Microwave and flow syntheses of Pseudomonas quinolone signal (PQS) and analogues

Organic and Biomolecular Chemistry

Volumn 9, Issue 1, 2011, Pages 57-61

  Hodgkinson, James T ^a   Galloway, Warren R J D ^a   Saraf, Shreya ^a   Baxendale, Ian R ^a   Ley, Steven V ^a   Ladlow, Mark ^b   Welch, Martin ^a   Spring, David R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b Uniqsis   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FLOW SYNTHESIS; QUINOLONES; STRUCTURAL ANALOGUE;

QUINOLONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; PSEUDOMONAS AERUGINOSA; SYNTHESIS;

MICROWAVES; MOLECULAR STRUCTURE; PSEUDOMONAS AERUGINOSA; QUINOLONES;

PSEUDOMONAS;

EID: 78650129282     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00652a     Document Type: Article

References (45)

1. W. C. Fuqua S. C. Winans E. P. Greenberg J. Bacteriol. 1994 176 269 275
2. B. L. Bassler R. Losick Cell 2006 125 237 246
3. C. Fuqua M. R. Parsek E. P. Greenberg Annu. Rev. Genet. 2001 35 439
4. M. Welch H. Mikkelsen J. E. Swatton D. S. Smith G. L. Thomas F. G. Glansdorp D. R. Spring Mol. BioSyst. 2005 1 196 202
5. D. Smith J.-H. Wang J. E. Swatton P. Davenport B. Price H. Mikkelsen H. Stickland K. Nishikawa N. Gardiol D. R. Spring M. Welch Sci. Prog. 2006 89 167 211
6. T. B. Rasmussen M. Givskov Microbiology 2006 152 895 904
7. M. Hentzer M. Givskov J. Clin. Invest. 2003 112 1300 1307
8. F. A. A. Amer E. M. El-Behedy H. A. Mohtady Biotechnol. Molec. Biol. Rev. 2008 3 46 57
9. H. Suga K. M. Smith Curr. Opin. Chem. Biol. 2003 7 586 591
10. S. Everts, in Chem. Eng. News, 2006, 84 (43), pp. 17-26
11. For recent discussions see: M. E. Pomianek M. F. Semmelhack ACS Chem. Biol. 2007 2 293 295
12. N. Ni M. Li J. Wang B. Wang Med. Res. Rev. 2009 29 65 124
13. S. R. Chhabra C. Harty D. S. W. Hooi M. Daykin P. Williams G. Telford D. I. Pritchard B. W. Bycroft J. Med. Chem. 2003 46 97 104
14. T. Hjelmgaard T. Persson T. B. Rasmussen M. Givskov J. Nielsen Bioorg. Med. Chem. 2003 11 3261 3271
15. G. D. Geske J. C. O'Neil D. M. Miller M. E. Mattmann H. E. Blackwell J. Am. Chem. Soc. 2007 129 13613 13625
16. E. C. Pesci J. B. J. Milbank J. P. Pearson S. McKnight A. S. Kende E. P. Greenberg B. H. Iglewski Proc. Natl. Acad. Sci. U. S. A. 1999 96 11229 11234
17. For a recent discussion of PQS-mediated quorum sensing see: J. F. Dubern S. P. Diggle Mol. BioSyst. 2008 4 882 888
18. R. Popat S. A. Crusz S. P. Diggle Br. Med. Bull. 2008 87 63 75
19. E. Deziel S. Gopalan A. P. Tampakaki F. Lepine K. E. Padfield M. Saucier G. Xiao L. G. Rahme Mol. Microbiol. 2004 55 998 1014
20. S. P. Diggle K. Winzer S. R. Chhabra K. E. Worrall M. Camara P. Williams Mol. Microbiol. 2003 50 29 43
21. L. A. Gallagher S. L. McKnight M. S. Kuznetsova E. C. Pesci C. Manoil J. Bacteriol. 2002 184 6472 6480 See also ref. 5
22. D. N. Collier L. Anderson S. L. McKnight T. L. Noah M. Knowles R. Boucher U. Schwab P. Gilligan E. C. Pesci FEMS Microbiol. Lett. 2002 215 41 46
23. J. Hodgkinson S. D. Bowden W. R. J. D. Galloway D. R. Spring M. Welch J. Bacteriol. 2010 192 3833 3837
24. For recent selected examples of modulating AHL-mediated quroum sensing systems see: G. D. Geske J. C. O'Neill H. E. Blackwell Chem. Soc. Rev. 2008 37 1432 1447 and references therein
