Evidence map›Paper›PMID 31842358›Full record

ArticleInternational journal of molecular sciences2019

Less Cytotoxic Protoflavones as Antiviral Agents: Protoapigenone 1'-

Máté Vágvölgyi, Gábor Girst, Norbert Kúsz, Sándor B Ötvös, Ferenc Fülöp, Judit Hohmann, Jean-Yves Servais, Carole Seguin-Devaux, Fang-Rong Chang, Michael S Chen and 2 more

Abstract read
In one paragraph

Article in International journal of molecular sciences, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Review
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  6. Review
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

12 authors.

Máté VágvölgyiInstitute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.
Gábor GirstInstitute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.
Norbert KúszInstitute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.
Sándor B ÖtvösInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Hungary.ORCID 0000-0001-6673-1744
Ferenc FülöpInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Hungary.ORCID 0000-0003-1066-5287
Judit HohmannInstitute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.ORCID 0000-0002-2887-6392
Jean-Yves ServaisDepartment of Infection and Immunity, Luxembourg Institute of Health, L-4354 Esch-sur-Alzette, Luxemburg.
Carole Seguin-DevauxDepartment of Infection and Immunity, Luxembourg Institute of Health, L-4354 Esch-sur-Alzette, Luxemburg.ORCID 0000-0003-0636-5222
Fang-Rong ChangGraduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan.ORCID 0000-0003-2549-4193
Michael S ChenDepartment of Biochemical Science and Technology, College of Life Science, National Taiwan University, Taipei City 10617, Taiwan.
Li-Kwan ChangDepartment of Biochemical Science and Technology, College of Life Science, National Taiwan University, Taipei City 10617, Taiwan.
Attila HunyadiInstitute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.ORCID 0000-0003-0074-3472

Funding

Nemzeti Kutatási Fejlesztési és Innovációs Hivatal K119770Nemzeti Kutatási Fejlesztési és Innovációs Hivatal NN118176
6 · The paper itself

Abstract

Protoflavones, a rare group of natural flavonoids with a non-aromatic B-ring, are best known for their antitumor properties. The protoflavone B-ring is a versatile moiety that might be explored for various pharmacological purposes, but the common cytotoxicity of these compounds is a limitation to such efforts. Protoapigenone was previously found to be active against the lytic cycle of Epstein-Barr virus (EBV). Further, the 5-hydroxyflavone moiety is a known pharmacophore against HIV-integrase. The aim of this work was to prepare a series of less cytotoxic protoflavone analogs and study their antiviral activity against HIV and EBV. Twenty-seven compounds, including 18 new derivatives, were prepared from apigenin through oxidative de-aromatization and subsequent continuous-flow hydrogenation, deuteration, and/or 4'-oxime formation. One compound was active against HIV at the micromolar range, and three compounds showed significant activity against the EBV lytic cycle at the medium-low nanomolar range. Among these derivatives, protoapigenone 1'-

Indexed as

Antineoplastic AgentsCyclohexanonesEthersFlavonesHerpesvirus 4, HumanHumansMagnetic Resonance SpectroscopyMolecular StructureStructure-Activity RelationshipVirus Physiological PhenomenaVirus ReplicationAntineoplastic AgentsCyclohexanonesdiisopropyl etherEthersFlavonesprotoapigenoneantitumorantiviralcontinuous-flow chemistrydrug discoveryEpstein–Barr viruslytic cyclenatural productoximeprotoflavonoid

Identifiers

PMID31842358
PMCPMC6940897

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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.