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Article Dans Une Revue ChemMedChem Année : 2019

2,4‐Disubstituted 5‐Nitroimidazoles Potent against Clostridium difficile

Cédric Spitz
  • Fonction : Auteur
Fanny Mathias
  • Fonction : Auteur
Jean Innocent
  • Fonction : Auteur
Sylvain Pellissier
  • Fonction : Auteur
Carole Di Giorgio
  • Fonction : Auteur
Maxime Crozet
  • Fonction : Auteur
Claire Janoir
Patrice Vanelle

Résumé

Abstract Metronidazole is one of the first‐line treatments for non‐severe Clostridium difficile infections (CDI). However, resistance limits its use in cases of severe and complicated CDI. Structure–activity relationships previously described for the 5‐nitroimidazole series have shown that functionalization at the 2‐ and 4‐positions can impart better activity against parasites and anaerobic bacteria than metronidazole. Herein we report the synthesis of new 2,4‐disubstituted 5‐nitroimidazole compounds that show potent antibacterial activity against C. difficile . We used a vicarious nucleophilic substitution of hydrogen (VNS) reaction to introduce a phenylmethylsulfone at the 4‐position and a unimolecular radical nucleophilic substitution (S RN 1) reaction to introduce an ethylenic function at the 2‐position of the 5‐nitroimidazole scaffold.

Dates et versions

hal-04341841 , version 1 (13-12-2023)

Identifiants

Citer

Cédric Spitz, Fanny Mathias, Séverine Péchiné, Tri Hanh Dung Doan, Jean Innocent, et al.. 2,4‐Disubstituted 5‐Nitroimidazoles Potent against Clostridium difficile. ChemMedChem, 2019, 14 (5), pp.561-569. ⟨10.1002/cmdc.201800784⟩. ⟨hal-04341841⟩

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