Collect. Czech. Chem. Commun. 2008, 73, 665-678
https://doi.org/10.1135/cccc20080665

Cytostatic and Antiviral 6-Arylpurine Ribonucleosides IX. Synthesis and Evaluation of 6-Substituted 3-Deazapurine Ribonucleosides

Petr Nauš, Martin Kuchař and Michal Hocek*

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

Individual author index pages


Other CCCC articles of these authors

  • Michal Česnek, Michal Hocek and Antonín Holý
    Cross-coupling reactions of 2-amino-6-halopurine derivatives with organometallic reagents leading to 6-alkylated purine acyclic nucleotide analogues
    Symposium Series 1999, Vol. 2, pp. 255–256 [Abstract]
    Published online 2016-05-08 23:31:50
  • Michal Hocek, Martina Havelková, Dalimil Dvořák, Antonín Holý and Ivan Votruba
    Synthesis of 6-phenylpurine bases and nucleosides by Suzuki–Miyaura cross-coupling reactions of 6-chloropurines with substituted phenylboronic acids
    Symposium Series 1999, Vol. 2, pp. 27–30 [Abstract]
    Published online 2016-05-08 20:40:17
  • Pavel Turek, Michal Hocek and Martin Kotora
    [2+2+2]-co-Cyclotrimerization of 6-alkynylpurines with diynes: A method for preparation 6-arylpurines
    Symposium Series 2002, Vol. 5, pp. 389–390 [Abstract]
    Published online 2016-01-25 20:52:00
  • Michal Hocek
    Synthesis of carba-analogues of myoseverin
    Symposium Series 2002, Vol. 5, pp. 324–325 [Abstract]
    Published online 2016-01-25 20:42:22
  • Michal Hocek, Dalimil Dvořák and Martina Havelková
    Covalently linked purine dimers or trimers and purine–pyrimidine conjugates – analogues of nucleobase-pairs or triplets
    Symposium Series 2002, Vol. 5, pp. 36–37 [Abstract]
    Published online 2016-01-25 20:38:15
  • Milan Vrabel, Ivan Rosenberg and Michal Hocek
    Synthesis of modified nucleosides and oligonucleotides bearing bipyridine or phenanthroline ligands
    Symposium Series 2005, Vol. 7, pp. 485–486 [Abstract]
    Published online 2015-11-08 11:58:56
  • Petr Novák, Michal Hocek and Martin Kotora
    Synthesis of C-arylribosides by catalytic [2+2+2]-cyclotrimerization reaction
    Symposium Series 2005, Vol. 7, pp. 445–446 [Abstract]
    Published online 2015-11-08 11:57:49
  • Martin Kuchař and Michal Hocek
    Synthesis of purines bearing functionalized C-substituents by nucleophilic additions to 6-ethynyl- or 6-vinylpurines
    Symposium Series 2005, Vol. 7, pp. 423–424 [Abstract]
    Published online 2015-11-08 11:57:11
  • Pavel Turek, Michal Hocek and Martin Kotora
    Cocyclotrimerization of 6-alkynylpurines with diynes as a novel approach to biologically active 6-arylpurines
    Symposium Series 2005, Vol. 7, pp. 279–282 [Abstract]
    Published online 2015-11-08 11:53:57
  • Jan Štambaský, Pavel Kočovský and Michal Hocek
    Towards a novel approach to C-nucleosides
    Symposium Series 2005, Vol. 7, pp. 277–278 [Abstract]
    Published online 2015-11-08 11:53:52
  • Peter Šilhár, Radek Pohl, Ivan Votruba and Michal Hocek
    Synthesis and transformations of 6-(hydroxymethyl)purines
    Symposium Series 2005, Vol. 7, pp. 221–224 [Abstract]
    Published online 2015-11-08 11:52:45
  • Petr Čapek and Michal Hocek
    Synthesis of (purin-6-yl)amino acids
    Symposium Series 2005, Vol. 7, pp. 217–220 [Abstract]
    Published online 2015-11-08 11:52:40
  • Michal Hocek and Dana Hocková
