Synthesis and antiherpetic activity of N-(3-amino-1-adamantyl)calix[4] arenes

被引：0

作者：

Motornaya A.E. ^{[1
]}

Alimbarova L.M. ^{[1
]}

Shokova É.A. ^{[2
]}

Kovalev V.V. ^{[1
]}

机构：

[1] Department of Chemistry, Moscow State University, Moscow

[2] Ivanovsky Institute of Virology, Russian Academy of Medical Sciences, Moscow

来源：

Pharmaceutical Chemistry Journal | 2006年 / 40卷 / 2期

基金：

俄罗斯基础研究基金会;

关键词：

Amantadine; Compound IIIa; Rimantadine; Infectious Titer; Antiherpetic Activity;

D O I：

10.1007/s11094-006-0060-4

中图分类号：

学科分类号：

摘要：

p-(3-Amino-1-adamantyl)calix[4]arenes with free and alkylated lower rim, representing conjugates of the aminoadamantane pharmacophore fragment and the calixarene platform, were synthesized for the first time by the Curtius rearrangement route starting from p-(3-carboxy-1-adamantyl)calix[4]arenes. The synthesized compounds were evaluated for activity against herpes simplex virus 2 (HSV-2). The nonalkylated compound with free phenol hydroxy groups is the first aminoadamantylcalixarene reported to possess antiviral properties (chemotherapeutic safety index, SI ≈ 12.5). Alkylation at the lower rim of the calixarene platform leads to an increase in cytotoxicity and to the disappearance of anti-HSV activity. © 2006 Springer Science+Business Media, Inc.

引用

页码：68 / 72

页数：4

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