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Synthesis and biological assessment of 3,7-dihydroxytropolones

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Abstract

3,7-Dihydroxytropolones (3,7-dHTs) are highly oxygenated troponoids that have been identified as lead compounds for several human diseases. To date, structure–function studies on these molecules have been limited due to a scarcity of synthetic methods for their preparation. New synthetic strategies towards structurally novel 3,7-dHTs would be valuable in further studying their therapeutic potential. Here we describe the successful adaptation of a [5 + 2] oxidopyrilium cycloaddition/ring-opening for 3,7-dHT synthesis, which we apply in the synthesis of a plausible biosynthetic intermediate to the natural products puberulic and puberulonic acid. We have also tested these new compounds in several biological assays related to human immunodeficiency virus (HIV), hepatitis B virus (HBV) and herpes simplex virus (HSV) in order to gain insight into structure-functional analysis related to antiviral troponoid development.

Graphical abstract: Synthesis and biological assessment of 3,7-dihydroxytropolones

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Publication details

The article was received on 03 Oct 2017, accepted on 24 Oct 2017 and first published on 24 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02453C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis and biological assessment of 3,7-dihydroxytropolones

    D. R. Hirsch, D. V. Schiavone, A. J. Berkowitz, L. A. Morrison, T. Masaoka, J. A. Wilson, E. Lomonosova, H. Zhao, B. S. Patel, S. H. Datla, S. G. Hoft, S. J. Majidi, R. K. Pal, E. Gallicchio, L. Tang, J. E. Tavis, S. F. J. Le Grice, J. A. Beutler and R. P. Murelli, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02453C

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