    Regioselective cross-coupling reactions in the synthesis of multisubstituted purine bases and nucleosides
    Symposium Series 2005, Vol. 7, pp. 213–216 [Abstract]
    Published online 2015-11-08 11:52:35
  • Martin Štefko and Michal Hocek
    A modular methodology for the synthesis of 3- and 4-substituted benzene and aniline C-ribonucleosides
    Symposium Series 2008, Vol. 10, pp. 455–456 [Abstract]
    Published online 2015-10-30 18:45:05
  • Jan Riedl and Michal Hocek
    Synthesis of modified fluorescent nucleosides
    Symposium Series 2008, Vol. 10, pp. 442–443 [Abstract]
    Published online 2015-10-30 18:44:40
  • Lubica Kalachova and Michal Hocek
    Synthesis of modified nucleosides and nucleoside triphosphates bearing oligopyridine ligands
    Symposium Series 2008, Vol. 10, pp. 366–368 [Abstract]
    Published online 2015-10-30 18:42:13
  • Zbyněk Hasník and Michal Hocek
    Synthesis of (purin-6-yl)acetates and their transformations
    Symposium Series 2008, Vol. 10, pp. 352–354 [Abstract]
    Published online 2015-10-30 18:41:46
  • Igor Čerňa and Michal Hocek
    Direct C–H arylation of purines and purine nucleosides
    Symposium Series 2008, Vol. 10, pp. 327–329 [Abstract]
    Published online 2015-10-30 18:40:48
  • Jan Bárta and Michal Hocek
    Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides
    Symposium Series 2008, Vol. 10, pp. 313–314 [Abstract]
    Published online 2015-10-30 18:40:16
  • Milan Vrabel and Michal Hocek
    Synthesis of modified nucleosides, nucleotides and oligonucleotides bearing metal complexes
    Symposium Series 2008, Vol. 10, pp. 182–185 [Abstract]
    Published online 2015-10-30 18:37:15
  • Hana Cahová, Luděk Havran, Petra Brázdilová, Hana Pivoňková, Miroslav Fojta and Michal Hocek
    Aminophenyl- and nitrophenyl-labeled DNA. Synthesis by polymerase incorporation of nucleoside triphosphates and electrochemical properties
    Symposium Series 2008, Vol. 10, pp. 178–181 [Abstract]
    Published online 2015-10-30 18:37:09
  • Nicolas Joubert, Jan Bárta, Milan Urban and Michal Hocek
    Modular methodology for the syntheses of various aryl C-2'-deoxyribonucleosides
    Symposium Series 2008, Vol. 10, pp. 173–177 [Abstract]
    Published online 2015-10-30 18:37:03
  • Petr Novák, Michal Hocek and Martin Kotora
    New approaches to synthesis of C-deoxyribosides starting from C-alkynyldeoxyribosides
    Symposium Series 2008, Vol. 10, pp. 168–172 [Abstract]
    Published online 2015-10-30 18:36:57
  • Michal Hocek, Peter Šilhár, Martin Kuchař, Zbyněk Hasník and Vítězslav Bambuch
    Purine bases and nucleosides bearing functionalized C-substituents in position 6. Synthesis and biological activities
    Symposium Series 2008, Vol. 10, pp. 164–167 [Abstract]
    Published online 2015-10-30 18:36:52
  • Michal Tichý and Michal Hocek
    Synthesis of 4-(het)aryl pyrimido[4,5-b]indole ribonucleosides
    Symposium Series 2011, Vol. 12, pp. 475–476 [Abstract]
    Published online 2015-08-20 10:24:59
  • Veronika Raindlová and Michal Hocek
    Direct enzymatic synthesis of aldehyde-functionalized DNA and its conjugation with hydrazines and amines
    Symposium Series 2011, Vol. 12, pp. 441–443 [Abstract]
    Published online 2015-08-20 10:23:46
  • Hana Pivoňková, Kateřina Němcová, Petra Horáková, Luděk Havran, Hana Macíčková-Cahová, Michal Hocek and Miroslav Fojta
