https://doi.org/10.1016/j.bmcl.2007.07.088>
  • Zhu Ruizhi, Qu Fanqi, Quéléver Gilles, Peng Ling: Direct synthesis of 5-aryltriazole acyclonucleosides via Suzuki coupling in aqueous solution. Tetrahetron Lett 2007, 48, 2389. <https://doi.org/10.1016/j.tetlet.2007.01.154>
  • 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>
  • Liu Jiangqiong, Robins Morris J.: SNAr Displacements with 6-(Fluoro, Chloro, Bromo, Iodo, and Alkylsulfonyl)purine Nucleosides:  Synthesis, Kinetics, and Mechanism1. J. Am. Chem. Soc. 2007, 129, 5962. <https://doi.org/10.1021/ja070021u>
  • Kang Soon Bang, De Clercq Erik, Lakshman Mahesh K.: Pd-Catalyzed C−C Bond-Forming Reactions of Thymidine Mesitylene Sulfonate. J. Org. Chem. 2007, 72, 5724. <https://doi.org/10.1021/jo070843+>
  • Kimoto Michiko, Mitsui Tsuneo, Harada Yoko, Sato Akira, Yokoyama Shigeyuki, Hirao Ichiro: Fluorescent probing for RNA molecules by an unnatural base-pair system. Nucleic Acids Research 2007, 35, 5360. <https://doi.org/10.1093/nar/gkm508>
  • Tobrman Tomáš, Dvořák Dalimil: Reductive Dimerization of 2- and 6-Iodopurines: Side Reaction in Pd-Catalyzed Cross-Coupling of Iodopurines. Collect. Czech. Chem. Commun. 2007, 72, 1365. <https://doi.org/10.1135/cccc20071365>
  • 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>
  • Wan Jinqiao, Zhu Ruizhi, Xia Yi, Qu Fanqi, Wu Qiongyou, Yang Guangfu, Neyts Johan, Peng Ling: Synthesis of 5-aryltriazole ribonucleosides via Suzuki coupling and promoted by microwave irradiation. Tetrahetron Lett 2006, 47, 6727. <https://doi.org/10.1016/j.tetlet.2006.07.103>
  • Turek Pavel, Novák Petr, Pohl Radek, Hocek Michal, Kotora Martin: Preparation of Highly Substituted 6-Arylpurine Ribonucleosides by Ni-Catalyzed Cyclotrimerization. Scope of the Reaction. J. Org. Chem. 2006, 71, 8978. <https://doi.org/10.1021/jo061485y>
  • 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>
  • Switzer Christopher, Sinha Surajit, Kim Paul H., Heuberger Benjamin D.: A Purine‐like Nickel(II) Base Pair for DNA. Angewandte Chemie 2005, 117, 1553. <https://doi.org/10.1002/ange.200462047>
  • Switzer Christopher, Sinha Surajit, Kim Paul H., Heuberger Benjamin D.: A Purine‐like Nickel(II) Base Pair for DNA. Angew Chem Int Ed 2005, 44, 1529. <https://doi.org/10.1002/anie.200462047>
  • 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>
  • Čapek Petr, Pohl Radek, Hocek Michal: Synthesis of Enantiomerically Pure (Purin-6-yl)phenylalanines and Their Nucleosides, a Novel Type of Purine-Amino Acid Conjugates. J. Org. Chem. 2005, 70, 8001. <https://doi.org/10.1021/jo051110x>
  • Lakshman Mahesh K., Gunda Padmaja, Pradhan Padmanava: Mild and Room Temperature C−C Bond Forming Reactions of Nucleoside C-6 Arylsulfonates. J. Org. Chem. 2005, 70, 10329. <https://doi.org/10.1021/jo0513764>
  • Liu Jiangqiong, Robins Morris J.: Fluoro, Alkylsulfanyl, and Alkylsulfonyl Leaving Groups in Suzuki Cross-Coupling Reactions of Purine 2‘-Deoxynucleosides and Nucleosides. Org. Lett. 2005, 7, 1149. <https://doi.org/10.1021/ol050063s>
  • Switzer Christopher, Shin Dongwon: A pyrimidine-like nickel(ii) DNA base pair. Chem. Commun. 2005, 1342. <https://doi.org/10.1039/b415426f>
  • Šilhár Peter, Pohl Radek, Votruba Ivan, Hocek Michal: The first synthesis and cytostatic activity of novel 6-(fluoromethyl)purine bases and nucleosides. Org. Biomol. Chem. 2005, 3, 3001. <https://doi.org/10.1039/b508122j>
  • Turek Pavel, Kotora Martin, Hocek Michal, Votruba Ivan: Novel Method for Preparation of Highly Substituted 6-Arylpurines by Reactions of 6-Alkynylpurines with Zirconacyclopentadienes. Collect. Czech. Chem. Commun. 2005, 70, 339. <https://doi.org/10.1135/cccc20050339>
