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@article{1185536, author = {Maier, Lukáš and Hylse, Ondřej and Nečas, Marek and Trbušek, Martin and YtreandArne, Mari and Dalhus, Bjorn and Bjoras, Magnar and Paruch, Kamil}, article_number = {27}, doi = {http://dx.doi.org/10.1016/j.tetlet.2014.05.030}, keywords = {Nucleoside analogs; Pseudoisocytidine; Diastereoselective synthesis; Glycosylases; NEIL1}, language = {eng}, issn = {0040-4039}, journal = {Tetrahedron Letters}, title = {New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs}, volume = {55}, year = {2014} }
TY - JOUR ID - 1185536 AU - Maier, Lukáš - Hylse, Ondřej - Nečas, Marek - Trbušek, Martin - Ytre-Arne, Mari - Dalhus, Bjorn - Bjoras, Magnar - Paruch, Kamil PY - 2014 TI - New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs JF - Tetrahedron Letters VL - 55 IS - 27 SP - 3713-3716 EP - 3713-3716 SN - 00404039 KW - Nucleoside analogs KW - Pseudoisocytidine KW - Diastereoselective synthesis KW - Glycosylases KW - NEIL1 N2 - 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. ER -
MAIER, Lukáš, Ondřej HYLSE, Marek NEČAS, Martin TRBUŠEK, Mari YTRE-ARNE, Bjorn DALHUS, Magnar BJORAS a Kamil PARUCH. New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs. \textit{Tetrahedron Letters}. 2014, roč.~55, č.~27, s.~3713-3716. ISSN~0040-4039. Dostupné z: https://dx.doi.org/10.1016/j.tetlet.2014.05.030.
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