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.

Základní údaje

Originální název

Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides

Autoři

MAIER, Lukáš (203 Česká republika, domácí), PrashantKumar KHIRSARIYA (356 Indie, domácí), Ondřej HYLSE (203 Česká republika, domácí), Santosh Kumar ADLA (356 Indie, domácí), Lenka ČERNOVÁ (703 Slovensko, domácí), Michal POLJAK (703 Slovensko, domácí), Soňa KRAJČOVIČOVÁ (703 Slovensko, domácí), Erik WEIS (703 Slovensko), Stanislav DRÁPELA (203 Česká republika), Karel SOUČEK (203 Česká republika) a Kamil PARUCH (203 Česká republika, garant, domácí)

Vydání

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

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

přístup k publikaci

Impakt faktor

Impact factor: 4.805

Kód RIV

RIV/00216224:14310/17:00096895

Organizační jednotka

Přírodovědecká fakulta

DOI

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

UT WoS

000398986000004

Klíčová slova anglicky

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

Štítky

NZ, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 1. 4. 2018 09:30, Ing. Nicole Zrilić

Anotace

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.

Návaznosti

LM2015043, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

LM2015063, projekt VaV

Název: Národní infrastruktura chemické biologie (Akronym: CZ-OPENSCREEN)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CZ-OPENSCREEN: National Infrastructure for Chemical Biology

Citovat

MAIER, Lukáš, PrashantKumar KHIRSARIYA, Ondřej HYLSE, Santosh Kumar ADLA, Lenka ČERNOVÁ, Michal POLJAK, Soňa KRAJČOVIČOVÁ, Erik WEIS, Stanislav DRÁPELA, Karel SOUČEK a Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. The Journal of Organic Chemistry. WASHINGTON, DC USA: American Chemical Society, 2017, roč. 82, č. 7, s. 3382-3402. ISSN 0022-3263. Dostupné z: 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 a Kamil PARUCH. Diastereoselective Flexible Synthesis of Carbocyclic C Nucleosides. \textit{The Journal of Organic Chemistry}. WASHINGTON, DC USA: American Chemical Society, 2017, roč.~82, č.~7, s.~3382-3402. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.6b02594.

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