Evidence map›Paper›PMID 22777178›Full record

ArticleOrganic & biomolecular chemistry2012

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents.

Don Antoine Lanfranchi, Elena Cesar-Rodo, Benoît Bertrand, Hsin-Hung Huang, Latasha Day, Laure Johann, Mourad Elhabiri, Katja Becker, David L Williams, Elisabeth Davioud-Charvet

Abstract read
In one paragraph

Article in Organic & biomolecular chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.

0numbers the graph read from it
0cells of the map it votes in
20citing papers in PubMed
2.6field-weighted citation impact, top 12% of its field
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

20 citing papers in PubMed, 60 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Review
  6. Article
  7. Menadione: a platform and a target to valuable compounds synthesis.Beilstein journal of organic chemistry · 2022
    Review
  8. PfMFR3: A Multidrug-Resistant Modulator inACS infectious diseases · 2021
    Article
  9. Article
  10. Review
  11. Review
  12. Article
  13. Article
  14. Article
  15. Article
  16. QSAR modeling and chemical space analysis of antimalarial compounds.Journal of computer-aided molecular design · 2017
    Article
  17. Article
  18. Article
  19. Cytotoxicity, hemolysis andToxicology reports · 2016
    Article
  20. Article
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

10 authors at 4 institutions in 3 countries.

Don Antoine LanfranchiEuropean School of Chemistry, Polymers and Materials (ECPM) University of Strasbourg, UMR CNRS 7509, 25 Rue Becquerel, F-67087 Strasbourg, France. elisabeth.davioud@unistra.fr.
Elena Cesar-RodoEuropean School of Chemistry, Polymers and Materials (ECPM) University of Strasbourg, UMR CNRS 7509, 25 Rue Becquerel, F-67087 Strasbourg, France. elisabeth.davioud@unistra.fr.
Benoît BertrandEuropean School of Chemistry, Polymers and Materials (ECPM) University of Strasbourg, UMR CNRS 7509, 25 Rue Becquerel, F-67087 Strasbourg, France. elisabeth.davioud@unistra.fr.
Hsin-Hung HuangDepartment of Immunology/Microbiology, Rush University Medical Center, 1735 West Harrison Street, Chicago, IL 60612, USA.
Latasha DayDepartment of Immunology/Microbiology, Rush University Medical Center, 1735 West Harrison Street, Chicago, IL 60612, USA.
Laure JohannEuropean School of Chemistry, Polymers and Materials (ECPM) University of Strasbourg, UMR CNRS 7509, 25 Rue Becquerel, F-67087 Strasbourg, France. elisabeth.davioud@unistra.fr.
Mourad ElhabiriEuropean School of Chemistry, Polymers and Materials (ECPM) University of Strasbourg, UMR CNRS 7509, 25 Rue Becquerel, F-67087 Strasbourg, France. elisabeth.davioud@unistra.fr.
Katja BeckerInterdisciplinary Research Center, Nutritional Biochemistry, Justus Liebig University Giessen, Heinrich-Buff-Ring 26-32, D-35392 Giessen, Germany.
David L WilliamsDepartment of Immunology/Microbiology, Rush University Medical Center, 1735 West Harrison Street, Chicago, IL 60612, USA.
Elisabeth Davioud-CharvetEuropean School of Chemistry, Polymers and Materials (ECPM) University of Strasbourg, UMR CNRS 7509, 25 Rue Becquerel, F-67087 Strasbourg, France. elisabeth.davioud@unistra.fr.
Centre National de la Recherche Scientifique · FRRush University Medical Center · USUniversité de Strasbourg · FRUniversity of Giessen · DE

Funding

Redox Balance & Drug Development in Schistosoma mansoniR01AI065622 · NIAID · RUSH UNIVERSITY MEDICAL CENTER · PI WILLIAMS, DAVID LEE · 2007 to 2011
$1.4M
NIAID NIH HHS HHSN272201000005CNIAID NIH HHS HHSN272201000005INIAID NIH HHS R01 AI065622NIAID NIH HHS R01AI065622
6 · The paper itself

Abstract

Improving the solubility of polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels-Alder reaction. The antimalarial and the antischistosomal activities of these polysubstituted aza-1,4-naphthoquinone derivatives were evaluated and led to the selection of distinct compounds for antimalarial versus antischistosomal action. The Ag(II)-assisted oxidative radical decarboxylation of the phenyl acetic acids using AgNO(3) and ammonium peroxodisulfate was modified to generate the 3-picolinyl-menadione with improved pharmacokinetic parameters, high antimalarial effects and capacity to inhibit the formation of β-hematin.

Indexed as

AnimalsAntimalarialsHeminHumansMalaria, FalciparumMethemoglobinMiceNaphthoquinonesPlasmodium falciparumQuinolinesSchistosoma mansoniSchistosomiasis mansoniSchistosomicidesSolubility1,4-naphthoquinoneAntimalarialsHeminMethemoglobinNaphthoquinonesQuinolinesSchistosomicides

Identifiers

PMID22777178
PMCPMC3423093
OpenAlexW2043530832

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

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.