Evidence map›Paper›PMID 34984767›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022

Synthesis of Polyoxygenated Tropolones and their Antiviral Activity against Hepatitis B Virus and Herpes Simplex Virus-1.

Daniel V Schiavone, Diana M Kapkayeva, Qilan Li, Molly E Woodson, Andreu Gazquez Casals, Lynda A Morrison, John E Tavis, Ryan P Murelli

Abstract read
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

4 citing papers in PubMed.

  1. Review
  2. Article
  3. Article
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4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

8 authors.

Daniel V SchiavoneDepartment of Chemistry, Brooklyn College of the City University of New York, Brooklyn, NY 11210, USA.ORCID http://orcid.org/0000-0001-7736-8645
Diana M KapkayevaDepartment of Chemistry, Brooklyn College of the City University of New York, Brooklyn, NY 11210, USA.
Qilan LiDepartment of Molecular Microbiology and Immunology, Saint Louis University School of Medicine, St. Louis, MO 63104, USA.
Molly E WoodsonDepartment of Molecular Microbiology and Immunology, Saint Louis University School of Medicine, St. Louis, MO 63104, USA.
Andreu Gazquez CasalsDepartment of Molecular Microbiology and Immunology, Saint Louis University School of Medicine, St. Louis, MO 63104, USA.
Lynda A MorrisonDepartment of Molecular Microbiology and Immunology, Saint Louis University School of Medicine, St. Louis, MO 63104, USA.
John E TavisDepartment of Molecular Microbiology and Immunology, Saint Louis University School of Medicine, St. Louis, MO 63104, USA.ORCID http://orcid.org/0000-0002-8711-4240
Ryan P MurelliDepartment of Chemistry, Brooklyn College of the City University of New York, Brooklyn, NY 11210, USA.ORCID http://orcid.org/0000-0002-4247-3936

Funding

Development and Exploitation of New Synthetic Strategies for TropolonesSC1GM111158 · NIGMS · BROOKLYN COLLEGE · PI MURELLI, RYAN · 2015 to 2023
$3.1M
Optimization of alpha-hydroxytropolones as novel inhibitors of the HBV RNaseHR01AI122669 · NIAID · SAINT LOUIS UNIVERSITY · PI TAVIS, JOHN E · 2016 to 2020
$2.2M
HBV RNaseH inhibitors: Effects on HBV biology and resistance developmentR01AI148362 · NIAID · SAINT LOUIS UNIVERSITY · PI TAVIS, JOHN E · 2020 to 2024
$1.9M
National Institute of Allergy and Infectious Diseases RO1AI148362National Institute of Allergy and Infectious Diseases RO1AI22669NIAID NIH HHS R01 AI122669NIAID NIH HHS R01 AI148362NIGMS NIH HHS SC1 GM111158NIGMS NIH HHS SC1GM111158
6 · The paper itself

Abstract

Polyoxygenated tropolones possess a broad range of biological activity, and as a result are promising lead structures or fragments for drug development. However, structure-function studies and subsequent optimization have been challenging, in part due to the limited number of readily available tropolones and the obstacles to their synthesis. Oxidopyrylium [5+2] cycloaddition can effectively generate a diverse array of seven-membered ring carbocycles, and as a result can provide a highly general strategy for tropolone synthesis. Here, we describe the use of 3-hydroxy-4-pyrone-based oxidopyrylium cycloaddition chemistry in the synthesis of functionalized 3,7-dimethoxytropolones, 3,7-dihydroxytropolones, and isomeric 3-hydroxy-7-methoxytropolones through complementary benzyl alcohol-incorporating procedures. The antiviral activity of these molecules against herpes simplex virus-1 and hepatitis B virus is also described, highlighting the value of this approach and providing new structure-function insights relevant to their antiviral activity.

Indexed as

Herpesvirus 1, HumanTropoloneAntiviral AgentsCycloaddition ReactionHepatitis B virusAntiviral AgentsTropolonehepatitis B antiviralsherpes simplex virus antiviralsoxidopyrylium cycloadditionstructure-function analysistropolones

Identifiers

PMID34984767
PMCPMC8858858

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Registered trials

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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.