PDF icon PDF herunterladen
Synlett 2009(15): 2487-2491  
DOI: 10.1055/s-0029-1217745
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Tetramic Acids as Scaffolds: Synthesis, Tautomeric and Antibacterial Behaviour

Yong-Chul Jeong, Mark G. Moloney*
Chemistry Research Laboratory, University of Oxford, Mansfield Road, OX1 3TA, UK
Fax: +44(1865)275002; e-Mail: mark.moloney@chem.ox.ac.uk;
Weitere Informationen

Publikationsverlauf

Received 26 May 2009
Publikationsdatum:
27. August 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

Efficient synthetic routes for tetramic acids variously substituted on the ring nitrogen, their tautomeric behaviour in solution and their antibiotic activity are reported.

Key words

heterocycles - tautomerism - natural products - drugs

    References

  • 1a Gänzle MG. Appl. Microbiol. Biotechnol.  2004,  64:  326 
    Suche in Google Scholar
  • 1b Sadar MD. Williams DE. Mawji NR. Patrick BO. Wikanta T. Chasanah E. Irianto HE. Soest RV. Andersen RJ. Org. Lett.  2008,  10:  4947 
    Suche in Google Scholar
  • 1c Pattenden G. Rescourio G. Org. Biomol. Chem.  2008,  6:  3428 
    Suche in Google Scholar
  • 1d Bagwell CL. Moloney MG. Thompson AL. Bioorg. Med. Chem. Lett.  2008,  18:  4081 
    Suche in Google Scholar
  • 1e Moloney MG. Trippier PC. Yaqoob M. Wang Z. Curr. Drug Discovery Technol.  2004,  1:  181 
    Suche in Google Scholar
  • 1f Jeong Y.-C. Hwang SK. Ahn K.-H. Bull. Korean Chem. Soc.  2005,  26:  826 
    Suche in Google Scholar
  • 1g Giordano A. Monica CD. Landi F. Spinella A. Sodano G. Tetrahedron Lett.  2000,  41:  3979 
    Suche in Google Scholar
  • 2a Royles BJL. Chem. Rev.  1995,  95:  1981 
    Suche in Google Scholar
  • 2b Schobert R. Schlenk A. Bioorg. Med. Chem.  2008,  16:  4203 
    Suche in Google Scholar
  • 3a Mulholland TPC. Foster R. Haydock DB. J. Chem. Soc., Perkin Trans. 1  1972,  2121 
  • 3b Lowe G. Yeung HW. J. Chem. Soc., Perkin Trans. 1  1973,  2907 
  • 3c Heinicke GW. Morella AM. Orban J. Prager RH. Ward AD. Aust. J. Chem.  1985,  38:  1847 
    Suche in Google Scholar
  • 3d Page PCB. Hamza AS. Leach DC. Allin SM. Andrews DM. Rassias GA. Org. Lett.  2003,  5:  353 
    Suche in Google Scholar
  • 3e Park TH. Paik S. Lee SH. Bull. Korean Chem. Soc.  2003,  24:  1227 
    Suche in Google Scholar
  • 3f Spatz JH. Welsch SJ. Duhaut D.-E. Jäger N. Boursier T. Fredrich M. Allmendinger L. Ross G. Kolb J. Burdack C. Umkehrer M. Tetrahedron Lett.  2009,  50:  1705 
    Suche in Google Scholar
  • 3g Andrews MD. Brewster A. Moloney MG. Tetrahedron: Asymmetry  1994,  5:  1477 
    Suche in Google Scholar
  • 3h Andrews MD. Brewster AG. Crapnell KM. Ibbett AJ. Jones T. Moloney MG. Prout K. Watkin D. J. Chem. Soc., Perkin Trans. 1  1998,  223 
  • 3i Jones RCF. Begley MJ. Peterson GE. Sumaria S. J. Chem. Soc., Perkin Trans. 1  1990,  1959 
  • 4a Marquardt U. Schmid D. Jung G. Synlett  2000,  1131 
  • 4b Li W.-R. Lin ST. Hsu N.-M. Chern M.-S. J. Org. Chem.  2002,  67:  4702 
    Suche in Google Scholar
  • 4c Hosseini M. Kringelum H. Myrray A. Tønder JE. Org. Lett.  2006,  8:  2103 
    Suche in Google Scholar
  • 4d Pirc S. Bevk D. Jakše R. Rečnik S. Golič L. Golobič A. Meden A. Stanovnik B. Svete J. Synthesis  2005,  2969 
  • 4e Liu Z. Ruan X. Huang X. Bioorg. Med. Chem. Lett.  2003,  13:  2505 
    Suche in Google Scholar
  • 5a Schobert R. Dietrich M. Mullen G. Urbina-Gonzalez J.-M. Synthesis  2006,  3902 
  • 5b Fustero S. Torre MG. Sanz-Cervera JF. Arellano CR. Piera J. Simon A. Org. Lett.  2002,  4:  3651 
    Suche in Google Scholar
  • 6a Lacey RN. J. Chem. Soc.  1954,  850 
  • 6b Harris SA. Fisher LV. Folkers K. J. Med. Chem.  1965,  8:  478 
    Suche in Google Scholar
  • 6c Yuki H. Tohira Y. Aoki B. Kano T. Takama S. Yamazaki T. Chem. Pharm. Bull.  1967,  15:  1107 
    Suche in Google Scholar
  • 6d Romoff TT. Ma L. Wang Y. Campbell DA. Synlett  1998,  1341 
  • 6e Jones RCF. Pillainayagam TA. Synlett  2004,  2815 
  • 6f Steyn PS. Wessels PL. Tetrahedron Lett.  1978,  4707 
  • 6g Yendapally R. Hurdle JG. Carson EI. Lee RB. Lee RE. J. Med. Chem.  2008,  51:  1487 
    Suche in Google Scholar
  • 7a Baldwin JE. Coates JB. Halpern JB. Moloney MG. Pratt AJ. Biochem. J.  1989,  261:  197 
    Suche in Google Scholar
  • 7b Baldwin JE. Coates JB. Moloney MG. Pratt AJ. Willis AC. Biochem. J.  1989,  266:  561 
    Suche in Google Scholar
  • 7c Miller AK. Celozzi E. Pelak BA. Stapley EO. Hendlin D. Antimicrob. Agents Chemother.  1972,  2:  281 
    Suche in Google Scholar
  • 8a Burmeister HR. Ellis JJ. Hesseltine CW. Appl. Microbiol.  1972,  23:  1165 
    Suche in Google Scholar
  • 8b Burmeister HR. Bennett GA. Vesonder RF. Hesseltine CW. Antimicrob. Agents Chemother.  1974,  5:  634 
    Suche in Google Scholar