25. G. L. Thomas C. M. Bohner H. E. Williams C. M. Walsh M. Ladlow C. E. Byrant D. R. Spring Mol. BioSyst. 2006 2 132 137
26. K. Tateda Y. Ishii M. Horikawa T. Matsumoto S. Miyairi J. C. Pechere T. J. Standiford M. Ishiguro K. Yamaguchi Infect. Immun. 2003 71 5785 5793
27. For selected examples of limited SAR studies on such molecules in the context of quorum sensing systems see: S. P. Diggle K. Winzer S. R. Chhabra K E. Worall M. Camara P. Williams Mol. Microbiol. 2003 50 29 43
28. E. C. Pesci J. B. Milbank J. P. Pearson S. McKnight A. S. Kende E. P. Greenberg B. H. Iglewski Proc. Natl. Acad. Sci. U. S. A. 1999 96 11229 11234
29. Pesci et al. demonstrated that 3-heptyl-2-hydroxy-4(1H)-quinolone (in which the heptyl- and hydroxyl subsitutents have been switched positions relative to PQS) and 2-heptyl-4-hydroxyquinoline N-oxide (a PQS isomer which lacks the 3-hydroxy group) do not exhibit any biological activity comparable to that of PQS. In addition, Diggle et al. demonstrated that both 2-heptyl-4(1H)-quinolone and 3-formyl-2-heptyl-4(1H)-quinolone were biologically inactive in this context.
30. For example, Pritchard and co-workers have reported a 3-step synthesis of HHQ from octanoic acid which proceeds in an overall yield of ∼ 48%: D. I. Pritchard, B. W. Bycroft, S. R. Chhabra and D. Hooi. Substitued 4-quinolones. PCT Int. Appl. WO/2002/047686, 2002
31. P. Hradil J. Hlavac K. Lemr J. Heterocycl. Chem. 1999 36 141 144
32. A similar method for synthesising PQS (via the synthesis and isolation of intermediate (4) has been disclosed: I. C. Purcell, Bacterial Autoinducer Derived 4-Quinolones as Novel Immune Modulators. PhD thesis, 2007, University of Nottingham, UK. Purcell also describes the synthesis of 5 different 3-hydroxy-4(1H)-quinolone derivatives several 2-alkyl substituted PQS derivatives
33. R. Tillyer L. F. Frey D. M. Tschaen U. H. Dolling Synlett 1996 225
34. P. Hradil M. Grepl J. Hlavac M. Soural M. Malon V. Bertolasi J. Org. Chem. 2006 71 819 822
35. 1H NMR analysis. Further purification, if required, can be achieved by recrystallisation from ethyl acetate.
36. The synthesis of PQS achieved using the route outlined in Scheme 1 has been reported to proceed in an overall yield of ∼ 13% from commercial starting materials (see ref. 12a and ref. 13).
37. G. P. Xiao J. X. He L. G. Rahme Microbiology 2006 152 1679 1686
38. C. Cugini M. W. Calfee J. M. Farrow D. K. Morales E. C. Pesci D. A. Hogan Mol. Microbiol. 2007 65 896 906
39. F. Dubern S. P. Diggle Mol. BioSyst. 2008 4 882 888
40. The analysis of the results assumes that the activity is due to protein binding rather than cell permeability and other transport properties
41. See:http://www.uniqsis.com/ (accessed 11th August 2010).
42. Recent papers using the Uniqsis FlowSyn continuous flow reactor include: A. Palmieri S. V. Ley A. Polyzos M. Ladlow I. R. Baxendale Beilstein J. Org. Chem. 2009 5 10.3762/bjoc.5.23
43. A. Palmieri S. V. Ley K. Hammond A. Polyzos I. R. Baxendale Tetrahedron Lett. 2009 50 3287 3289
44. C. F. Carter I. R. Baxendale J. B. J. Pavey S. V. Ley Org. Biomol. Chem. 2010 8 1588 1595
45. The synthesis of PQS analogue 10d was also achieved in-flow (see ESI).