Synthesis of Novel N-9-Substituted Purine Derivatives from Polymer Supported alpha-Amino Acids

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F15%3A73576783" target="_blank" >RIV/61989592:15110/15:73576783 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61389030:_____/15:00447320 RIV/61989592:15310/15:73576783

Výsledek na webu

<a href="https://pubs.acs.org/doi/10.1021/acscombsci.5b00071" target="_blank" >https://pubs.acs.org/doi/10.1021/acscombsci.5b00071</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acscombsci.5b00071" target="_blank" >10.1021/acscombsci.5b00071</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of Novel N-9-Substituted Purine Derivatives from Polymer Supported alpha-Amino Acids

Popis výsledku v původním jazyce

Solid-phase synthesis of purine derivatives bearing an alpha-amino acid motif in position 9 is described herein. Polymer supported amines were acylated with various Fmoc-alpha-amino acids and, after cleavage of the protecting group, arylation with 4,6-dichloro-5-nitropyrimidine or 2,4-dichloro-5-nitropyrimidine was performed. The second chlorine atom was replaced with various amines. Subsequent reduction of the nitro group, followed by reaction with aldehydes, afforded the purine scaffold. After cleavage from the polymer support, the target compounds were obtained in very good crude purity, good overall yields, and excellent enantiomeric purity. The anticancer activity of prepared compounds was tested in vitro against human cancer cell lines MCF7 and K562, and they were found to have mild, but clear dose-dependent effects.

Název v anglickém jazyce

Synthesis of Novel N-9-Substituted Purine Derivatives from Polymer Supported alpha-Amino Acids

Popis výsledku anglicky

Solid-phase synthesis of purine derivatives bearing an alpha-amino acid motif in position 9 is described herein. Polymer supported amines were acylated with various Fmoc-alpha-amino acids and, after cleavage of the protecting group, arylation with 4,6-dichloro-5-nitropyrimidine or 2,4-dichloro-5-nitropyrimidine was performed. The second chlorine atom was replaced with various amines. Subsequent reduction of the nitro group, followed by reaction with aldehydes, afforded the purine scaffold. After cleavage from the polymer support, the target compounds were obtained in very good crude purity, good overall yields, and excellent enantiomeric purity. The anticancer activity of prepared compounds was tested in vitro against human cancer cell lines MCF7 and K562, and they were found to have mild, but clear dose-dependent effects.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

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

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

—

Svazek periodika

17

Číslo periodika v rámci svazku

7

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

426-432

Kód UT WoS článku

000358026300007

EID výsledku v databázi Scopus

2-s2.0-84953884030