Collect. Czech. Chem. Commun. 2011, 76, 1187-1198
https://doi.org/10.1135/cccc2011105
Published online 2011-09-20 09:01:13

Efficient synthesis and biological properties of the 2′-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates

Petr Jansa*, Viktor Kolman, Alexandra Kostinová, Martin Dračínský, Helena Mertlíková-Kaiserová and Zlatko Janeba

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

Individual author index pages


Other CCCC articles of these authors

  • Zlatko Janeba and Antonín Holý
    Synthesis of 8-hydroxy and 8-mercapto derivatives of acyclic adenine nucleoside and nucleotide analogs. Alkylation of 8-substituted adenines
    Symposium Series 1999, Vol. 2, pp. 260–262 [Abstract]
    Published online 2016-05-08 23:32:05
  • David Mařák, Miroslav Otmar, Martin Dračínský, Ivan Votruba and Antonín Holý
    Nucleosides and nucleotides containing 8-aza-7,9-dideazaxanthine
    Symposium Series 2008, Vol. 10, pp. 426–428 [Abstract]
    Published online 2015-10-30 18:44:11
  • Petr Jansa, Martin Dračínský and Antonín Holý
    Efficient synthesis of "open-ring, close-ring" acyclic nucleoside phosphonates
    Symposium Series 2008, Vol. 10, pp. 360–361 [Abstract]
    Published online 2015-10-30 18:42:02
  • Martin Dračínský, Marcela Krečmerová and Antonín Holý
    Study of chemical stability of antivirally active 5-azacytosine acyclic nucleoside phosphonates using NMR spectroscopy
    Symposium Series 2008, Vol. 10, pp. 338–340 [Abstract]
    Published online 2015-10-30 18:41:11
  • Petra Doláková, Martin Dračínský and Antonín Holý
    Synthesis of acyclic nucleoside diphosphate mimics
    Symposium Series 2008, Vol. 10, pp. 336–337 [Abstract]
    Published online 2015-10-30 18:41:05
  • Ondřej Baszczyňski, Antonín Holý, Martin Dračínský and Blanka Klepetářová
    Synthesis of N9-(3-fluoro-2-phosphonomethoxypropyl) (FPMP) derivatives of N6-substituted adenines and 2,6-diaminopurines
    Symposium Series 2008, Vol. 10, pp. 315–316 [Abstract]
    Published online 2015-10-30 18:40:22
  • Radim Nencka, Hubert Hřebabecký, Ivan Votruba, Martin Dračínský and Antonín Holý
    Metalation of 6-halo-2,4-dimethoxypyrimidines as the key step for the synthesis of biologicaly active compounds
    Symposium Series 2008, Vol. 10, pp. 249–253 [Abstract]
    Published online 2015-10-30 18:38:37
  • Zlatko Janeba, Antonín Holý and Zdeněk Zídek
    Biological properties of the C-8 substituted analogues of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA)
    Symposium Series 2011, Vol. 12, pp. 344–346 [Abstract]
  • Tomáš Tichý, Graciela Andrei, Martin Dračínský, Antonín Holý, Jan Balzarini, Robert Snoeck and Marcela Krečmerová
    New amphiphilic prodrugs of adefovir and cidofovir
    Symposium Series 2011, Vol. 12, pp. 477–479 [Abstract]
    Published online 2015-08-20 10:25:04
  • Petr Jansa, Petr Špaček, Antonín Holý, Ivan Votruba and Zlatko Janeba
    Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the "click" protocol
    Symposium Series 2011, Vol. 12, pp. 467–468 [Abstract]
    Published online 2015-08-20 10:24:43
  • David Mařák, Miroslav Otmar, Martin Dračínský and Marcela Krečmerová
    Nucleosides containing 8-aza-7,9-dideazaxanthine
    Symposium Series 2011, Vol. 12, pp. 383–385 [Abstract]
    Published online 2015-08-20 10:19:50
  • Marcela Krečmerová, Antonín Holý, Dana Hocková, Martin Dračínský, Dianne T. Keough and Luke W. Guddat
    9-[2-Hydroxy-3-(phosphonomethoxy)propyl] ("iso-HPMP") derivatives of purine bases and their side-chain modified analogues: synthesis and antimalarial activity
    Symposium Series 2011, Vol. 12, pp. 381–382 [Abstract]
