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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F13%3A10159265%21RIV14-MSM-11310___
rdf:type
n3:Vysledek skos:Concept
rdfs:seeAlso
http://dx.doi.org/10.1002/cmdc.201300047
dcterms: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.
dcterms: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
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
skos:notation
RIV/00216208:11310/13:10159265!RIV14-MSM-11310___
n3:predkladatel
n13:orjk%3A11310
n5:aktivita
n11:I n11:P
n5:aktivity
I, P(GAP207/11/0344)
n5:cisloPeriodika
5
n5:dodaniDat
n18:2014
n5:domaciTvurceVysledku
n19:6659160
n5:druhVysledku
n12:J
n5:duvernostUdaju
n17:S
n5:entitaPredkladatele
n16:predkladatel
n5:idSjednocenehoVysledku
109477
n5:idVysledku
RIV/00216208:11310/13:10159265
n5:jazykVysledku
n10:eng
n5:klicovaSlova
nucleosides; fluorinated derivatives; cytostatics; antiviral agents; 7-deazapurines
n5:klicoveSlovo
n6:cytostatics n6:fluorinated%20derivatives n6:nucleosides n6:7-deazapurines n6:antiviral%20agents
n5:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n5:kontrolniKodProRIV
[DE1DFC314F17]
n5:nazevZdroje
ChemMedChem
n5:obor
n9:CC
n5:pocetDomacichTvurcuVysledku
1
n5:pocetTvurcuVysledku
9
n5:projekt
n20:GAP207%2F11%2F0344
n5:rokUplatneniVysledku
n18:2013
n5:svazekPeriodika
8
n5:tvurceVysledku
Ménová, Petra Raindlová, Veronika Slavětínská, Lenka Tloušťová, Eva Eberlin, Ludovic Bahador, Gina Perlíková, Pavla Hocek, Michal Lee, Yu-Jen
n5:wos
000318245300016
s:issn
1860-7179
s:numberOfPages
15
n14:doi
10.1002/cmdc.201300047
n21:organizacniJednotka
11310