AHL-dependent quorum sensing inhibition: synthesis and biological evaluation of α-(N-alkyl-carboxamide)-γ-butyrolactones and α-(N-alkyl-sulfonamide)-γ-butyrolactones.

Mohamed Boukraa , Mohamad Sabbah (1) , Laurent Soulère (1) , Mohamed L El Efrit , Yves Queneau (2) , Alain Doutheau (1)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 COB - Chimie Organique et Bioorganique

New N-acylhomoserine lactone (AHL) analogues in which the amide function is replaced by a reverse-amide one have been studied as AHL QS modulators. The series of compounds consists of α-(N-alkyl-carboxamide)-γ-butyrolactones, α-(N-alkyl-sulfonamide)-γ-butyrolactones, and 2-(N-alkyl-carboxamide)-cyclopentanones and cyclopentanols. Most active compounds exhibited antagonist activities against LuxR reaching the 30 μM range.

Domaines: Chimie organique

Mohamed Boukraa, Mohamad Sabbah, Laurent Soulère, Mohamed L El Efrit, Yves Queneau, et al.. AHL-dependent quorum sensing inhibition: synthesis and biological evaluation of α-(N-alkyl-carboxamide)-γ-butyrolactones and α-(N-alkyl-sulfonamide)-γ-butyrolactones.. Bioorganic and Medicinal Chemistry Letters, 2011, 21 (22), pp.6876-9. ⟨10.1016/j.bmcl.2011.09.010⟩. ⟨hal-00695861⟩