Synthesis and biological assessment of 3,7-dihydroxytropolonesElectronic supplementary information (ESI) available. See DOI: 10.1039/C7OB02453C
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...
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Main Authors | , , , , , , , , , , , , , , , , , , |
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Format | Journal Article |
Published |
19.12.2017
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Online Access | Get full text |
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Summary: | 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.
A new 3,7-dihydroxytropolone synthetic strategy provides access to a proposed natural product precursor and potent antiviral compounds. |
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Bibliography: | 10.1039/C7OB02453C Electronic supplementary information (ESI) available. See DOI |
ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c7ob02453c |