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Description
| - A series of sugar-modified derivatives of cytostatic 7-heteroaryl-7-deazaadenosines (2-deoxy-2-fluororibo- and 2-deoxy-2,2-difluororibonucleosides) bearing an aryl or heteroaryl group at position7 was prepared and screened for biological activity. The difluororibonucleosides were prepared by non- stereoselective glycosidation of 6-chloro-7-deazapurine with benzoyl-protected 2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl-1-mesylate, followed by amination and aqueous Suzuki cross-couplings with (het)arylboronic acids. The fluororibo derivatives were prepared by aqueous palladium-catalyzed cross-coupling reactions of the corresponding 7-iodo-7-deazaadenine 2-deoxy-2-fluororibonucleoside 20 with (het)arylboronic acids. The key intermediate 20 was prepared by a six-step sequence from the corresponding arabinonucleoside by selective protection of 3- and 5-hydroxy groups with acid-labile groups, followed by stereoselective SN2 fluorination and deprotection. Some of the title nucleosides and 7-iodo-7-deazaadenine intermediates showed micromolar cytostatic or anti-HCV activity. The most active were 7-iodo and 7-ethynyl derivatives. The corresponding 2-deoxy-2,2-difluororibonucleoside 5-O-triphosphates were found to be good substrates for bacterial DNA polymerases, but are inhibitors of human polymerase.
- A series of sugar-modified derivatives of cytostatic 7-heteroaryl-7-deazaadenosines (2-deoxy-2-fluororibo- and 2-deoxy-2,2-difluororibonucleosides) bearing an aryl or heteroaryl group at position7 was prepared and screened for biological activity. The difluororibonucleosides were prepared by non- stereoselective glycosidation of 6-chloro-7-deazapurine with benzoyl-protected 2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl-1-mesylate, followed by amination and aqueous Suzuki cross-couplings with (het)arylboronic acids. The fluororibo derivatives were prepared by aqueous palladium-catalyzed cross-coupling reactions of the corresponding 7-iodo-7-deazaadenine 2-deoxy-2-fluororibonucleoside 20 with (het)arylboronic acids. The key intermediate 20 was prepared by a six-step sequence from the corresponding arabinonucleoside by selective protection of 3- and 5-hydroxy groups with acid-labile groups, followed by stereoselective SN2 fluorination and deprotection. Some of the title nucleosides and 7-iodo-7-deazaadenine intermediates showed micromolar cytostatic or anti-HCV activity. The most active were 7-iodo and 7-ethynyl derivatives. The corresponding 2-deoxy-2,2-difluororibonucleoside 5-O-triphosphates were found to be good substrates for bacterial DNA polymerases, but are inhibitors of human polymerase. (en)
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Title
| - Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines
- Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines (en)
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skos:prefLabel
| - Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines
- Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines (en)
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skos:notation
| - RIV/00216208:11310/13:10159265!RIV14-MSM-11310___
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http://linked.open...avai/riv/aktivita
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http://linked.open...avai/riv/aktivity
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http://linked.open...iv/cisloPeriodika
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http://linked.open...vai/riv/dodaniDat
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http://linked.open...aciTvurceVysledku
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http://linked.open.../riv/druhVysledku
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http://linked.open...iv/duvernostUdaju
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http://linked.open...titaPredkladatele
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http://linked.open...dnocenehoVysledku
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http://linked.open...ai/riv/idVysledku
| - RIV/00216208:11310/13:10159265
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http://linked.open...riv/jazykVysledku
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http://linked.open.../riv/klicovaSlova
| - nucleosides; fluorinated derivatives; cytostatics; antiviral agents; 7-deazapurines (en)
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http://linked.open.../riv/klicoveSlovo
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http://linked.open...odStatuVydavatele
| - GB - Spojené království Velké Británie a Severního Irska
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http://linked.open...ontrolniKodProRIV
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http://linked.open...i/riv/nazevZdroje
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http://linked.open...in/vavai/riv/obor
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http://linked.open...ichTvurcuVysledku
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http://linked.open...cetTvurcuVysledku
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http://linked.open...vavai/riv/projekt
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http://linked.open...UplatneniVysledku
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http://linked.open...v/svazekPeriodika
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http://linked.open...iv/tvurceVysledku
| - Hocek, Michal
- Slavětínská, Lenka
- Perlíková, Pavla
- Tloušťová, Eva
- Ménová, Petra
- Raindlová, Veronika
- Bahador, Gina
- Eberlin, Ludovic
- Lee, Yu-Jen
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http://linked.open...ain/vavai/riv/wos
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issn
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number of pages
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http://bibframe.org/vocab/doi
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http://localhost/t...ganizacniJednotka
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