Evidence map›Paper›PMID 39598657›Full record

ArticleMolecules (Basel, Switzerland)2024

Regioselective Synthesis of Potential Non-Quinonoid Prodrugs of Plasmodione: Antiparasitic Properties Against Two Hemoglobin-Feeding Parasites and Drug Metabolism Studies.

Elena Cesar-Rodo, Baptiste Dupouy, Cécile Häberli, Jean-Marc Strub, David L Williams, Pascal Mäser, Matthias Rottmann, Jennifer Keiser, Don Antoine Lanfranchi, Elisabeth Davioud-Charvet

Abstract read
In one paragraph

Article in Molecules (Basel, Switzerland), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Article
  2. 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.

Elena Cesar-RodoLaboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic & Medicinal Chemistry, UMR7042 CNRS-Université de Strasbourg-Université Haute-Alsace, European School of Chemistry, Polymers and Materials (ECPM), 25, Rue Becquerel, F-67087 Strasbourg, France.
Baptiste DupouyLaboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic & Medicinal Chemistry, UMR7042 CNRS-Université de Strasbourg-Université Haute-Alsace, European School of Chemistry, Polymers and Materials (ECPM), 25, Rue Becquerel, F-67087 Strasbourg, France.
Cécile HäberliSwiss Tropical and Public Health Institute, Kreuzstrasse 2, CH-4123 Allschwil, Switzerland.
Jean-Marc StrubLaboratoire de Spectrométrie de Masse BioOrganique (LSMBO), IPHC UMR 7178 CNRS, Université de Strasbourg, F-67087 Strasbourg, France.ORCID 0000-0001-6224-3428
David L WilliamsDepartment of Microbial Pathogens and Immunity, Rush University Medical Center, 1735 West Harrison Street, Chicago, IL 60612, USA.ORCID 0000-0002-6815-4909
Pascal MäserSwiss Tropical and Public Health Institute, Kreuzstrasse 2, CH-4123 Allschwil, Switzerland.ORCID 0000-0003-3122-1941
Matthias RottmannSwiss Tropical and Public Health Institute, Kreuzstrasse 2, CH-4123 Allschwil, Switzerland.
Jennifer KeiserSwiss Tropical and Public Health Institute, Kreuzstrasse 2, CH-4123 Allschwil, Switzerland.ORCID 0000-0003-0290-3521
Don Antoine LanfranchiLaboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic & Medicinal Chemistry, UMR7042 CNRS-Université de Strasbourg-Université Haute-Alsace, European School of Chemistry, Polymers and Materials (ECPM), 25, Rue Becquerel, F-67087 Strasbourg, France.
Elisabeth Davioud-CharvetLaboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic & Medicinal Chemistry, UMR7042 CNRS-Université de Strasbourg-Université Haute-Alsace, European School of Chemistry, Polymers and Materials (ECPM), 25, Rue Becquerel, F-67087 Strasbourg, France.ORCID 0000-0001-7026-4034

Funding

Agence Nationale de la Recherche (ANR) ANR-22-CE93-0005-01NIH HHS 1R01AI065622-01A2
6 · The paper itself

Abstract

Ψ-1,4-naphthoquinones (Ψ-NQ) are non-quinoid compounds in which aromaticity-found in 1,4-naphthoquinones-is broken by the introduction of an angular methyl at C-4a or -8a. This series was designed to act as prodrugs of 1,4-naphthoquinones in an oxidative environment. Furthermore, from a medicinal chemistry point of view, the loss of planarity of the scaffold might lead to an improved solubility and circumvent the bad reputation of quinones in the pharmaceutical industry. In this work, we illustrated the concept by the synthesis of Ψ -plasmodione regioisomers as prodrugs of the antimalarial plasmodione. The presence of a chiral center introduces a new degree of freedom to be controlled by enantioselectivity and regioselectivity of the cycloaddition in the Diels-Alder reaction. The first strategy that was followed was based on the use of a chiral enantiopure sulfoxide to govern the stereoselective formation of (+)Ψ-NQ or (-)Ψ-NQ, depending on the chirality of the sulfoxide (

Indexed as

AntimalarialsNaphthoquinonesProdrugsAnimalsAntiparasitic AgentsCycloaddition ReactionHemoglobinsMolecular StructurePlasmodium falciparumStereoisomerism1,4-naphthoquinoneAntimalarialsAntiparasitic AgentsHemoglobinsNaphthoquinonesProdrugsangular methylantiplasmodialantischistosomalDiels–Alder cycloadditionhemoglobinplasmodioneprodrug

Identifiers

PMID39598657
PMCPMC11596610

What OpenQuestion holds

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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.