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Synthesis 2012(2): 215-218  
DOI: 10.1055/s-0031-1289644
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Parallel Synthesis of Aminobenzimidazole-Tethered Thiazoles

Sureshbabu Dadiboyenaa, Adel Nefzi*a,b
a Torrey Pines Institute for Molecular Studies, 11350 SW Village Parkway, Port St. Lucie, FL 34987, USA
Fax: +1(772)3453649; e-Mail: anefzi@tpims.org;
b Florida Atlantic University, Boca Raton, FL 33431, USA
Further Information

Publication History

Received 13 October 2011
Publication Date:
15 December 2011 (online)

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Abstract

A multistep approach to construct thiazole-derived aminobenzimidazoles from commercially available amino acids, amines, carboxylic acids, and α-halo ketones is described. Coupling of 9-fluorenylmethoxycarbonyl-protected (Fmoc-protected) amino acids to resin-bound aminobenzimidazoles provides essential intermediates for the construction of an array of thiazoles by utilizing the Hantzsch cyclization strategy. The aminobenzimidazole-tethered thiazoles were isolated in moderate yields.

Key words

solid-phase synthesis - aminobenzimidazoles - amino acids - thiazoles - heterocycles - Hantzsch cyclization

    References

  • 1 Ziegert RE. Torang J. Knepper K. Bräse S. J. Comb. Chem.  2005,  7:  147 
    Google Scholar
  • 2 Kundu B. Curr. Opin. Drug Discovery Dev.  2003,  6:  815 
    Google Scholar
  • 3 Feliu L. Vera-Luque P. Albericio F. Alvarez M. J. Comb. Chem.  2009,  11:  175 
    Google Scholar
  • 4 Franzen RG. J. Comb. Chem.  2000,  2:  195 
    Google Scholar
  • 5 Krchnak V. Holladay MW. Chem. Rev.  2002,  102 
    Google Scholar
  • 6 Ma W. Peterson B. Kelson A. Laborde E. J. Comb. Chem.  2009,  11:  697 
    Google Scholar
  • 7 Nicolau KC. Handbook of Combinatorial Chemistry   Wiley-VCH; Weinheim: 2002. 
    Google Scholar
  • 8 Combinatorial Chemistry and Molecular Diversity in Drug Discovery   Gordon EM. Kerwin JF. John Wiley & Sons; New York: 1998. 
    Google Scholar
  • 9 DeWitt SH. Czarnik AW. A Practical Guide to Combinatorial Chemistry   American Chemical Society; Washington DC: 1997. 
    Google Scholar
  • 10 Hoesl CE. Nefzi A. Houghten RA. J. Comb. Chem.  2003,  5:  155 
    Google Scholar
  • 11 Gallop MA. Barret RW. Dower WJ. Fodor SPA. Gordon EM. J. Med. Chem.  1994,  37:  1233 
    Google Scholar
  • 12 Dolle RE. Le Bourdoneec B. Morales GA. Moriarty KJ. Salvino JM. J. Comb. Chem.  2006,  8:  597 
    Google Scholar
  • 13 Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 
    Google Scholar
  • 14 Nefzi A. Ostresh JM. Yu J. Houghten RA. J. Org. Chem.  2004,  69:  3603 
    Google Scholar
  • 15 Gallop MA. Barret RW. Dower WJ. Fodor SPA. Gordon EM. J. Med. Chem.  1994,  37:  1385 
    Google Scholar
  • 16 Thompson LA. Ellman JA. Chem. Rev.  1996,  96:  555 
    Google Scholar
