ArticleOrganic & biomolecular chemistry2017
Synthesis and biological assessment of 3,7-dihydroxytropolones.
Article in Organic & biomolecular chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 32 citations in OpenAlex.
- Uncovering the Origins of Selectivity in Non-Heme Iron Dioxygenase-Catalyzed Tropolone Biosynthesis.The journal of physical chemistry. B · 2025Article
- In vitro evaluation of tropolone absorption, metabolism, and clearance.Antiviral research · 2023Article
- Lactam-fused tropolones: a new tunable, environmentally sensitive fluorophore class.Organic & biomolecular chemistry · 2023Article
- Carbocycloaddition Strategies for Troponoid Synthesis.Tetrahedron · 2023Article
- Synthesis of Polyoxygenated Tropolones and their Antiviral Activity against Hepatitis B Virus and Herpes Simplex Virus-1.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- RhChemical science · 2022Article
- Effects of Troponoids on Mitochondrial Function and Cytotoxicity.Antimicrobial agents and chemotherapy · 2022Article
- Article
- In search of therapeutic candidates for HIV/AIDS: rational approaches, design strategies, structure-activity relationship and mechanistic insights.RSC advances · 2021Review
- Investigations into a Stoichiometrically Equivalent Intermolecular Oxidopyrylium [5 + 2] Cycloaddition Reaction Leveraging 3-Hydroxy-4-pyrone-Based Oxidopyrylium Dimers.The Journal of organic chemistry · 2021Article
- 3,7-Dihydroxytropolones Inhibit Initiation of Hepatitis B Virus Minus-Strand DNA Synthesis.Molecules (Basel, Switzerland) · 2020Article
- Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade.Chemical communications (Cambridge, England) · 2020Article
- Article
- Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions.The Journal of organic chemistry · 2019Article
- Importance of lipophilicity for potent anti-herpes simplex virus-1 activity of α-hydroxytropolones.MedChemComm · 2019Article
- Spectrophotometric determination of α-hydroxytropolone pTetrahedron letters · 2019Article
- Troponoid Atropisomerism: Studies on the Configurational Stability of Tropone-Amide Chiral Axes.Organic letters · 2019Article
- Divergent synthesis of a thiolate-based α-hydroxytropolone library with a dynamic bioactivity profile.RSC advances · 2019Article
- Sensitivity of the C-Terminal Nuclease Domain of Kaposi's Sarcoma-Associated Herpesvirus ORF29 to Two Classes of Active-Site Ligands.Antimicrobial agents and chemotherapy · 2018Article
- Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018).Tetrahedron · 2018Article
Corrections and comments
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Authors and funding
19 authors at 5 institutions in 3 countries.
Funding
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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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.