Diastereoselective Flexible Synthesis of Carbocyclic C
Nucleosides

J 2017

Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides

MAIER, Lukáš, PrashantKumar KHIRSARIYA, Ondřej HYLSE, Santosh Kumar ADLA, Lenka ČERNOVÁ et. al.

Basic information

Original name

Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides

Authors

MAIER, Lukáš (203 Czech Republic, belonging to the institution), PrashantKumar KHIRSARIYA (356 India, belonging to the institution), Ondřej HYLSE (203 Czech Republic, belonging to the institution), Santosh Kumar ADLA (356 India, belonging to the institution), Lenka ČERNOVÁ (703 Slovakia, belonging to the institution), Michal POLJAK (703 Slovakia, belonging to the institution), Soňa KRAJČOVIČOVÁ (703 Slovakia, belonging to the institution), Erik WEIS (703 Slovakia), Stanislav DRÁPELA (203 Czech Republic), Karel SOUČEK (203 Czech Republic) and Kamil PARUCH (203 Czech Republic, guarantor, belonging to the institution)

Edition

The Journal of Organic Chemistry, WASHINGTON, DC USA, American Chemical Society, 2017, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

přístup k publikaci

Impact factor

Impact factor: 4.805

RIV identification code

RIV/00216224:14310/17:00096895

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.6b02594

UT WoS

000398986000004

Keywords in English

POLYHYDROXYLATED N-ALKOXYPIPERIDINES; CHEMICAL-STABILITY; ANTITUMOR-ACTIVITY; ANALOGS; DERIVATIVES; MITSUNOBU; CATALYSIS; ALCOHOLS

Abstract

V originále

Carbocyclic C nucleosides are quite rare. Our route enables flexible preparation of three classes of these nucleoside analogs from common precursors properly substituted cyclopentanones, which can be prepared racemic (in six steps) or optically pure (in ten steps) from inexpensive norbornadiene. The methodology allows flexible manipulation of individual positions around the cyclopentane ring, namely highly diastereoselective installation of carbo- and heterocyclic substituents at position 1, orthogonal functionalization of position 5, and efficient inversion of stereochemistry at position 2. Newly prepared carbocyclic C analog of tubercidine, profiled in MCF7 (breast cancer) and HFF1 (human foreskin fibroblasts) cell cultures, is less potent than tubercidine itself, but more selectively toxic toward the tumorigenic cells.

Links

LM2015043, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

LM2015063, research and development project

Name: Národní infrastruktura chemické biologie (Acronym: CZ-OPENSCREEN)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

MAIER, Lukáš, PrashantKumar KHIRSARIYA, Ondřej HYLSE, Santosh Kumar ADLA, Lenka ČERNOVÁ, Michal POLJAK, Soňa KRAJČOVIČOVÁ, Erik WEIS, Stanislav DRÁPELA, Karel SOUČEK and Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. The Journal of Organic Chemistry. WASHINGTON, DC USA: American Chemical Society, 2017, vol. 82, No 7, p. 3382-3402. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b02594.

@article{1382487,
   author = {Maier, Lukáš and Khirsariya, PrashantKumar and Hylse, Ondřej and Adla, Santosh Kumar and Černová, Lenka and Poljak, Michal and Krajčovičová, Soňa and Weis, Erik and Drápela, Stanislav and Souček, Karel and Paruch, Kamil},
   article_location = {WASHINGTON, DC USA},
   article_number = {7},
   doi = {http://dx.doi.org/10.1021/acs.joc.6b02594},
   keywords = {POLYHYDROXYLATED N-ALKOXYPIPERIDINES; CHEMICAL-STABILITY; ANTITUMOR-ACTIVITY; ANALOGS; DERIVATIVES; MITSUNOBU; CATALYSIS; ALCOHOLS},
   language = {eng},
   issn = {0022-3263},
   journal = {The Journal of Organic Chemistry},
   title = {Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides},
   url = {http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02594},
   volume = {82},
   year = {2017}
}

TY  - JOUR
ID  - 1382487
AU  - Maier, Lukáš - Khirsariya, PrashantKumar - Hylse, Ondřej - Adla, Santosh Kumar - Černová, Lenka - Poljak, Michal - Krajčovičová, Soňa - Weis, Erik - Drápela, Stanislav - Souček, Karel - Paruch, Kamil
PY  - 2017
TI  - Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides
JF  - The Journal of Organic Chemistry
VL  - 82
IS  - 7
SP  - 3382-3402
EP  - 3382-3402
PB  - American Chemical Society
SN  - 00223263
KW  - POLYHYDROXYLATED N-ALKOXYPIPERIDINES
KW  - CHEMICAL-STABILITY
KW  - ANTITUMOR-ACTIVITY
KW  - ANALOGS
KW  - DERIVATIVES
KW  - MITSUNOBU
KW  - CATALYSIS
KW  - ALCOHOLS
UR  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02594
L2  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02594
N2  - Carbocyclic C nucleosides are quite rare. Our route enables flexible preparation of three classes of these nucleoside analogs from common precursors properly substituted cyclopentanones, which can be prepared racemic (in six steps) or optically pure (in ten steps) from inexpensive norbornadiene. The methodology allows flexible manipulation of individual positions around the cyclopentane ring, namely highly diastereoselective installation of carbo- and heterocyclic substituents at position 1, orthogonal functionalization of position 5, and efficient inversion of stereochemistry at position 2. Newly prepared carbocyclic C analog of tubercidine, profiled in MCF7 (breast cancer) and HFF1 (human foreskin fibroblasts) cell cultures, is less potent than tubercidine itself, but more selectively toxic toward the tumorigenic cells.
ER  -

MAIER, Lukáš, PrashantKumar KHIRSARIYA, Ondřej HYLSE, Santosh Kumar ADLA, Lenka ČERNOVÁ, Michal POLJAK, Soňa KRAJČOVIČOVÁ, Erik WEIS, Stanislav DRÁPELA, Karel SOUČEK and Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. \textit{The Journal of Organic Chemistry}. WASHINGTON, DC USA: American Chemical Society, 2017, vol.~82, No~7, p.~3382-3402. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b02594.

Detailed Information on Publication Record