Synthesis and in Vitro Cytotoxicity of Acetylated 3-Fluoro,4-Fluoro and 3,4-Difluoro Analogs of D-glucosamine and D-galactosamine.

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F16%3A00458825" target="_blank" >RIV/67985858:_____/16:00458825 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/16:00458825 RIV/00209805:_____/16:N0000027 RIV/00216208:11310/16:10324341

Výsledek na webu

<a href="http://dx.doi.org/10.3762/bjoc.12.75" target="_blank" >http://dx.doi.org/10.3762/bjoc.12.75</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3762/bjoc.12.75" target="_blank" >10.3762/bjoc.12.75</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and in Vitro Cytotoxicity of Acetylated 3-Fluoro,4-Fluoro and 3,4-Difluoro Analogs of D-glucosamine and D-galactosamine.

Popis výsledku v původním jazyce

This work deals with the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds in selected cancer cells is determined. Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2- azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 3 μM and 54 5 μM, respectively).

Název v anglickém jazyce

Synthesis and in Vitro Cytotoxicity of Acetylated 3-Fluoro,4-Fluoro and 3,4-Difluoro Analogs of D-glucosamine and D-galactosamine.

Popis výsledku anglicky

This work deals with the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds in selected cancer cells is determined. Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2- azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 3 μM and 54 5 μM, respectively).

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CF - Fyzikální chemie a teoretická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Beilstein Journal of Organic Chemistry

ISSN

1860-5397

e-ISSN

—

Svazek periodika

12

Číslo periodika v rámci svazku

Apr 20

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

750-759

Kód UT WoS článku

000374468400001

EID výsledku v databázi Scopus

2-s2.0-84976389300