    Tail labelled oligonucleotide probes for the detection of DNA-protein interactions
    Symposium Series 2011, Vol. 12, pp. 435–437 [Abstract]
    Published online 2015-08-20 10:23:34
  • Pavel Kielkowski and Michal Hocek
    Polymerase synthesis of modified DNA containing cytosine in major groove
    Symposium Series 2011, Vol. 12, pp. 359–360 [Abstract]
    Published online 2015-08-20 10:19:01
  • Lubica Kalachova and Michal Hocek
    Synthesis of nucleotides bearing oligopyridine ligands and their incorporation into DNA
    Symposium Series 2011, Vol. 12, pp. 357–358 [Abstract]
    Published online 2015-08-20 10:18:56
  • Miroslava Čerňová and Michal Hocek
    Dichotomy in regioselectivity of Pd-catalyzed direct C–H arylation of protected uracils
    Symposium Series 2011, Vol. 12, pp. 314–316 [Abstract]
    Published online 2015-08-20 10:12:11
  • Jan Bárta and Michal Hocek
    Modular synthesis of 5-substituted thiophene and furan C-nucleosides and their analogues
    Symposium Series 2011, Vol. 12, pp. 300–301 [Abstract]
    Published online 2015-08-20 10:11:36
  • Jana Balintová, Luděk Havran, Miroslav Fojta and Michal Hocek
    Synthesis of nucleosides and nucleoside triphosphates bearing anthraquinone substituents as redox probes and their enzymatic incorporation to DNA
    Symposium Series 2011, Vol. 12, pp. 297–299 [Abstract]
    Published online 2015-08-20 10:11:31
  • Jan Riedl and Michal Hocek
    Synthesis of biaryl-substituted fluorescent nucleosides and nucleoside triphosphates and their incorporation to DNA
    Symposium Series 2011, Vol. 12, pp. 233–235 [Abstract]
    Published online 2015-08-20 10:02:23
  • Pavla Perlíková, Petr Nauš, Aurelie Bourderioux and Michal Hocek
    Hetaryl derivatives of 7-deazapurine ribonucleosides: potent cytostatic agents
    Symposium Series 2011, Vol. 12, pp. 194–198 [Abstract]
    Published online 2015-08-20 10:00:49
  • Tomáš Kubelka, Martin Štefko, Jan Bárta, Nicolas Joubert, Milan Urban, Hubert Chapuis and Michal Hocek
    Development of a general and modular approach to C-nucleosides
    Symposium Series 2011, Vol. 12, pp. 180–183 [Abstract]
    Published online 2015-08-20 10:00:32
  • Miroslav Fojta, Luděk Havran, Petra Horáková, Hana Pivoňková, Pavel Kostečka, Hana Macíčková, Veronika Raindlová, Milan Vrabel and Michal Hocek
    Redox labelling of nucleic acids for analyzing nucleotide sequences and monitoring DNA-protein interactions
    Symposium Series 2011, Vol. 12, pp. 155–158 [Abstract]
    Published online 2015-08-20 09:59:54
  • Michal Hocek, Hana Macíčková-Cahová, Pavel Kielkowski, Veronika Raindlová, Lubica Kalachova, Jan Riedl, Jana Balintová and Petra Ménová
    Polymerase construction of base-modified DNA for chemical biology
    Symposium Series 2011, Vol. 12, pp. 152–154 [Abstract]
    Published online 2015-08-20 09:59:48
  • Zuzana Vaníková and Michal Hocek
    Polymerase synthesis of new photocaged DNA
    Symposium Series 2014, Vol. 14, pp. 392–393 [Abstract]
    Published online 2015-07-06 23:09:39
  • Michal Tichý and Michal Hocek
    Synthesis and biological activity of thiophene fused 7-deazapurine ribonucleosides
    Symposium Series 2014, Vol. 14, pp. 385–386 [Abstract]
    Published online 2015-07-06 23:09:23
  • Anna Simonova, Luděk Havran, Miroslav Fojta and Michal Hocek
    New oxidative labels for electrochemical detection of DNA