    Published online 2015-08-20 10:19:45
  • Soňa Kovačková, Martin Dračínský and Dominik Rejman
    Piperidine nucleoside phosphonic acid derivatives
    Symposium Series 2011, Vol. 12, pp. 372–374 [Abstract]
    Published online 2015-08-20 10:19:28
  • Petr Jansa, Viktor Kolman and Zlatko Janeba
    Synthesis and biological properties of the 2'-trifluoro-methyl analogues of tenofovir
    Symposium Series 2011, Vol. 12, pp. 370–371 [Abstract]
    Published online 2015-08-20 10:19:23
  • Petr Jansa, Antonín Holý, Martin Dračínský, Ondřej Baszczyňski, Michal Česnek and Zlatko Janeba
    The unique impact of microwave irradiaton on the chemistry of acyclic nucleoside phosphonates
    Symposium Series 2011, Vol. 12, pp. 347–348 [Abstract]
    Published online 2015-08-20 10:18:28
  • Petr Jansa, Martin Maxmilian Kaiser, Antonín Holý and Zlatko Janeba
    A novel, highly stereoselective synthetic approach for the preparation of substituted 2,5-dihydro-2,5-dihydroxyfurans
    Symposium Series 2011, Vol. 12, pp. 339–341 [Abstract]
    Published online 2015-08-20 10:13:05
  • Martin Dračínský, Petr Jansa, Jana Chocholoušová, Jaroslav Vacek, Soňa Kovačková and Antonín Holý
    The mechanism of isotopic exchange reaction of hydrogen H-5 of uracil derivatives in water and in non-protic solvents
    Symposium Series 2011, Vol. 12, pp. 323–324 [Abstract]
    Published online 2015-08-20 10:12:29
  • Lucie Čechová, Petr Jansa, Michal Šála, Martin Dračínský, Antonín Holý and Zlatko Janeba
    The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination of purines and pyrimidines
    Symposium Series 2011, Vol. 12, pp. 312–313 [Abstract]
    Published online 2015-08-20 10:12:06
  • Michal Česnek, Petra Břehová, Martin Dračínský, Antonín Holý and Zlatko Janeba
    The efficient synthesis of 2-aryl substituted pyrimidine acyclic nucleoside phosphonates using Liebeskind-Srogl cross-coupling
    Symposium Series 2011, Vol. 12, pp. 310–311 [Abstract]
    Published online 2015-08-20 10:12:01
  • Ondřej Baszczyňski, Petr Jansa, Dana Hocková, Zlatko Janeba, Martin Dračínský, Antonín Holý, Dianne T. Keough, John de Jersey and Luke W. Guddat
    3-Fluoro-2-(phosphonomethoxy)propyl hypoxanthine and guanine derivatives as inhibitors of plasmodial hypoxanthine-guanine-xanthine phosphoribosyltransferases
    Symposium Series 2011, Vol. 12, pp. 302–303 [Abstract]
    Published online 2015-08-20 10:11:43
  • Milan Dejmek, Hubert Hřebabecký, Michal Šála, Martin Dračínský and Radim Nencka
    Synthesis of conformationally locked carbocyclic nucleosides with norbornane as pseudosugar moiety
    Symposium Series 2011, Vol. 12, pp. 208–212 [Abstract]
    Published online 2015-08-20 10:01:05
  • Dana Hocková, Antonín Holý, Michal Česnek, Ondřej Baszczyňski, Tomáš Tichý, Marcela Krečmerová, Zlatko Janeba, Tina S. Skinner-Adams, Lieve Naesens, Dianne T. Keoughd, John de Jersey and Luke W. Guddat
    Acyclic nucleoside phosphonates as inhibitors of hypoxanthine-guanine-xanthine phosphoribosyltransferase: new anti-malarial chemotherapy leads
    Symposium Series 2011, Vol. 12, pp. 171–174 [Abstract]
    Published online 2015-08-20 10:00:19
  • Michal Šála, Milan Dejmek, Eliška Procházková, Hubert Hřebabecký, Jiří Rybáček, Martin Dračínský, Pavel Novák, Šárka Rosenbergová, Jiří Fukal, Vladimír Sychrovský, Ivan Rosenberg and Radim Nencka
    Novel conformationally locked nucleosides and oligonucleotides based on bicyclo[3.2.1]octane scaffold as a pseudosugar moiety
    Symposium Series 2014, Vol. 14, pp. 379–380 [Abstract]
    Published online 2015-07-06 23:09:07
