McGlacken, GP,McSweeney, CM,O'Brien, T,Lawrence, SE,Elcoate, CJ,Reen, FJ,O'Gara, F;

2010

January

Tetrahedron

Synthesis of 3-halo-analogues of HHQ, subsequent cross-coupling and first crystal structure of Pseudomonas quinolone signal (PQS)

Validated

()

PQS HHQ Quorum signaling Quinolone Pd-catalysis AERUGINOSA DERIVATIVES MOLECULES COMMUNICATION

51

5919

5921

2-Aryl- and 2-alkyl-quinolin-4-ones and their N-substituted derivatives have several important biological functions such as the Pseudomonas quinolone signal (PQS) molecule participation in quorum sensing. Herein, we report the synthesis of its biological precursor, 2-heptyl-4-hydroxy-quinoline (HHQ) and possible isosteres of PQS; the C-3 Cl. Br and I analogues. N-Methylation of the iodide was also feasible and the usefulness of this compound showcased in Pd-catalysed cross-coupling reactions, thus allowing access to a diverse set of biologically important molecules. The first crystal structure of PQS is also included. (C) 2010 Elsevier Ltd. All rights reserved.

DOI 10.1016/j.tetlet.2010.09.013