    Symposium Series 2014, Vol. 14, pp. 365–366 [Abstract]
    Published online 2015-07-06 23:08:32
  • Petr Orság, Hana Pivoňková, Jan Riedl, Michal Hocek and Miroslav Fojta
    Utilisation of enzymatic labelling with 4-aminophtalimide and 4-hydroxybenzylideneimidazolinone fluorescent derivates for monitoring of DNA-protein interaction
    Symposium Series 2014, Vol. 14, pp. 340–341 [Abstract]
    Published online 2015-07-06 23:07:27
  • Petra Ménová and Michal Hocek
    Preparation of modified oligonucleotides by nicking enzyme amplification reaction
    Symposium Series 2014, Vol. 14, pp. 324–325 [Abstract]
    Published online 2015-07-06 23:06:55
  • Michaela Mačková and Michal Hocek
    Vinyl-modified DNA and its cleavage by restriction endonucleases
    Symposium Series 2014, Vol. 14, pp. 318–319 [Abstract]
    Published online 2015-07-06 23:06:39
  • Pavel Kielkowski and Michal Hocek
    Competitive incorporations of modified versus natural nucleotides by DNA polymerases
    Symposium Series 2014, Vol. 14, pp. 295–296 [Abstract]
    Published online 2015-07-06 23:05:36
  • Miroslav Fojta, Aleš Daňhel, Petra Horáková, Medard Plucnara, Hana Pivoňková, Luděk Havran, Pavlína Vidláková, Veronika Raindlová, Jana Balintová, Hana Macíčková-Cahová and Michal Hocek
    Electrochemical analysis of DNA using switchable redox moieties
    Symposium Series 2014, Vol. 14, pp. 264–266 [Abstract]
    Published online 2015-07-06 23:04:13
  • Jitka Daďová, Petr Orság, Radek Pohl, Marie Brázdová, Miroslav Fojta and Michal Hocek
    Study of DNA-protein interactions by cross-link formation using aqueous Michael addition
    Symposium Series 2014, Vol. 14, pp. 240–241 [Abstract]
    Published online 2015-07-06 23:03:09
  • Jana Balintová, Marie Brázdová, Luděk Havran, Miroslav Fojta and Michal Hocek
    Redox labeling and redox coding of nucleic acids
    Symposium Series 2014, Vol. 14, pp. 229–230 [Abstract]
    Published online 2015-07-06 23:02:33
  • Jana Balintová, Jitka Daďová, Pavel Kielkowski, Petra Ménová, Zuzana Vaníková, Jan Riedl, Veronika Raindlová, Miroslav Fojta and Michal Hocek
    Polymerase synthesis of base-modified DNA: new methods and new applications
    Symposium Series 2014, Vol. 14, pp. 66–67 [Abstract]
    Published online 2015-07-06 22:57:12
  • Petr Nauš, Pavla Perlíková, Radek Pohl and Michal Hocek*
    Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides
    2011, Vol. 76, Issue 8, pp. 957–988 [Abstract]
  • Zbyněk Hasník, Radek Pohl, Blanka Klepetářová and Michal Hocek*
    Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines
    2009, Vol. 74, Issue 7-8, pp. 1035–1059 [Abstract] [Full text pdf]
  • Michal Hocek*, Peter Šilhár and Radek Pohl
    Cytostatic and Antiviral 6-Arylpurine Ribonucleosides VIII. Synthesis and Evaluation of 6-Substituted Purine 3'-Deoxyribonucleosides
    2006, Vol. 71, Issue 10, pp. 1484–1496 [Abstract]
  • Peter Šilhár, Radek Pohl, Ivan Votruba, Blanka Klepetářová and Michal Hocek*
    Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides
    2006, Vol. 71, Issue 6, pp. 788–803 [Abstract]
  • Peter Šilhár, Radek Pohl, Ivan Votruba and Michal Hocek*
    Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides
    2005, Vol. 70, Issue 10, pp. 1669–1695 [Abstract]
  • Pavel Turek, Martin Kotora*, Michal Hocek* and Ivan Votruba
