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 Bindi
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- 作者：Gbor Pintr ; Gyula Batta ; Sndor Kki ; Attila Mndi ; Istvn Komromi ; Krisztina Takcs-Novk ; Ferenc Sztaricskai ; Erzsbet Rth ; Eszter Ostorhzi ; Ferenc Rozgonyi ; Lieve Naesens ; Pl Herczegh
- 刊名：Journal of Medicinal Chemistry
- 出版年：2009
- 出版时间：October 8, 2009
- 年：2009
- 卷：52
- 期：19
- 页码：6053-6061
- 全文大小：875K
- 年卷期：v.52,no.19(October 8, 2009)
- ISSN：1520-4804
文摘
Semisynthetic, lipophilic ristocetin and teicoplanin derivatives were prepared starting from ristocetin aglycon and teicoplanin ψ-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.