Download PDF
Synthesis 2010(24): 4312-4316  
DOI: 10.1055/s-0030-1258963
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 5-Amino-3-methylimidazolidine-2,4-dione and 1,3,5-Triazine Derivatives as Analogues of the Alkaloids Naamidine A and G

Helen M. Witcharda, Keith G. Watson*a,b
a Walter and Eliza Hall Institute of Medical Research, Biotechnology Centre, La Trobe R&D Park, Bundoora, 4 Research Avenue, Victoria 3086, Australia
Fax: +61(3)93452211; e-Mail: kwatson@wehi.edu.au;
b Department of Medical Biology, The University of Melbourne, Parkville, Victoria 3010, Australia
Further Information

Publication History

Received 17 September 2010
Publication Date:
09 November 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A simple two-step synthesis of 5-amino-3-methylimidazolidine-2,4-dione is described. Addition of this amine to cyanuric chloride followed by reaction with 4-methoxyphenol or 4-alkoxy­anilines gives analogues of the imidazole alkaloids naamidine A and G with a 1,3,5-triazine core.

Key words

antitumor agents - imidazolidine - naamidine alkaloids - nucleophilic addition - s-triazine

    References

  • 1a Sullivan JD. Giles RL. Looper RE. Curr. Bioact. Compd.  2009,  5:  39 
    Google Scholar
  • 1b Ralifo P. Crews P. J. Org. Chem.  2004,  69:  9025 
    Google Scholar
  • 2 Copp BR. Fairchild CR. Cornell L. Casazza AM. Robinson S. Ireland CM. J. Med. Chem.  1998,  41:  3909 
    CrossrefGoogle Scholar
  • 3 LaBarbera DV. Modzelewska K. Glazer AI. Gray PD. Kaur M. Liu T. Grossman D. Harper MK. Kuwada SK. Moghal N. Ireland CM. Anti-Cancer Drugs  2009,  20:  425 
    CrossrefGoogle Scholar
  • 4a Ohta S. Tsuno N. Nakamura S. Taguchi N. Yamashita M. Kawasaki I. Fujieda M. Heterocycles  2000,  53:  1939 
    Google Scholar
  • 4b Aberle NS. Lessene G. Watson KG. Org. Lett.  2006,  8:  419 
    Google Scholar
  • 5 Koswatta PB. Lovely CJ. Tetrahedron Lett.  2010,  51:  164 
    CrossrefGoogle Scholar
  • 6 Aberle NS. Catimel J. Nice EC. Watson KG. Bioorg. Med. Chem. Lett.  2007,  17:  3741 
    CrossrefGoogle Scholar
  • 7 Zheng M. Xu C. Ma J. Sun Y. Du F. Liu H. Lin L. Li C. Ding J. Chen K. Jiang H. Bioorg. Med. Chem.  2007,  15:  1815 
    CrossrefGoogle Scholar
  • 8 Biltz H. Robl R. Ber. Dtsch. Chem. Ges.  1921,  54:  2448 
    CrossrefGoogle Scholar
  • 9a Canellakis ES. Cohen PP. J. Biol. Chem.  1955,  213:  379 
    Google Scholar
  • 9b Piskala A. Gut J. Collect. Czech. Chem. Commun.  1961,  26:  2519 
    Google Scholar
  • 10 Nakamura S. Kawasaki I. Yamashita M. Ohta S. Heterocycles  2003,  60:  583 
    CrossrefGoogle Scholar
  • 11 Biltz H. Hanisch H. J. Prakt. Chem.  1926,  112:  138 
    CrossrefGoogle Scholar
  • 12 Sarges R. Schnur RC. Belletire JL. Peterson MJ. J. Med. Chem.  1988,  31:  230 
    CrossrefGoogle Scholar
  • 13 Moon H.-S. Jacobson EM. Khersonsky SM. Luzung MR. Walsh DP. Xiong W. Lee JW. Parikh PB. Lam JC. Kang T.-W. Rosania GR. Schier AF. Chang Y.-T. J. Am. Chem. Soc.  2002,  124:  11608 
    CrossrefGoogle Scholar
  • 14 Ienaga K. Nakamura K. Ishii A. Taga T. Miwa Y. Yoneda F. J. Chem. Soc., Perkin Trans. 1  1989,  1153 
    CrossrefGoogle Scholar
  • 15 Matsui M. Kamiya K. Shibata K. Muramatsu H. J. Org. Chem.  1990,  55:  1396 
    CrossrefGoogle Scholar