National Repository of Grey Literature 37 records found  previous8 - 17nextend  jump to record: Search took 0.02 seconds. 
Polymerase synthesis of modified DNA containing cytosine in major groove
Kielkowski, Pavel ; Hocek, Michal
(Cytosine-5-yl)ethynyl derivatives of pyrimidine and 7-deazaadenine 2-deoxyribonucleosides and nucleoside triphosphates (dNTPs) were prepared by aqueous Sonogashira coupling. All modified dNTPs were excellent substrates for DNA polymerases to give DNA bearing acetylene- linked cytosine(s) in the major groove.
Synthesis of nucleotides bearing oligopyridine ligands and their incorporation into DNA
Kalachová, Lubica ; Hocek, Michal
The synthesis of 7-deaza-dATPs and dCTPs bearing bipyridine or terpyridine ligands via acetylene tethers was accomplished through Pd-catalyzed cross-coupling reactions. Different DNA polymerases were used for their incorporation into DNA.
Nucleosides containing 8-aza-7,9-dedeazaxanthine
Mařák, David ; Otmar, Miroslav ; Dračínský, Martin ; Krečmerová, Marcela
8-aza-7,9-dideazaxanthine nucleosides were prepared from 5-nitrouracil employing a Barton-Zard reaction.
Synthesis of new potential inhibitors of 5´-nucleotidases
Šimák, Ondřej ; Pachl, Petr ; Brynda, Jiří ; Rosenberg, Ivan
The work deals with the synthesis of potential inhibitors of 5´-nucleotidases. The phosphonobenzylidene ring of a phosphonate nucleotide derivative was recognized as a target for proposed synthetic modifications. Substituents selected on the basis of a docking study, mostly the electronegative ones, should be suitable for the formation of additional hydrogen bonds, and thus the increased inhibition of the enzymes.
Dichotomy in regioselectivity of Pd-catalyzed direct C-H arylation of protected uracils
Čerňová, Miroslava ; Hocek, Michal
Uracil bases and nucleosides bearing aryl groups in positions 5 or 6 are an important class of compounds and display wide range of biological activities1. In addition, arylation in position 5 is often used for labeling of nucleotides, oligonucleotides and DNA for applications in bioanalysis or chemical biology2. The 5- or 6-aryluracils can be prepared by heterocyclization or by cross-coupling reactions of halouracils with arylboronic acids or stannanes or metallated uracils with aryl halides. Direct C–H arylation of uracil is an alternative to classical cross-couplings where the preparation of reactive organometallic reagent is avoided. Recently, we have developed regioselective Pd-catalyzed and/or Cu-mediated direct C–H arylations of 1,3-dimethyluracil as a model compound for pyrimidine bases to position C-5 or C-6 3.
Modular synthesis of 5-substituted thiophene and furan C-nucleosides and their analogues
Bárta, Jan ; Hocek, Michal
A new modular and efficient methodology for the preparation of 5-substituted thiophen-2-yl and 5-substituted furan-2-yl C-nucleosides was developed. A Friedel–Crafts-type of C-glycosidation of 2-bromothiophene or 2-bromofuran with bis-toluoyl protected methyl- 2′-deoxyribofuranoside in presence of Lewis acid gave the desired bis-toluoyl protected 5-bromothiophne and 5-bromofuran C-nucleosides in good yields. They were used as key intermediates for Stille or Suzuki coupling whith (hetero)arylstannanes or boronic acids to afford a series of 5-(hetero)aryl thiophene and 5-(heteroaryl)furan C-nucleosides.
Synthesis of nucleosides and nucleoside triphosphates bearing anthraquinone substituents as redox probes and their enzymatic incorporation to DNA
Balintová, Jana ; Havran, Luděk ; Fojta, Miroslav ; Hocek, Michal
Modified 2′-deoxynucleosides and nucleoside triphosphates (dNTPs) bearing anthraquinone (AQ) via acetylene or propargylcarbamoyl linkers were prepared by single-step Sonogashira cross-coupling reactions halogenated nucleosides (7-iodo-7-deaza-2′-deoxyadenosine and 5-iodo-2′-deoxycytidine) or dNTPs with N-(2-propynyl)-anthraquinone carboxamide and 2-ethynylantraquinone. Polymerase incorporation of the AQ-labelled dNTPs into DNA has also been studied. Square-wave voltammetry of the AQ-labelled nucleosides and nucleotides showed one reversible peak at –0.5 V.
Synthesis of biaryl-substituted fluorescent nucleosides and nucleoside triphosphates and their incorporation to DNA
Riedl, Jan ; Hocek, Michal
A series of modified nucleosides bearing the fluorescent substituted biaryl labels attached to nucleobase was prepared and their luminescent properties were evaluated. The modified nucleosides show divers fluorescence from 400 to 560 nm when excited at 340 nm in water depending on structural and substitution pattern. The corresponding biaryl-substituted nucleoside triphosphates (dNTPs) were prepared analogously and used for polymerase incorporation to DNA. Applications in hybridization probes were studied.
Synthesis of PME derivatives on nucleobases with conformation locked via pyrrolidine ring
Rejman, Dominik ; Pohl, Radek
Among diverse nucleoside phosphonic acids, the acyclic phosphonate derivatives have been earlier shown to involve some exceptionally potent antiviral drugs (e.g., Cidofovir, Adefovir, and Tenofovir). This work presents the synthesis of such acyclic phosphonate nucleotides conformationally locked via pyrrolidine ring.
Hetaryl derivatives of 7-deazapurine ribonucleosides: potent cytostatic agents
Perlíková, Pavla ; Nauš, Petr ; Bourderioux, Aurelie ; Hocek, Michal
A series of novel 7-deazapurine ribonucleosides substituted with aryl and hetaryl groups has been prepared. Suzuki or Stille cross-coupling reactions with 6-chloro-7-deazapurine ribonucleosides substituted with H, F of Cl atom in position 7 were used in the key step of the synthesis. Either cross-coupling of protected ribonucleoside with appropriate (het)arylboronic acid or stannane followed by deprotection, or single-step aqueous-phase Suzuki cross-coupling reaction of unprotected 7-deazapurine ribonucleoside with boronic acid provided target (het)aryl-7-deazapurine ribonucleosides. 6-Furyl- and 6-thienyl-7-deazapurine ribonucleosides showed cytostatic effect in multiple cancer cell lines in nanomolar range. Application of cyclosaligenyl and alanyl-ester phosphoramidate prodrugs did not improved cytostatic activity of parent nucleosides.

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