Copper-free solid-phase synthesis of triazolo[1,5-a][1,4]diazepin-6-ones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F21%3A73608268" target="_blank" >RIV/61989592:15310/21:73608268 - isvavai.cz</a>

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202001403" target="_blank" >https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202001403</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.202001403" target="_blank" >10.1002/adsc.202001403</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Copper-free solid-phase synthesis of triazolo[1,5-a][1,4]diazepin-6-ones

Popis výsledku v původním jazyce

Synthesis of triazolo[1,5-a][1,4]diazepin-6-ones on solid support is reported in this article. Amino acids immobilized on Wang resin were nosylated and alkylated with propargyl alcohol, but-2-yn-1-ol or different 3-phenylprop-2-yn-1-ols using Mitsunobu alkylation conditions. After denosylation, acylation with Fmoc-azidoalanine yielded linear precursors that were thermally cyclized on resin to give immobilized triazolodiazepinones. After cleavage from the polymer support, the target compounds were obtained in high crude purities and good overall yields. Furthermore, the synthetic approach was applied to convenient solid-phase synthesis of oligopeptide containing the triazolodiazepinone moiety as the peptidomimetic heterocyclic constraint.

Název v anglickém jazyce

Copper-free solid-phase synthesis of triazolo[1,5-a][1,4]diazepin-6-ones

Popis výsledku anglicky

Synthesis of triazolo[1,5-a][1,4]diazepin-6-ones on solid support is reported in this article. Amino acids immobilized on Wang resin were nosylated and alkylated with propargyl alcohol, but-2-yn-1-ol or different 3-phenylprop-2-yn-1-ols using Mitsunobu alkylation conditions. After denosylation, acylation with Fmoc-azidoalanine yielded linear precursors that were thermally cyclized on resin to give immobilized triazolodiazepinones. After cleavage from the polymer support, the target compounds were obtained in high crude purities and good overall yields. Furthermore, the synthetic approach was applied to convenient solid-phase synthesis of oligopeptide containing the triazolodiazepinone moiety as the peptidomimetic heterocyclic constraint.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA19-23972S" target="_blank" >GA19-23972S: Multi-FRET fluorescenční sondy aktivované hydrolasami</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

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

Název periodika

Advanced Synthesis &amp; Catalysis

ISSN

1615-4169

e-ISSN

—

Svazek periodika

363

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

1112-1119

Kód UT WoS článku

000603454200001

EID výsledku v databázi Scopus

2-s2.0-85098480796