Gold-Catalyzed Solid-Phase Synthesis of 3,4-Dihydropyrazin-2(1H)-ones: Relevant Pharmacophores and Peptide Backbone Constraints

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F17%3A73584394" target="_blank" >RIV/61989592:15310/17:73584394 - isvavai.cz</a>

Result on the web

<a href="http://pubs.acs.org/doi/ipdf/10.1021/acscombsci.7b00117" target="_blank" >http://pubs.acs.org/doi/ipdf/10.1021/acscombsci.7b00117</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acscombsci.7b00117" target="_blank" >10.1021/acscombsci.7b00117</a>

Result language

angličtina

Original language name

Gold-Catalyzed Solid-Phase Synthesis of 3,4-Dihydropyrazin-2(1H)-ones: Relevant Pharmacophores and Peptide Backbone Constraints

Original language description

Here, we report the efficient solid-phase synthesis of N-propargyl peptides using Fmoc-amino acids and propargyl alcohol as key building blocks. Gold-catalyzed nucleophilic addition to the triple bond induced C-N bond formation, which triggered intramolecular cyclization, yielding 1,3,4-trisubstituted-5-methyl-3,4-dihydropyrazin-2(1H)-ones. Conformations of acyclic and constrained peptides were compared using a two-step conformer distribution analysis at the molecular mechanics level and density functional theory. The results indicated that the incorporation of heterocyclic molecular scaffold into a short peptide sequence adopted extended conformation of peptide chain. The amide bond adjacent to the constraint did not show significant preference for either cis or trans isomerism. Prepared model compounds demonstrate a proof of concept for gold-catalyzed polymer-supported synthesis of variously substituted 3,4-dihydropyrazin-2(1H)-ones for applications in drug discovery and peptide backbone constraints.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/GA16-06446S" target="_blank" >GA16-06446S: From Amino Acids to Nature-Inspired Molecular Scaffolds</a><br>

Continuities

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

Publication year

2017

Confidentiality

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

Name of the periodical

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

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Volume of the periodical

19

Issue of the periodical within the volume

11

Country of publishing house

US - UNITED STATES

Number of pages

6

Pages from-to

681-686

UT code for WoS article

000415392200002

EID of the result in the Scopus database

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