  • Petr Špaček, Dianne T. Keough, Silvie Vrbková, Lenka Slavětínská, Zlatko Janeba, Lieve Naesens, Michael D. Edstein, Marina Chavchich, Tzu-Hsuan Wang, John de Jersey, Luke W. Guddat and Dana Hocková
    Acyclic nucleoside bis-phosphonates as potent inhibitors of 6-oxopurine phosphoribosyltransferases
    Symposium Series 2014, Vol. 14, pp. 375–376 [Abstract]
    Published online 2015-07-06 23:08:54
  • Eliška Procházková, Hubert Hřebabecký, Radim Nencka and Martin Dračínský
    Enzymatic decomposition of a locked nucleoside phosphoramidate monitored by 31P NMR spectroscopy
    Symposium Series 2014, Vol. 14, pp. 356–357 [Abstract]
    Published online 2015-07-06 23:08:13
  • Martin Maxmilian Kaiser, Pavel Novák, Šárka Rosenbergová, Lenka Poštová-Slavětínská, Ivan Rosenberg and Zlatko Janeba
    Oligonucleotides modified with acyclic nucleoside phosphonate (HPEP) units
    Symposium Series 2014, Vol. 14, pp. 293–294 [Abstract]
    Published online 2015-07-06 23:05:30
  • Zlatko Janeba, Lucie Čechová, Jiří Žurek, Eliška Procházková and Martin Dračínský
    Synthesis and biological properties of polysubstituted 5-nitrosopyrimidines
    Symposium Series 2014, Vol. 14, pp. 285–286 [Abstract]
    Published online 2015-07-06 23:05:07
  • Eliška Procházková, Lucie Čechová, Jiří Žurek, Zlatko Janeba and Martin Dračínský
    Switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines
    Symposium Series 2014, Vol. 14, pp. 251–254 [Abstract]
    Published online 2015-07-06 23:03:40
  • Dana Hocková, Dianne T. Keough, Petr Špaček, Zlatko Janeba, Michael D. Edstein, Marina Chavchich, Tzu-Hsuan Wang, Wai Soon Eng, Nicholas P. West, John de Jersey and Luke W. Guddat
    Acyclic nucleoside bisphosphonates as inhibitors of 6-oxopurine phosphoribosyltransferases: potential antimalarial and antibacterial agents
    Symposium Series 2014, Vol. 14, pp. 107–110 [Abstract]
    Published online 2015-07-06 22:58:24
  • Martin Dračínský*, Petr Jansa* and Tomáš Elbert
    Isotope exchange reactions of the hydrogen H-5 of selected pyrimidine derivatives and the preparation of tritium-labeled pyrimidines
    2011, Vol. 76, Issue 12, pp. 1567–1577 [Abstract]
  • Milan Dejmek, Hubert Hřebabecký, Martin Dračínský, Johan Neyts, Pieter Leyssen, Helena Mertlíková-Kaiserová and Radim Nencka*
    Conformationally locked nucleoside analogues based on the bridgehead substituted 7-oxonorbornane and their antiviral properties
    2011, Vol. 76, Issue 12, pp. 1549–1566 [Abstract]
  • Petr Jansa*, Petr Špaček, Ivan Votruba, Petra Břehová, Martin Dračínský, Blanka Klepetářová and Zlatko Janeba
    Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the “click” protocol
    2011, Vol. 76, Issue 9, pp. 1121–1131 [Abstract]
  • Radim Nencka, Hubert Hřebabecký* and Martin Dračínský
    Model synthesis of six-membered carbocyclic spironucleosides
    2010, Vol. 75, Issue 12, pp. 1259–1272 [Abstract]
  • Zlatko Janeba*, Milena Masojídková and Antonín Holý
    Alternative synthesis of 9-{3-[(diisopropoxyphosphoryl)methoxy]-2-hydroxypropyl}adenine and its free phosphonates substituted at the C-8 position of purine base
    2010, Vol. 75, Issue 3, pp. 371–381 [Abstract]
  • Michal Šála, Hubert Hřebabecký*, Martin Dračínský, Milena Masojídková, Armando M. De Palma, Johan Neyts and Antonín Holý
    Synthesis of novel racemic carbocyclic nucleosides derived from 5,6-disubstituted norbornene
    2010, Vol. 75, Issue 1, pp. 1–20 [Abstract]
  • Hubert Hřebabecký*, Martin Dračínský and Antonín Holý
    New carbocyclic nucleoside analogues built on a bicyclo[2.2.2]octane-2,2-dimethanol template
    2009, Vol. 74, Issue 9, pp. 1425–1441 [Abstract]
  • Hubert Hřebabecký*, Martin Dračínský, Armando M. De Palma, Johan Neyts and Antonín Holý
