About: New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs

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About: New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Cyclopentane-containing nucleoside analogs with a CAC connection between the (heterocyclic) base and the carbocyclic scaffold are quite rare. Herein, we report the synthesis of previously unknown racemic carbocyclic pseudoisocytidine and its analogs, which were prepared in 13 steps from commercially availavailable materials. Pseudoisocytidine and its sulfur analog were moderately active against the mantle celllymphoma cell line, JVM-3. We also prepared a versatile cyclopentanone intermediate, which can be converted into novel carbocyclic nucleosides via highly stereoselective addition of organometallic nucleophiles; the adduct with phenyllithium, the stereochemistry of which was unambiguously confirmed by X-ray crystallography, inhibits glycosylase NEIL1 in a dose-dependent manner. Cyclopentane-containing nucleoside analogs with a CAC connection between the (heterocyclic) base and the carbocyclic scaffold are quite rare. Herein, we report the synthesis of previously unknown racemic carbocyclic pseudoisocytidine and its analogs, which were prepared in 13 steps from commercially availavailable materials. Pseudoisocytidine and its sulfur analog were moderately active against the mantle celllymphoma cell line, JVM-3. We also prepared a versatile cyclopentanone intermediate, which can be converted into novel carbocyclic nucleosides via highly stereoselective addition of organometallic nucleophiles; the adduct with phenyllithium, the stereochemistry of which was unambiguously confirmed by X-ray crystallography, inhibits glycosylase NEIL1 in a dose-dependent manner. (en)
Title	New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs (en)
skos:prefLabel	New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs (en)
skos:notation	RIV/00216224:14310/14:00075687!RIV15-MSM-14310___
http://linked.open...avai/riv/aktivita	R
http://linked.open...avai/riv/aktivity	R
http://linked.open...iv/cisloPeriodika	27
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Paruch, Kamil Maier, Lukáš Nečas, Marek Trbušek, Martin Hylse, Ondřej
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Masarykova univerzita / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	32345
http://linked.open...ai/riv/idVysledku	RIV/00216224:14310/14:00075687
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Nucleoside analogs; Pseudoisocytidine; Diastereoselective synthesis; Glycosylases; NEIL1 (en)
http://linked.open.../riv/klicoveSlovo	Nucleoside analogs Diastereoselective synthesis Glycosylases NEIL1 Pseudoisocytidine
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[EEFC96F27C6D]
http://linked.open...i/riv/nazevZdroje	Tetrahedron Letters
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	55
http://linked.open...iv/tvurceVysledku	Nečas, Marek Paruch, Kamil Trbušek, Martin Maier, Lukáš Bjoras, Magnar Dalhus, Bjorn Hylse, Ondřej Ytre-Arne, Mari
http://linked.open...ain/vavai/riv/wos	000337996900018
issn	0040-4039
number of pages	4 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.tetlet.2014.05.030
http://localhost/t...ganizacniJednotka	14310

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