New carbocyclic nucleosides: synthesis of carbocyclic
pseudoisocytidine and its analogs

J 2014

New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs

MAIER, Lukáš; Ondřej HYLSE; Marek NEČAS; Martin TRBUŠEK; Mari YTRE-ARNE et al.

Základní údaje

Originální název

New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs

Autoři

MAIER, Lukáš; Ondřej HYLSE; Marek NEČAS; Martin TRBUŠEK; Mari YTRE-ARNE; Bjorn DALHUS; Magnar BJORAS a Kamil PARUCH

Vydání

Tetrahedron Letters, 2014, 0040-4039

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 2.379

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/14:00075687

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

Nucleoside analogs; Pseudoisocytidine; Diastereoselective synthesis; Glycosylases; NEIL1

Štítky

AKR, rivok

Změněno: 13. 3. 2018 10:20, doc. Mgr. Marek Nečas, Ph.D.

Anotace

V originále

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.

Návaznosti

SRGA 771, interní kód MU

Název: Nucleoside Analogs with Targeted Biological Activity (Akronym: nuclangs)

Investor: Jihomoravský kraj, Nucleoside Analogs with Targeted Biological Activity, Reintegrační granty

Citovat

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. Tetrahedron Letters. 2014, roč. 55, č. 27, s. 3713-3716. ISSN 0040-4039. Dostupné z: https://doi.org/10.1016/j.tetlet.2014.05.030.

@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 = {https://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://doi.org/10.1016/j.tetlet.2014.05.030.

Přehled o publikaci