8-Alkynyl-3-nitroimidazopyridines display potent antitrypanosomal activity against both T. b. brucei and cruzi.

Dose-Response Relationship, Drug Molecular Structure Nitroimidazoles / chemical synthesis Parasitic Sensitivity Tests Pyridines / chemical synthesis Structure-Activity Relationship Trypanocidal Agents / chemical synthesis Trypanosoma brucei brucei / drug effects Trypanosoma cruzi / drug effects
Comet assay Imidazo[1,2-a]pyridine Kinetoplastids Nitroaromatic Nitroreductases SARs

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:
15 Sep 2020
Historique:
received: 17 03 2020
revised: 09 06 2020
accepted: 09 06 2020
pubmed: 12 7 2020
medline: 2 4 2021
entrez: 12 7 2020
Statut: ppublish

Résumé

An antikinetoplastid pharmacomodulation study was done at position 8 of a previously identified pharmacophore in 3-nitroimidazo[1,2-a]pyridine series. Twenty original derivatives bearing an alkynyl moiety were synthesized via a Sonogashira cross-coupling reaction and tested in vitro, highlighting 3 potent (40 nM ≤ EC

Identifiants

DOI: 10.1016/j.ejmech.2020.112558 PMID: 32652409
pubmed: 32652409
pii: S0223-5234(20)30530-4
doi: 10.1016/j.ejmech.2020.112558
pii:
doi:

Substances chimiques

Nitroimidazoles 0
Pyridines 0
Trypanocidal Agents 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

112558

Informations de copyright

Copyright © 2020 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

Cyril Fersing (C)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS30064, 13385, Marseille Cedex 05, France.

Clotilde Boudot (C)

Université de Limoges, UMR Inserm 1094, Neuroépidémiologie Tropicale, Faculté de Pharmacie, 2 rue du Dr Marcland, 87025, Limoges, France.

Caroline Castera-Ducros (C)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS30064, 13385, Marseille Cedex 05, France.

Emilie Pinault (E)

Université de Limoges, BISCEm Mass Spectrometry Platform, CBRS, 2 rue du Pr. Descottes, F-87025, Limoges, France.

Sébastien Hutter (S)

Aix Marseille Univ, IHU Méditerranée Infection, UMR VITROME, Tropical Eukaryotic Pathogens, 19-21 Boulevard Jean Moulin, 13005, Marseille, France.

Romain Paoli-Lombardo (R)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS30064, 13385, Marseille Cedex 05, France.

Nicolas Primas (N)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS30064, 13385, Marseille Cedex 05, France.

Julien Pedron (J)

LCC-CNRS Université de Toulouse, CNRS, UPS, Toulouse, France.

Line Seguy (L)

LCC-CNRS Université de Toulouse, CNRS, UPS, Toulouse, France.

Sandra Bourgeade-Delmas (S)

UMR 152 PHARMA-DEV, Université de Toulouse, IRD, UPS, Toulouse, France.

Alix Sournia-Saquet (A)

LCC-CNRS Université de Toulouse, CNRS, UPS, Toulouse, France.

Jean-Luc Stigliani (JL)

LCC-CNRS Université de Toulouse, CNRS, UPS, Toulouse, France.

Jean-Yves Brossas (JY)

AP-HP, Groupe Hospitalier Pitié-Salpêtrière, Service de Parasitologie Mycologie, Paris, France.

Luc Paris (L)

AP-HP, Groupe Hospitalier Pitié-Salpêtrière, Service de Parasitologie Mycologie, Paris, France.

Alexis Valentin (A)

UMR 152 PHARMA-DEV, Université de Toulouse, IRD, UPS, Toulouse, France.

Susan Wyllie (S)

University of Dundee, School of Life Sciences, Division of Biological Chemistry and Drug Discovery, Dow Street, Dundee, DD1 5EH, Scotland, United Kingdom.

Alan H Fairlamb (AH)

University of Dundee, School of Life Sciences, Division of Biological Chemistry and Drug Discovery, Dow Street, Dundee, DD1 5EH, Scotland, United Kingdom.

Élisa Boutet-Robinet (É)

Toxalim (Research Centre in Food Toxicology), Université de Toulouse, INRA, ENVT, INP-Purpan, UPS, Toulouse, France.

Sophie Corvaisier (S)

Normandie Univ, UNICAEN, CERMN, 14000, Caen, France.

Marc Since (M)

Normandie Univ, UNICAEN, CERMN, 14000, Caen, France.

Aurélie Malzert-Fréon (A)

Normandie Univ, UNICAEN, CERMN, 14000, Caen, France.

Alexandre Destere (A)

Department of Pharmacology, Toxicology and Pharmacovigilance, CHU Limoges, INSERM, UMR 1248, University of Limoges, Limoges, France.

Dominique Mazier (D)

CIMI-Paris, Sorbonne Université 91 boulevard de l'Hôpital, 75013, Paris, France.

Pascal Rathelot (P)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS30064, 13385, Marseille Cedex 05, France.

Bertrand Courtioux (B)

Université de Limoges, UMR Inserm 1094, Neuroépidémiologie Tropicale, Faculté de Pharmacie, 2 rue du Dr Marcland, 87025, Limoges, France.

Nadine Azas (N)

Aix Marseille Univ, IHU Méditerranée Infection, UMR VITROME, Tropical Eukaryotic Pathogens, 19-21 Boulevard Jean Moulin, 13005, Marseille, France.

Pierre Verhaeghe (P)

LCC-CNRS Université de Toulouse, CNRS, UPS, Toulouse, France. Electronic address: pierre.verhaeghe@lcc-toulouse.fr.

Patrice Vanelle (P)

Aix Marseille Univ, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS30064, 13385, Marseille Cedex 05, France.

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Classifications MeSH

questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Imidazoles › Nitroimidazoles › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Techniques d'investigation › Évaluation préclinique de médicament › Tests de sensibilité parasitaire › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Pyridines › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Anti-infectieux › Antiparasitaires › Antiprotozoaires › Trypanocides › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Eucaryotes › Euglénozoaires › Kinetoplastida › Trypanosomatina › Trypanosoma › Trypanosoma brucei brucei › 8-Alkynyl-3-nitroimidazopyridines display...
questionsmedicales.fr › Eucaryotes › Euglénozoaires › Kinetoplastida › Trypanosomatina › Trypanosoma › Trypanosoma cruzi › 8-Alkynyl-3-nitroimidazopyridines display...