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.
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.
Pintér
Gábor
G
Department of Pharmaceutical Chemistry, University of Debrecen, Debrecen, Hungary.
Batta
Gyula
G
Kéki
Sándor
S
Mándi
Attila
A
Komáromi
István
I
Takács-Novák
Krisztina
K
Sztaricskai
Ferenc
F
Röth
Erzsébet
E
Ostorházi
Eszter
E
Rozgonyi
Ferenc
F
Naesens
Lieve
L
Herczegh
Pál
P
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D003979:Diazonium Compounds / Q000737:chemistry* / Q000494:pharmacology; D004317:Doxorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009975:Orthomyxoviridae / Q000187:drug effects; D017334:Teicoplanin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D003979:Diazonium Compounds; C488135:ristocetin aglycon; D017334:Teicoplanin; D004317:Doxorubicin; C063101:teicoplanin aglycone