Title: Diazo transfer-click reaction route to new, lipophilic teicoplanin and ristocetin aglycon derivatives with high antibacterial and anti-influenza virus activity: an aggregation and receptor binding study
Authors: Pintér, Gábor ×
Batta, Gyula
Kéki, Sándor
Mándi, Attila
Komáromi, István
Takács-Novák, Krisztina
Sztaricskai, Ferenc
Röth, Erzsébet
Ostorházi, Eszter
Rozgonyi, Ferenc
Naesens, Lieve
Herczegh, Pál #
Issue Date: Oct-2009
Publisher: ACS Publications
Series Title: Journal of Medicinal Chemistry vol:52 issue:19 pages:6053-6061
Abstract: 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.
ISSN: 0022-2623
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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