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

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TY  - JOUR
  - McGlacken, Gerard P; McSweeney, Christina M; O'Brien, Timothy; Lawrence, Simon E; Elcoate, Curtis J; Reen, Jerry F; O'Gara, Fergal
  - 2010
  - Unknown
  - Tetrahedron Letters
  - Synthesis of 3-halo-analogues of HHQ, subsequent cross-coupling and first crystal structure of Pseudomonas quinolone signal (PQS).
  - Published
  - ()
  - 51
  - 45
  - 5919
  - 5921
  - 2-Aryl- and 2-alkyl-quinolin-4-ones and their N-substituted derivs. have several important biol. functions such as the Pseudomonas quinolone signal (PQS) mol. participation in quorum sensing. Herein, we report the synthesis of its biol. precursor, 2-heptyl-4-hydroxy-quinoline (HHQ) and possible isosteres of PQS; the C-3 Cl, Br and I analogs. N-Methylation of the iodide was also feasible and the usefulness of this compd. showcased in Pd-catalyzed cross-coupling reactions, thus allowing access to a diverse set of biol. important mols. The first crystal structure of PQS is also included.
  - 0040-4039
DA  - 2010/NaN
ER  - 
@article{V57685683,
   = {McGlacken, Gerard P and  McSweeney, Christina M and  O'Brien, Timothy and  Lawrence, Simon E and  Elcoate, Curtis J and  Reen, Jerry F and  O'Gara, Fergal},
   = {2010},
   = {Unknown},
   = {Tetrahedron Letters},
   = {Synthesis of 3-halo-analogues of HHQ, subsequent cross-coupling and first crystal structure of Pseudomonas quinolone signal (PQS).},
   = {Published},
   = {()},
   = {51},
   = {45},
  pages = {5919--5921},
   = {{2-Aryl- and 2-alkyl-quinolin-4-ones and their N-substituted derivs. have several important biol. functions such as the Pseudomonas quinolone signal (PQS) mol. participation in quorum sensing. Herein, we report the synthesis of its biol. precursor, 2-heptyl-4-hydroxy-quinoline (HHQ) and possible isosteres of PQS; the C-3 Cl, Br and I analogs. N-Methylation of the iodide was also feasible and the usefulness of this compd. showcased in Pd-catalyzed cross-coupling reactions, thus allowing access to a diverse set of biol. important mols. The first crystal structure of PQS is also included.}},
  issn = {0040-4039},
  source = {IRIS}
}
AUTHORSMcGlacken, Gerard P; McSweeney, Christina M; O'Brien, Timothy; Lawrence, Simon E; Elcoate, Curtis J; Reen, Jerry F; O'Gara, Fergal
YEAR2010
MONTHUnknown
JOURNAL_CODETetrahedron Letters
TITLESynthesis of 3-halo-analogues of HHQ, subsequent cross-coupling and first crystal structure of Pseudomonas quinolone signal (PQS).
STATUSPublished
TIMES_CITED()
SEARCH_KEYWORD
VOLUME51
ISSUE45
START_PAGE5919
END_PAGE5921
ABSTRACT2-Aryl- and 2-alkyl-quinolin-4-ones and their N-substituted derivs. have several important biol. functions such as the Pseudomonas quinolone signal (PQS) mol. participation in quorum sensing. Herein, we report the synthesis of its biol. precursor, 2-heptyl-4-hydroxy-quinoline (HHQ) and possible isosteres of PQS; the C-3 Cl, Br and I analogs. N-Methylation of the iodide was also feasible and the usefulness of this compd. showcased in Pd-catalyzed cross-coupling reactions, thus allowing access to a diverse set of biol. important mols. The first crystal structure of PQS is also included.
PUBLISHER_LOCATION
ISBN_ISSN0040-4039
EDITION
URL
DOI_LINK
FUNDING_BODY
GRANT_DETAILS