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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 23
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Original Articles

Synthesis of Berberine—Efflux Pump Inhibitor Hybrid Antibacterials

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Pages 3561-3568 | Received 11 Oct 2009, Published online: 05 Nov 2010

REFERENCES

  • Ball , A. R. ; Casadei , G. ; Samosorn , S. ; Bremner , J. B. ; Ausubel , F. M. ; Moy , T. I. ; Lewis , K. Conjugating berberine to a multidrug resistance pump inhibitor creates an effective antimicrobial . ACS Chem. Biol. 2006 , 1 , 594 – 600 .
  • German , N. ; Wei , P. ; Kaatz , G. W. ; Kerns , R. J. Synthesis and evaluation of fluoroquinolone derivatives as substrate based inhibitors of bacterial efflux pumps . Eur. J. Med. Chem. 2008 , 43 , 2453 – 2463 .
  • Barbachyn , M. R. Recent advances in the discovery of hybrid antibacterial agents: Annu. Rep. Med. Chem. Macor, J. E. (Ed.), Elsevier Academic Press, San Diego, 2008, 43, 281–290 .
  • Charifson , P. S. ; Grillot , A. L. ; Grossman , T. H. ; Parsons , J. D. ; Badia , M. ; Bellon , S. ; Deininger , D. D. ; Drumm , J. E. ; Gross , C. H. ; LeTiran , A. ; Liao , Y. ; Mani , N. ; Nicolau , D. P. ; Perola , E. ; Ronkin , S. ; Shannon , D. ; Swenson , L. L. ; Tang , Q. ; Tessier , P. R. ; Tian , S. K. ; Trudeau , M. ; Wang , T. ; Wei , Y. ; Zhang , H. ; Stamos , D. Novel dual-targeting benzimidazole urea inhibitors of DNA gyrase and topoisomerase IV possessing potent antibacterial activity: Intelligent design and evolution through the judicious use of structure-guided design and structure-activity relationships . J. Med. Chem. 2008 , 51 , 5243 – 5263 .
  • Tomkiewicz , D. ; Casadei , G. ; Larkins-Ford , J. ; Moy , T. I. ; Garner , J. ; Bremner , J. B. ; Ausubel , F. M. ; Lewis , K. ; Kelso , M. J. Berberine-INF55 (5-nitro-2-phenylindole) hybrid antimicrobials: Effects of varying the relative orientation of the berberine and INF55 components . Antimicrob. Agents Chemother. 2010 , 54 , 3219 – 3224 .
  • Bremner , J. B. ; Samosorn , S. 8-Allyldihydroberberine as an alternative precursor for the synthesis of 13-substituted berberine derivatives . Aust. J. Chem. 2003 , 56 , 871 – 873 .
  • Samosorn , S. ; Bremner , J. B. ; Ball , A. ; Lewis , K. Synthesis of functionalized 2-aryl-5-nitro-1H-indoles and their activity as bacterial NorA effux pump inhibitors . Bioorg. Med. Chem. 2006 , 14 , 857 – 865 .
  • Cacchi , S. ; Fabrazi , G. Synthesis and functionalization of indoles through palladium-catalyzed reactions . Chem. Rev. 2005 , 105 , 2873 – 2920 .
  • Leboho , T. C. ; Michael , J. P. ; van Otterloo , W. A. L. ; van Vuuren , S. F. ; de Koning , C. B. The synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles and their antibacterial and antifungal activity . Bioorg. Med. Chem. Lett. 2009 , 19 , 4948 – 4951 .
  • Wang , X. ; Lane , B. S. ; Sames , D. Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar-Rh(III) complexes assembled in situ . J. Am. Chem. Soc. 2005 , 127 , 4996 – 4997 .
  • Ambrus , J. I. ; Kelso , M. J. ; Bremner , J. B. ; Ball , A. R. ; Casadei , G. ; Lewis , K. Structure-activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus . Bioorg. Med. Chem. Lett. 2008 , 18 , 4294 – 4297 .
  • Noland , W. E. ; Rush , K. R. ; Smith , L. R. Nitration of indoles. IV. The nitration of 2-phenylindole . J. Org. Chem. 1966 , 31 , 65 – 69 .
  • Campo , M. A. ; Larock , R. C. Synthesis of fluoren-9-ones via palladium-catalyzed cyclocarbonylation of o-halobiaryls . Org. Lett. 2000 , 2 , 3675 – 3677 .

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