  • 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>
  • Itoh Takahiro, Sato Kimihiko, Mase Toshiaki: A Novel Practical Synthesis of C‐2‐Arylpurines. Adv Synth Catal 2004, 346, 1859. <https://doi.org/10.1002/adsc.200404159>
  • Gunda Padmaja, Russon Larry M., Lakshman Mahesh K.: Pd‐Catalyzed Amination of Nucleoside Arylsulfonates to yield N6‐Aryl‐2,6‐Diaminopurine Nucleosides. Angewandte Chemie 2004, 116, 6532. <https://doi.org/10.1002/ange.200460782>
  • Gunda Padmaja, Russon Larry M., Lakshman Mahesh K.: Pd-Catalyzed Amination of Nucleoside Arylsulfonates to yieldN6-Aryl-2,6-Diaminopurine Nucleosides. Angew. Chem. Int. Ed. 2004, 43, 6372. <https://doi.org/10.1002/anie.200460782>
  • Hocek Michal, Štěpnička Petr, Ludvík Jiří, Císařová Ivana, Votruba Ivan, Řeha David, Hobza Pavel: Ferrocene‐Modified Purines as Potential Electrochemical Markers: Synthesis, Crystal Structures, Electrochemistry and Cytostatic Activity of (Ferrocenylethynyl)‐ and (Ferrocenylethyl)purines. Chemistry A European J 2004, 10, 2058. <https://doi.org/10.1002/chem.200305621>
  • Hirao Ichiro, Fujiwara Tsuyoshi, Kimoto Michiko, Yokoyama Shigeyuki: Unnatural base pairs between 2- and 6-substituted purines and 2-oxo(1H)pyridine for expansion of the genetic alphabet. Bioorganic & Medicinal Chemistry Letters 2004, 14, 4887. <https://doi.org/10.1016/j.bmcl.2004.07.038>
  • Sečkářová Pavlı́na, Marek Radek, Maliňáková Kateřina, Kolehmainen Erkki, Hocková Dana, Hocek Michal, Sklenář Vladimír: Direct determination of tautomerism in purine derivatives by low-temperature NMR spectroscopy. Tetrahedron Letters 2004, 45, 6259. <https://doi.org/10.1016/j.tetlet.2004.06.088>
  • 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>
  • Turek Pavel, Kotora Martin, Tišlerová Iva, Hocek Michal, Votruba Ivan, Císařová Ivana: Cocyclotrimerization of 6-Alkynylpurines with α,ω-Diynes as a Novel Approach to Biologically Active 6-Arylpurines. J. Org. Chem. 2004, 69, 9224. <https://doi.org/10.1021/jo0486342>
  • Čapek Petr, Pohl Radek, Hocek Michal: A Facile and Efficient Synthesis of (Purin-6-yl)alanines. J. Org. Chem. 2004, 69, 7985. <https://doi.org/10.1021/jo048812r>
  • Liu Jiangqiong, Robins Morris J.: Azoles as Suzuki Cross-Coupling Leaving Groups:  Syntheses of 6-Arylpurine 2‘-Deoxynucleosides and Nucleosides from 6-(Imidazol-1-yl)- and 6-(1,2,4-Triazol-4-yl)purine Derivatives1. Org Lett 2004, 6, 3421. <https://doi.org/10.1021/ol048490d>
  • Šilhár Peter, Pohl Radek, Votruba Ivan, Hocek Michal: Facile and Efficient Synthesis of 6-(Hydroxymethyl)purines. Org. Lett. 2004, 6, 3225. <https://doi.org/10.1021/ol049059r>
  • Nauš Petr, Votruba Ivan, Hocek Michal: Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides. Collect. Czech. Chem. Commun. 2004, 69, 1955. <https://doi.org/10.1135/cccc20041955>
  • 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>
  • Hocek Michal, Votruba Ivan, Dvořáková Hana: Synthesis of carba-analogues of myoseverin by regioselective cross-coupling reactions of 2,6-dichloro-9-isopropylpurine. Tetrahedron 2003, 59, 607. <https://doi.org/10.1016/S0040-4020(02)01586-7>
  • Turek Pavel, Kotora Martin, Hocek Michal, Cı́sařová Ivana: [2+2+2]-Co-cyclotrimerization 6-alkynylpurines with diynes: a method for preparation of 6-arylpurines. Tetrahetron Lett 2003, 44, 785. <https://doi.org/10.1016/S0040-4039(02)02643-6>
