Novel thienopyrimidones targeting hepatic and erythrocytic stages of Plasmodium parasites with increased microsomal stability.


Journal

European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510

Informations de publication

Date de publication:
05 Dec 2023
Historique:
received: 03 07 2023
revised: 02 10 2023
accepted: 11 10 2023
medline: 3 11 2023
pubmed: 20 10 2023
entrez: 19 10 2023
Statut: ppublish

Résumé

Based on the structure of a previously identified hit, Gamhepathiopine 1, which showed promising antiplasmodial activity, but poor microsomal stability, several strategies were investigated to improve the metabolic stability of the compounds. This included the introduction of fluorine or deuterium atoms, as well as carbocyclic groups. Among the new compounds, the 2-aminocyclobutyl derivative 5g demonstrated enhanced microsomal stability compared to compound 1, while retaining antiplasmodial activity against erythrocytic and hepatic stages of Plasmodium, without significant cytotoxicity against primary hepatocytes.

Identifiants

pubmed: 37857143
pii: S0223-5234(23)00840-1
doi: 10.1016/j.ejmech.2023.115873
pii:
doi:

Substances chimiques

Antimalarials 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

115873

Informations de copyright

Copyright © 2023 Elsevier Masson SAS. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Prisca Lagardère (P)

Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Université de Montpellier, ENSCM, UFR des Sciences Pharmaceutiques et Biologiques, Montpellier, France.

Romain Mustière (R)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 13385 Marseille cedex 05, France.

Nadia Amanzougaghene (N)

Centre d'Immunologie et des Maladies Infectieuses (CIMI), INSERM, CNRS, Sorbonne Université, Paris, France.

Sébastien Hutter (S)

Aix Marseille Université, IRD, AP-HM, SSA, VITROME, Marseille, France.

Marion Casanova (M)

Aix Marseille Université, IRD, AP-HM, SSA, VITROME, Marseille, France.

Jean-François Franetich (JF)

Centre d'Immunologie et des Maladies Infectieuses (CIMI), INSERM, CNRS, Sorbonne Université, Paris, France.

Shahin Tajeri (S)

Centre d'Immunologie et des Maladies Infectieuses (CIMI), INSERM, CNRS, Sorbonne Université, Paris, France.

Aurélie Malzert-Fréon (A)

CERMN, Université de Caen Normandie, UNICAEN, France.

Sophie Corvaisier (S)

CERMN, Université de Caen Normandie, UNICAEN, France.

Marc Since (M)

CERMN, Université de Caen Normandie, UNICAEN, France.

Nadine Azas (N)

Aix Marseille Université, IRD, AP-HM, SSA, VITROME, Marseille, France.

Patrice Vanelle (P)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 13385 Marseille cedex 05, France; AP-HM, Hôpital Conception, Service Central de la Qualité et de l'Information Pharmaceutiques, 13005, Marseille, France.

Pierre Verhaeghe (P)

Univ. Grenoble Alpes, CNRS, DPM UMR 5063, F-38041, Grenoble, France; LCC-CNRS Université de Toulouse, CNRS, UPS, Toulouse, France; CHU de Nîmes, Service de Pharmacie, Nîmes, France.

Nicolas Primas (N)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 13385 Marseille cedex 05, France; AP-HM, Hôpital Conception, Service Central de la Qualité et de l'Information Pharmaceutiques, 13005, Marseille, France.

Dominique Mazier (D)

Centre d'Immunologie et des Maladies Infectieuses (CIMI), INSERM, CNRS, Sorbonne Université, Paris, France.

Nicolas Masurier (N)

Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Université de Montpellier, ENSCM, UFR des Sciences Pharmaceutiques et Biologiques, Montpellier, France. Electronic address: nicolas.masurier@umontpellier.fr.

Vincent Lisowski (V)

Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Université de Montpellier, ENSCM, UFR des Sciences Pharmaceutiques et Biologiques, Montpellier, France. Electronic address: vincent.lisowski@umontpellier.fr.

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Classifications MeSH