  • 17 Nefzi A. Marcello G. Truong L. Rattan S. Ostresh JM. Houghten RA. J. Comb. Chem.  2002,  4:  175 
    Google Scholar
  • 18 Soural M. Bouillon I. Krchňak V. J. Comb. Chem  2008,  10:  923 
    Google Scholar
  • 19 Brown HD. Matzuk AR. Ilves IR. Peterson LH. Harris SA. Sarett LH. Egerton JR. Yakstis JJ. Campbell WC. Cuckler AC. J. Am. Chem. Soc.  1961,  83:  1764 
    Google Scholar
  • 20 Craigo WA. LeSueur BW. Skibo EB. J. Med. Chem.  1999,  42:  3324 
    Google Scholar
  • 21 Wienen W. Hauel N. van Meel JC. Narr B. Ries U. Entzeroth M. Br. J. Pharmacol.  1993,  110:  245 
    Google Scholar
  • 22a Brown H. D. Matzuk A. R. Ilves IR. Peterson L. H. Harris S. A. Sarett L. H. Egerton J. R. Yakstis J. J. Campbell W. C. Cuckler A. C. J. Am. Chem. Soc.  1961,  83:  1764 
    Google Scholar
  • 22b Nakano H. Inoue T. Kawasaki N. Miyataka H. Matsumoto H. Taguchi T. Inagaki N. Nagai H. Satoh T. Chem. Pharm. Bull.  1999,  47:  1573 
    Google Scholar
  • 22c Dadiboyena S. Nefzi A. Tetrahedron Lett.  2011,  52:  7030 
    Google Scholar
  • 23 Acharya AN. Thai C. Ostresh JM. Houghten RA. J. Comb. Chem.  2002,  4:  496 
    Google Scholar
  • 24 Acharya AN. Ostresh JM. Houghten RA. Tetrahedron  2002,  58:  2095 
    Google Scholar
  • 25 Hoesl CE. Nefzi A. Houghten RA. J. Comb. Chem.  2004,  6:  220 
    Google Scholar
  • 26 Hoesl CE. Nefzi A. Houghten RA. Tetrahedron Lett.  2003,  44:  3705 
    Google Scholar
  • 27 Nefzi A. Giulianotti M. Houghten RA. Tetrahedron Lett.  2000,  41:  2283 
    Google Scholar
  • 28 Houghten RA. Proc. Natl. Acad. Sci. U.S.A.  1985,  82:  5131 
    Google Scholar
  • 29 Hantzsch AR. Weber JH. Ber. Dtsch. Chem. Ges.  1887,  20:  3118 
    Google Scholar
  • 30 Garcia-Egido E. Wong SYF. Warrington BH. Lab Chip  2002,  2:  31 
    Google Scholar
  • 31 Lin PY. Hou RS. Wang HM. Kang IJ. Chen LC. J. Chin. Chem. Soc.  2009,  56:  455 
    Google Scholar
  • 32 Kearney PC. Fernandez M. Flygare JA. J. Org. Chem.  1998,  63:  196 
    Google Scholar
  • 33 Arutyunyan S. Nefzi A. J. Comb. Chem.  2010,  12:  315 
    Google Scholar
  • 34 Jin Z. Nat. Prod. Rep.  2003,  20:  584 
    Google Scholar
  • 35 Bertram A. Blake AJ. de Turiso F. Hannam JS. Jolliffe KA. Pattenden G. Skae M. Tetrahedron  2003,  59:  6979 
    Google Scholar
  • 36 Jin Z. Nat. Prod. Rep.  2006,  23:  464 
    Google Scholar
  • 37 Vinicius M. Souza ND. J. Sulfur Chem.  2005,  26:  429 
    Google Scholar
  • 38 Rezanka T. Sobotka M. Spizek J. Sigler K. Anti-Infect. Agents Med. Chem.  2006,  5:  187 
    Google Scholar
  • 39 Sanfilippo PJ. Jetter MC. Cordova R. Noe RA. Chourmousis E. Lau CY. Wang E. J. Med. Chem.  1995,  38:  1057 
    Google Scholar
  • 40 Suzuki S. Yonezawa Y. Shin C. Chem. Lett.  2004,  33:  815 
    Google Scholar
  • 41 Kaiser ET. Colescott RL. Blossinger CD. Cook PI. Anal. Biochem.  1970,  34:  595 
    Google Scholar