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Carbocyclic analogues of nucleosides containing substituted bicyclic systems.
Šála, Michal ; Hřebabecký, Hubert (advisor) ; Černý, Miloslav (referee) ; Moravcová, Jitka (referee)
Charles University in Prague Faculty of Science Department of Organic and Nuclear Chemistry Carbocyclic analogues of nucleosides containing substituted bicyclic systems Michal Šála Ph.D. Thesis Abstract Prague 2010 Introduction Nucleoside and nucleotide analogues are of fundamental importance for all organisms. Therefore, nucleoside analogues are interesting target for drug discovery and development, mainly as potential antiviral and antitumor agents. A crucial disadvantage of natural nucleosides analogues is cleavage of the N-glycosidic bond by phosphorylases. Modification which increases resistance against enzymatic degradation is substitution of the sugar moiety furanose ring by a hydrocarbon ring. Many of such modified analogues - carbocyclic nucleosides1 - exhibit interesting antiviral activity. Several analogues containing conformationally locked bicyclic systems were also synthesized. Well known are carbocylic nucleosides with a fused cyclopropane moiety2 (bicyclo[3.1.0]hexane). Recently, novel conformationally locked carbocyclic nucleosides based on 2-oxabicyclo[2.2.1]heptane ring system were described3 (as precursors for carbocyclic locked nucleic acids). This thesis concerns the synthesis of biologically active compounds related to the carbocyclic nucleoside analogues. First part of the work is...
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Carbocyclic analogues of nucleosides containing substituted bicyclic systems.
Šála, Michal ; Hřebabecký, Hubert (advisor) ; Černý, Miloslav (referee) ; Moravcová, Jitka (referee)
Charles University in Prague Faculty of Science Department of Organic and Nuclear Chemistry Carbocyclic analogues of nucleosides containing substituted bicyclic systems Michal Šála Ph.D. Thesis Abstract Prague 2010 Introduction Nucleoside and nucleotide analogues are of fundamental importance for all organisms. Therefore, nucleoside analogues are interesting target for drug discovery and development, mainly as potential antiviral and antitumor agents. A crucial disadvantage of natural nucleosides analogues is cleavage of the N-glycosidic bond by phosphorylases. Modification which increases resistance against enzymatic degradation is substitution of the sugar moiety furanose ring by a hydrocarbon ring. Many of such modified analogues - carbocyclic nucleosides1 - exhibit interesting antiviral activity. Several analogues containing conformationally locked bicyclic systems were also synthesized. Well known are carbocylic nucleosides with a fused cyclopropane moiety2 (bicyclo[3.1.0]hexane). Recently, novel conformationally locked carbocyclic nucleosides based on 2-oxabicyclo[2.2.1]heptane ring system were described3 (as precursors for carbocyclic locked nucleic acids). This thesis concerns the synthesis of biologically active compounds related to the carbocyclic nucleoside analogues. First part of the work is...
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Novel conformationally locked nucleosides and nucleotides based on bicyclo[3.2.1]octane scaffold as a pseudosugar moiety
Šála, Michal ; Dejmek, Milan ; Procházková, Eliška ; Hřebabecký, Hubert ; Rybáček, Jiří ; Dračínský, Martin ; Novák, Pavel ; Rosenbergová, Šárka ; Fukal, J. ; Sychrovský, Vladimír ; Rosenberg, Ivan ; Nencka, Radim
A route to a series of novel carbocyclic nucleosides locked in North conformation with bicyclo[3.2.1]octane scaffold was developed. Prepared nucleosides served as a starting material for the synthesis of modified oligomers [d(GCATATCAC), r(GCAUAUCAC), and A9]. Biological effects of the prepared nucleosides as well as the hybridization properties of the appropriate duplexes were evaluated.
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The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination of purines and pyrimidines
Čechová, Lucie ; Jansa, Petr ; Šála, Michal ; Dračínský, Martin ; Holý, Antonín ; Janeba, Zlatko
The microwave-assisted decomposition of DMF was thoroughly studied and the reaction conditions (temperature, solvent effect, and effect of additives such as acids, bases, and salts) were optimized for its use in the amination reactions of various purines and pyrimidines.
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