    Novel Method for Preparation of Highly Substituted 6-Arylpurines by Reactions of 6-Alkynylpurines with Zirconacyclopentadienes
    2005, Vol. 70, Issue 3, pp. 339–349 [Abstract]
  • Petr Nauš, Ivan Votruba and Michal Hocek*
    Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides
    2004, Vol. 69, Issue 10, pp. 1955–1970 [Abstract]
  • Michal Hocek*, Dana Hocková and Jan Štambaský
    Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides
    2003, Vol. 68, Issue 5, pp. 837–848 [Abstract]
  • Michal Hocek*, Hana Dvořáková and Ivana Císařová
    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
    2002, Vol. 67, Issue 10, pp. 1560–1578 [Abstract]
  • Michal Hocek*, Irena G. Stará, Ivo Starý and Hana Dvořáková
    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
    2002, Vol. 67, Issue 8, pp. 1223–1235 [Abstract]
  • Michal Hocek*, Antonín Holý and Hana Dvořáková
    Cytostatic 6-Arylpurine Nucleosides IV. Synthesis of 2-Substituted 6-Phenylpurine Ribonucleosides
    2002, Vol. 67, Issue 3, pp. 325–335 [Abstract]
  • Michal Hocek*, Antonín Holý, Ivan Votruba and Hana Dvořáková
    Cytostatic 6-Arylpurine Nucleosides III. Synthesis and Structure-Activity Relationship Study in Cytostatic Activity of 6-Aryl-, 6-Hetaryl- and 6-Benzylpurine Ribonucleosides
    2001, Vol. 66, Issue 3, pp. 483–499 [Abstract]
  • Michal Hocek*, Antonín Holý, Ivan Votruba and Hana Dvořáková
    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
    2000, Vol. 65, Issue 11, pp. 1683–1697 [Abstract]
  • Michal Česnek, Michal Hocek* and Antonín Holý
    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
    2000, Vol. 65, Issue 8, pp. 1357–1373 [Abstract]
  • Michal Hocek* and Antonín Holý
    Perfluoroalkylation of 6-Iodopurines by Trimethyl(perfluoroalkyl)silanes. Synthesis of 6-(Perfluoroalkyl)purine Bases, Nucleosides and Acyclic Nucleotide Analogues
    1999, Vol. 64, Issue 2, pp. 229–241 [Abstract]
  • Michal Hocek, Milena Masojídková and Antonín Holý
    Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents
    1997, Vol. 62, Issue 1, pp. 136–146 [Abstract]
  • Michal Hocek and Antonín Holý
    Acyclic nucleotide analogues derived from 6-(1-aminoalkyl)purines
    1996, Vol. 61, Special Issue, pp. S55–S58 [Abstract]
  • Michal Hocek, Milena Masojídková, Antonín Holý, Graciela Andrei, Robert Snoeck, Jan Balzarini and Erik De Clercq
    Synthesis and Antiviral Activity of Acyclic Nucleotide Analogues Derived from 6-(Aminomethyl)purines and Purine-6-carboxamidines
    1996, Vol. 61, Issue 10, pp. 1525–1537 [Abstract]
  • Michal Hocek and Antonín Holý
    A Facile Synthesis of 6-Cyanopurine Bases
    1995, Vol. 60, Issue 8, pp. 1386–1389 [Abstract]
  • Michal Hocek, Milena Masojídková and Antonín Holý
    Synthesis of Acyclic Nucleotide Analogues Derived from 2-(Aminomethyl)adenine and 2-(Aminomethyl)hypoxanthine
    1995, Vol. 60, Issue 5, pp. 875–882 [Abstract]
  • Stanislav Böhm, Michal Hocek, Jan Němeček, Vladimír Havlíček and Josef Kuthan
    Preparation and Spectroscopic Properties of Spirocyclic 1-Methyl-2,4,4,6-tetraaryl-1,4-dihydropyridines
    1994, Vol. 59, Issue 5, pp. 1105–1114 [Abstract]
  • Stanislav Böhm, Michal Hocek, Stanislav Nešpůrek and Josef Kuthan
    Photocolouration of 2,4,4,6-Tetraaryl-1,4-dihydropyridines: A Semiempirical Quantum Chemical Study
    1994, Vol. 59, Issue 2, pp. 262–272 [Abstract]