2008
DOI: 10.1016/j.bmcl.2008.06.090
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N-Acyl-3-amino-5H-furanone derivatives as new inhibitors of LuxR-dependent quorum sensing: Synthesis, biological evaluation and binding mode study

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Cited by 44 publications
(36 citation statements)
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“…161 In total, six compounds 87-92 were synthesized, three of which incorporated halogen atoms at the 4-position and are thus structurally reminiscent of the D. pulchra furanones (Figure 20).…”
Section: Furanones and Related Structural Analoguesmentioning
confidence: 99%
See 1 more Smart Citation
“…161 In total, six compounds 87-92 were synthesized, three of which incorporated halogen atoms at the 4-position and are thus structurally reminiscent of the D. pulchra furanones (Figure 20).…”
Section: Furanones and Related Structural Analoguesmentioning
confidence: 99%
“…Nonmacrolide antibiotics have also been reported to have effects upon quorum sensing systems in Gramnegative bacteria. Skindersoe et al discovered that the antibiotics iprofloxacin (161) and ceftazidime (162) are capable of decreasing the expression of a range of quorum sensing-regulated virulence factors in P. aeruginosa at subinhibitory concentrations ( Figure 34). 57 In silico docking experiments suggested that these compounds have a low affinity for the LasR receptor site and led the authors to postulate that they may exert their quorum sensing regulatory effects through novel, as yet undetermined, mechanisms.…”
Section: Recognized Drugsmentioning
confidence: 99%
“…[13][14][15] A number of QS-modulating ligands have been designed and synthesized by mimicking the natural auto-inducers such as OdDHL, BHL or PQS. [16][17][18][19][20][21][22][23][24][25][26][27] According to structure-activity relationship (SAR) studies of the synthesized QS ligands, the hydrophilic group (e.g., lactone, quinolone) and the lipophilic alkyl chains are essential for the QS-modulating activity. [28][29][30][31][32][33] Inhibitors that block the complex formation between auto-inducers and the cognate receptors could downregulate the transcription of QS-associated genes and diminish or halt the virulence of P. aeruginosa.…”
mentioning
confidence: 99%
“…2A). According to the modelling, the fluorenyl moiety occupies the space where the lactone moiety of the natural ligand 3-oxo-C 6 -AHL usually binds, 24,38 and is involved in attractive interactions with Trp66 and Trp94 (Fig. 2B).…”
Section: Molecular Modellingmentioning
confidence: 99%
“…[10][11][12][13][14][15][16][17][18][19] In Gram negative bacteria, the autoinducers are mainly N-acyl homoserine lactones (AHLs) and the transcriptional factors are LuxR-type proteins. 19 As part of our research aimed at the discovery of potential modulators of AHLs-dependent transcriptional regulators, [20][21][22][23][24][25] we recently described the computer aided identification of several inhibitors of LuxR dependent quorum sensing, all structurally unrelated to AHL. 26 Such AHL unrelated analogues are still less investigated than more classical AHL analogues.…”
Section: Introductionmentioning
confidence: 99%