Synthesis and biological assessment of 3,7-dihydroxytropolones
Literature Information
Publication Date
2017-10-24
DOI
10.1039/C7OB02453C
Impact Factor
3.876
Authors
L. A. Morrison, T. Masaoka, J. A. Wilson, E. Lomonosova, H. Zhao, B. S. Patel, S. H. Datla, S. G. Hoft, S. J. Majidi, L. Tang, J. E. Tavis, S. F. J. Le Grice, J. A. Beutler
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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.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
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4,4-Difluoro-2-methyl-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-proline
CAS Number:
1194032-23-9
Molecular Formula:
C11H17F2NO4
![7-Bromo-5-chloro-1H-pyrazolo[4,3-b]pyridine structure](https://static.chemtradehub.com/structs/135/1351813-70-1-a716.webp "7-Bromo-5-chloro-1H-pyrazolo[4,3-b]pyridine structure")
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