Synthesis of furanone-based natural product analogues with quorum sensing antagonist activity.
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.
Hjelmgaard
Thomas
T
Department of Chemistry, Organic Chemistry, Bld. 201, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
Persson
Tobias
T
Rasmussen
Thomas B
TB
Givskov
Michael
M
Nielsen
John
J
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
D001426:Bacterial Proteins; D001685:Biological Factors; D005663:Furans