Journal
JOURNAL OF MEDICINAL CHEMISTRY
Volume 52, Issue 19, Pages 6053-6061Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jm900950d
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Funding
- Hungarian Research Fund OTKA [79126, T-46186, OTKA-NKTH CK 77515, NK 68578]
- Flemish Fonds voor Wetenschappelijk Onderzoek (FWO) [9.0188.07]
- International Consortium for Anti-Virals (ICAV)
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Semisynthetic, lipophilic ristocetin and teicoplanin derivatives were prepared starting from ristocetin aglycon and teicoplanin psi-aglycon (N-acetyl-D-glucosaminyl aglycoteicoplanin). The terminal amino functions of the aglycons were converted into azido form by triflic azide. Copper catalyzed 1,3-dipolar cycloaddition reaction with lipophilic alkynes resulted in the title compounds. Two of the teicoplanin derivatives showed very good MIC and MBC values against various Gram-positive bacteria, including vanA enterococci. The aggregation and interaction of a n-decyl derivative with bacterial cell wall components Was Studied. One of the lipophilic ristocetin derivatives displayed favorable anti-influenza virus activity.
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