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
Department of Pharmaceutical Chemistry, University of Debrecen, Debrecen, Hungary.
J Med Chem. 2009 Oct 8;52(19):6053-61. doi: 10.1021/jm900950d.
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.
半合成的亲脂性瑞斯托菌素和替考拉宁衍生物是从瑞斯托菌素苷元以及替考拉宁ψ-苷元（N-乙酰-D-葡糖胺基替考拉宁）开始制备的。苷元的末端氨基功能通过三氟甲磺酸叠氮化物转化为叠氮形式。与亲脂性炔烃的铜催化1,3-偶极环加成反应产生了标题化合物。两种替考拉宁衍生物对包括vanA肠球菌在内的各种革兰氏阳性菌显示出非常好的最低抑菌浓度（MIC）和最低杀菌浓度（MBC）值。研究了一种正癸基衍生物与细菌细胞壁成分的聚集和相互作用。一种亲脂性瑞斯托菌素衍生物表现出良好的抗流感病毒活性。
