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.

Basic information

Original name

New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs

Authors

MAIER, Lukáš (203 Czech Republic, belonging to the institution), Ondřej HYLSE (203 Czech Republic, belonging to the institution), Marek NEČAS (203 Czech Republic, belonging to the institution), Martin TRBUŠEK (203 Czech Republic, belonging to the institution), Mari YTRE-ARNE (578 Norway), Bjorn DALHUS (578 Norway), Magnar BJORAS (578 Norway) and Kamil PARUCH (203 Czech Republic, guarantor, belonging to the institution)

Edition

Tetrahedron Letters, 2014, 0040-4039

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 2.379

RIV identification code

RIV/00216224:14310/14:00075687

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.tetlet.2014.05.030

UT WoS

000337996900018

Keywords in English

Nucleoside analogs; Pseudoisocytidine; Diastereoselective synthesis; Glycosylases; NEIL1

Abstract

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.

Links

SRGA 771, interní kód MU

Name: Nucleoside Analogs with Targeted Biological Activity (Acronym: nuclangs)

Investor: South-Moravian Region, Incoming grants

Citovat

MAIER, Lukáš, Ondřej HYLSE, Marek NEČAS, Martin TRBUŠEK, Mari YTRE-ARNE, Bjorn DALHUS, Magnar BJORAS and Kamil PARUCH. New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs. Tetrahedron Letters. 2014, vol. 55, No 27, p. 3713-3716. ISSN 0040-4039. Available from: https://dx.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 = {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 and Kamil PARUCH. New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs. \textit{Tetrahedron Letters}. 2014, vol.~55, No~27, p.~3713-3716. ISSN~0040-4039. Available from: https://dx.doi.org/10.1016/j.tetlet.2014.05.030.

Detailed Information on Publication Record