Cristin-resultat-ID: 1655057
Sist endret: 19. november 2019, 13:52
NVI-rapporteringsår: 2019
Resultat
Vitenskapelig artikkel
2019

Synthesis and antimicrobial activities of N6-hydroxyagelasine analogs and revision of the structure of ageloximes

Bidragsytere:
  • Britt Paulsen
  • Kim Alex Fredriksen
  • Dirk Petersen
  • Louis Maes
  • An Matheeussen
  • Ali-Oddin Naemi
  • mfl.

Tidsskrift

Bioorganic & Medicinal Chemistry
ISSN 0968-0896
e-ISSN 1464-3391
NVI-nivå 1

Om resultatet

Vitenskapelig artikkel
Publiseringsår: 2019
Volum: 27
Hefte: 4
Sider: 620 - 629
Open Access

Importkilder

Scopus-ID: 2-s2.0-85059665320

Beskrivelse Beskrivelse

Tittel

Synthesis and antimicrobial activities of N6-hydroxyagelasine analogs and revision of the structure of ageloximes

Sammendrag

(+)-N6-Hydroxyagelasine D, the enantiomer of the proposed structure of (–)-ageloxime D, as well as N6-hydroxyagelasine analogs were synthesized by selective N-7 alkylation of N6-[tert-butyl(dimethyl)silyloxy]-9-methyl-9H-purin-6-amine in order to install the terpenoid side chain, followed by fluoride mediated removal of the TBDMS-protecting group. N6-Hydroxyagelasine D and the analog carrying a geranylgeranyl side chain displayed profound antimicrobial activities against several pathogenic bacteria and protozoa and inhibited bacterial biofilm formation. However these compounds were also toxic towards mammalian fibroblast cells (MRC-5). The spectral data of N6-hydroxyagelasine D did not match those reported for ageloxime D before. Hence, a revised structure of ageloxime D was proposed. Basic hydrolysis of agelasine D gave (+)-N-[4-amino-6-(methylamino)pyrimidin-5-yl]-N-copalylformamide, a compound with spectral data in full agreement with those reported for (–)-ageloxime D.

Bidragsytere

Britt Paulsen

  • Tilknyttet:
    Forfatter
    ved Kjemisk institutt ved Universitetet i Oslo

Kim Alex Fredriksen

  • Tilknyttet:
    Forfatter
    ved Kjemisk institutt ved Universitetet i Oslo

Dirk Petersen

  • Tilknyttet:
    Forfatter
    ved Kjemisk institutt ved Universitetet i Oslo

Louis Maes

  • Tilknyttet:
    Forfatter
    ved Universiteit Antwerpen

An Matheeussen

  • Tilknyttet:
    Forfatter
    ved Universiteit Antwerpen
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