Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives

被引：35
|
作者：
Goktas, Fusun [1 ]
Vanderlinden, Evelien [2 ]
Naesens, Lieve [2 ]
Cesur, Nesrin [1 ]
Cesur, Zafer [1 ]
机构：
[1] Istanbul Univ, Fac Pharm, Dept Pharmaceut Chem, TR-34116 Istanbul, Turkey
[2] Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2012年 / 20卷 / 24期
关键词：
Adamantane; Spirothiazolidinone; Microwave; Antiviral; Influenza virus; Hemagglutinin; INFLUENZA-A VIRUS; HEMAGGLUTININ; INHIBITORS; AGENTS;
D O I：
10.1016/j.bmc.2012.09.064
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A microwave-assisted three-component one-pot cyclocondensation method was applied for the synthesis of novel N-(1-thia-4-azaspiro[4.5] decan-4-yl)carboxamide compounds carrying an adamantyl moiety. The structures of the compounds were confirmed by spectral and elemental analysis. All compounds were evaluated for antiviral activity against influenza A (H1N1 and H3N2) and influenza B virus in MDCK cell cultures. The compounds displayed a confined structure-activity relationship. The N-(2,8-dimethyl-3-oxo-1-thia-4-azaspiro[4.5] dec-4-yl)adamantane-1-carboxamide 3b was the most potent inhibitor [antiviral EC50: 1.4 mu M against influenza A/H3N2 virus]. Its strong inhibitory effect in a virus hemolysis assay supports that 3b acts as an influenza virus fusion inhibitor by preventing the conformational change of the influenza virus hemagglutinin at low pH. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7155 / 7159
页数：5
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