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Issue 7, 2019
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Importance of lipophilicity for potent anti-herpes simplex virus-1 activity of α-hydroxytropolones

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Abstract

We previously reported that troponoid compounds profoundly inhibit replication of herpes simplex virus (HSV)-1 and HSV-2 in cell culture, including acyclovir-resistant mutants. Synthesis of 26 alpha-hydroxylated tropolones (αHTs) led to a preliminary structure–activity relationship highlighting the potency of bi-phenyl side chains. Here, we explore the structure–activity relationship in more detail, with a focus on various biaryl and other lipophilic molecules. Along with our prior structure–function analysis, we present a refined structure–activity relationship that reveals the importance of the lipophilicity and nature of the side chain for potent anti-HSV-1 activity in cells. We expect this new information will help guide future optimization of αHTs as HSV antivirals.

Graphical abstract: Importance of lipophilicity for potent anti-herpes simplex virus-1 activity of α-hydroxytropolones

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Publication details

The article was received on 16 Apr 2019, accepted on 24 May 2019 and first published on 30 May 2019


Article type: Research Article
DOI: 10.1039/C9MD00225A
Med. Chem. Commun., 2019,10, 1173-1176

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    Importance of lipophilicity for potent anti-herpes simplex virus-1 activity of α-hydroxytropolones

    A. J. Berkowitz, A. D. Franson, A. Gazquez Cassals, K. A. Donald, A. J. Yu, A. K. Garimallaprabhakaran, L. A. Morrison and R. P. Murelli, Med. Chem. Commun., 2019, 10, 1173
    DOI: 10.1039/C9MD00225A

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