Synthesis of furanone-based natural product analogues with quorum sensing antagonist activity

TY - JOUR

T1 - Synthesis of furanone-based natural product analogues with quorum sensing antagonist activity

AU - Hjelmgaard, Thomas

AU - Persson, Tobias

AU - Rasmussen, Thomas B

AU - Givskov, Michael

AU - Nielsen, John

N1 - Keywords: Bacterial Proteins; Biological Factors; Furans

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

M3 - Journal article

C2 - 12837536

SN - 0968-0896

VL - 11

SP - 3261

EP - 3271

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 15

ER -