title: Synthesis of furanone-based natural product analogues with quorum sensing antagonist activity.
abstract: The synthesis of 5- and 3-(1'-hydroxyalkyl)-substituted 5H-furan-2-ones 4a-d and 8a-d as well as 5-alkylidene-5H-furan-2-ones 5a-d is described. A study of the structure-activity relationship of these furanone-based natural product analogues towards two different quorum sensing systems is reported. Although the synthesized compounds are not as potent quorum sensing inhibitors as some natural counterparts and a synthetic analogue hereof, interesting structure-activity relationships are seen.
authors.affiliation: Department of Chemistry, Organic Chemistry, Bld. 201, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Thomas
authors.initials: T
authors.lastname: Hjelmgaard
authors.forename: Tobias
authors.initials: T
authors.lastname: Persson
authors.forename: Thomas B
authors.initials: TB
authors.lastname: Rasmussen
authors.forename: Michael
authors.initials: M
authors.lastname: Givskov
authors.forename: John
authors.initials: J
authors.lastname: Nielsen
mesh_terms: D001426:Bacterial Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D001685:Biological Factors / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000378:metabolism; D005663:Furans / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000378:metabolism
chemical_list: D001426:Bacterial Proteins; D001685:Biological Factors; D005663:Furans