    Synthesis of novel carbocyclic nucleoside analogues derived from 7-oxabicyclo[2.2.1]heptane-2-methanol
    2009, Vol. 74, Issue 3, pp. 487–502 [Abstract]
  • Hubert Hřebabecký*, Martin Dračínský, Armando M. De Palma, Johan Neyts and Antonín Holý
    Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses
    2009, Vol. 74, Issue 3, pp. 469–485 [Abstract]
  • Hubert Hřebabecký*, Martin Dračínský and Antonín Holý
    Synthesis of Novel Carbocyclic Nucleoside Analogues Containing Bicyclo[2.2.1]hept-2-ene-2-methanol
    2008, Vol. 73, Issue 1, pp. 44–58 [Abstract]
  • Milan Dejmek, Hubert Hřebabecký*, Martin Dračínský and Antonín Holý
    Synthesis of Novel Carbocyclic Nucleoside Analogues Derived from 2-(Hydroxymethyl)bicyclo[2.2.1]heptane
    2007, Vol. 72, Issue 11, pp. 1523–1544 [Abstract]
  • Hubert Hřebabecký*, Martin Dračínský and Antonín Holý
    Synthesis of Novel Carbocyclic Nucleosides and Pro-Tides Derived from 4-Oxatricyclo[4.2.1.03,7]nonane-9-methanol
    2007, Vol. 72, Issue 10, pp. 1331–1349 [Abstract]
  • Silvie Vrbková*, Martin Dračínský and Antonín Holý
    Bifunctional Acyclic Nucleoside Phosphonates: 2. Symmetrical 2-{[Bis(phosphono)methoxy]methyl}ethyl Derivatives of Purines and Pyrimidines
    2007, Vol. 72, Issue 7, pp. 965–983 [Abstract]
  • Martina Džoganová, Miloslav Černý, Miloš Buděšínský*, Martin Dračínský and Tomáš Trnka
    Epoxide Migration and Pseudo-Epoxide Migration of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses. Synthesis of Some Deoxy Halo Derivatives of 1,6-Anhydro-β-D-hexopyranoses
    2006, Vol. 71, Issue 10, pp. 1497–1515 [Abstract]
  • Jitka Poljaková, Martin Dračínský, Eva Frei, Jiří Hudeček and Marie Stiborová*
    The Effect of pH on Peroxidase-Mediated Oxidation of and DNA Adduct Formation by Ellipticine
    2006, Vol. 71, Issue 8, pp. 1169–1185 [Abstract]
  • Martin Dračínský, Simona Hybelbauerová, Jan Sejbal and Miloš Buděšínský*
    Preparation and Conformational Study of B-Ring Substituted Lupane Derivatives
    2006, Vol. 71, Issue 8, pp. 1131–1160 [Abstract]
  • Hubert Hřebabecký*, Milena Masojídková, Martin Dračínský and Antonín Holý
    Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol
    2006, Vol. 71, Issue 6, pp. 871–888 [Abstract]
  • Martin Dračínský, Václav Richtr, Václav Křeček, Jan Sejbal, Jiří Klinot and Miloš Buděšínský*
    Preparation and Conformational Study of 19β,28-Epoxy-18α-olean-5-ene Derivatives
    2006, Vol. 71, Issue 3, pp. 387–410 [Abstract]
  • Zlatko Janeba*, Antonín Holý and Milena Masojídková
    Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives
    2001, Vol. 66, Issue 9, pp. 1393–1406 [Abstract]
  • Zlatko Janeba*, Antonín Holý and Milena Masojídková
    Synthesis of 8-Amino- and N-Substituted 8-Aminoadenine Derivatives of Acyclic Nucleoside and Nucleotide Analogs
    2001, Vol. 66, Issue 3, pp. 517–532 [Abstract]
  • Zlatko Janeba*, Antonín Holý and Milena Masojídková
    Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine
    2000, Vol. 65, Issue 11, pp. 1698–1712 [Abstract]
  • Zlatko Janeba*, Antonín Holý and Milena Masojídková
    Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-one
    2000, Vol. 65, Issue 7, pp. 1126–1144 [Abstract]
  • Zlatko Janeba and Antonín Holý
    Intramolecular cyclization of some (S)-9-(3-hydroxy-2-phosphonomethoxypropyl)adenine derivatives
    1996, Vol. 61, Special Issue, pp. S116–S117 [Abstract]
  • Zlatko Janeba, Antonín Holý, Hana Votavová and Milena Masojídková
    Intramolecular Cyclization of Some Acyclic Nucleoside Analogs
    1996, Vol. 61, Issue 3, pp. 442–457 [Abstract]