  • Bråthe Anders, Gundersen Lise-Lotte, Nissen-Meyer Jon, Rise Frode, Spilsberg Bjørn: Cytotoxic activity of 6-alkynyl- and 6-alkenylpurines. Biorg Med Chem Lett 2003, 13, 877. <https://doi.org/10.1016/S0960-894X(03)00011-8>
  • Agrofoglio Luigi A., Gillaizeau Isabelle, Saito Yoshio: Palladium-Assisted Routes to Nucleosides. Chem. Rev. 2003, 103, 1875. <https://doi.org/10.1021/cr010374q>
  • Francom Paula, Robins Morris J.: Nucleic Acid Related Compounds. 118. Nonaqueous Diazotization of Aminopurine Derivatives. Convenient Access to 6-Halo- and 2,6-Dihalopurine Nucleosides and 2‘-Deoxynucleosides with Acyl or Silyl Halides1. J. Org. Chem. 2003, 68, 666. <https://doi.org/10.1021/jo020625a>
  • Tobrman Tomáš, Dvořák Dalimil: 6-Magnesiated Purines:  Preparation and Reaction with Aldehydes. Org. Lett. 2003, 5, 4289. <https://doi.org/10.1021/ol0355027>
  • 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>
  • Andresen Geir, Gundersen Lise-Lotte, Nissen-Meyer Jon, Rise Frode, Spilsberg Bjørn: Cytotoxic and Antibacterial Activity of 2-Oxopurine Derivatives. Biorg Med Chem Lett 2002, 12, 567. <https://doi.org/10.1016/S0960-894X(01)00803-4>
  • Hocek Michal, Votruba Ivan: Covalent analogues of DNA base-Pairs and triplets. Part 2: † †For Part I, see ref 1. Synthesis and cytostatic activity of bis(purin-6-yl)acetylenes,-diacetylenes and related compounds. Bioorganic & Medicinal Chemistry Letters 2002, 12, 1055. <https://doi.org/10.1016/S0960-894X(02)00077-X>
  • Gundersen Lise-Lotte, Nissen-Meyer Jon, Spilsberg Bjørn: Synthesis and Antimycobacterial Activity of 6-Arylpurines:  The Requirements for the N-9 Substituent in Active Antimycobacterial Purines. J. Med. Chem. 2002, 45, 1383. <https://doi.org/10.1021/jm0110284>
  • Lakshman Mahesh K., Thomson Paul F., Nuqui Mark A., Hilmer John H., Sevova Nonka, Boggess Bill: Facile Pd-Catalyzed Cross-Coupling of 2‘-Deoxyguanosine O6-Arylsulfonates with Arylboronic Acids. Org. Lett. 2002, 4, 1479. <https://doi.org/10.1021/ol025673w>
  • Hirao Ichiro, Ohtsuki Takashi, Fujiwara Tsuyoshi, Mitsui Tsuneo, Yokogawa Tomoko, Okuni Taeko, Nakayama Hiroshi, Takio Koji, Yabuki Takashi, Kigawa Takanori, Kodama Koichiro, Yokogawa Takashi, Nishikawa Kazuya, Yokoyama Shigeyuki: An unnatural base pair for incorporating amino acid analogs into proteins. Nat Biotechnol 2002, 20, 177. <https://doi.org/10.1038/nbt0202-177>
  • 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, Stará Irena G., Starý Ivo, Dvořáková Hana: Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil. Collect. Czech. Chem. Commun. 2002, 67, 1223. <https://doi.org/10.1135/cccc20021223>
  • Hocek Michal, Dvořáková Hana, Císařová Ivana: Covalent Analogues of DNA Base-Pairs and Triplets V. Synthesis of Purine-Purine and Purine-Pyrimidine Conjugates Connected by Diverse Types of Acyclic Carbon Linkages. Collect. Czech. Chem. Commun. 2002, 67, 1560. <https://doi.org/10.1135/cccc20021560>
  • Hocek Michal, Holy Antonin, Votruba Ivan, Dvorakova Hana: ChemInform Abstract: Cytostatic 6‐Arylpurine Nucleosides. Part 3. Synthesis and Structure—Activity Relationship Study in Cytostatic Activity of 6‐Aryl‐, 6‐Hetaryl‐, and 6‐Benzylpurine Ribonucleosides. ChemInform 2001, 32. <https://doi.org/10.1002/chin.200136221>
  • Lakshman Mahesh K., Hilmer John H., Martin Jocelyn Q., Keeler John C., Dinh Yen Q. V., Ngassa Felix N., Russon Larry M.: Palladium Catalysis for the Synthesis of Hydrophobic C-6 and C-2 Aryl 2‘-Deoxynucleosides. Comparison of C−C versus C−N Bond Formation as well as C-6 versus C-2 Reactivity. J. Am. Chem. Soc. 2001, 123, 7779. <https://doi.org/10.1021/ja0107172>