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Synthesis 2008(18): 2891-2898  
DOI: 10.1055/s-2008-1067217
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel and Efficient Method for the Synthesis of Unsymmetrical Diindolylmethanes and Heterocyclic(indolyl)alkanes

Mohit L. Deb, Pulak J. Bhuyan*
Medicinal Chemistry Division, North East Institute of Science & Technology (Formerly RRL), Jorhat 785006, Assam, India
Fax: +91(376)2370011; e-Mail: pulak_jyoti@yahoo.com;
Further Information

Publication History

Received 2 April 2008
Publication Date:
06 August 2008 (online)

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Abstract

3-Alkylated indoles, obtained from a three-component reaction of indole, aldehyde, and N,N-dimethylbarbituric acid, undergo an elimination-addition reaction with another indole molecule or heterocyclic nucleophile giving unsymmetrical diindolylmethanes or heterocyclic(indolyl)alkanes in the absence of a catalyst.

Key words

unsymmetrical diindolylmethanes - indole - 3-alkylated indole - anticancer

    References

  • 1a Bradfield CA. Bjeldanes LF. J. Agric. Food Chem.  1987,  35:  46 
    Google Scholar
  • 1b Broadbent TA. Broadbent HS. Curr. Med. Chem.  1998,  5:  337 
    Google Scholar
  • 1c Broadbent TA. Broadbent HS. Curr. Med. Chem.  1998,  5:  469 
    Google Scholar
  • 2 Xue L. Pestka J. J. Li M. Firestone GL. Bjeldanes LF. J. Nutr. Biochem  2008,  19: 336
    Google Scholar
  • 3 Riby JE. Xue L. Chatterji U. Bjeldanes EL. Firestone GL. Bjeldanes LF. Mol. Pharmacol.  2006,  69:  430 
    Google Scholar
  • 4 Dalessandri KM. Firestone GL. Fitch MD. Bradlow HL. Bjeldanes LF. Nutr. Cancer.  2004,  50:  161 
    CrossrefPubMedGoogle Scholar
  • 5 Hong C. Firestone GL. Bjeldanes LF. Biochem. Pharmacol.  2002,  50:  161 
    Google Scholar
  • 6 Le HT. Schaldach CM. Firestone GL. Bjeldanes LF. J. Biol. Chem.  2003,  278:  21136 
    CrossrefGoogle Scholar
  • 7 Deng J. Sanchez T. Neamati N. Briggs JM. J. Med. Chem.  2006,  49:  1684 
    CrossrefPubMedGoogle Scholar
  • 8 Bell R. Carmeli S. Sar N. J. Nat. Prod.  1994,  57:  1587 
    CrossrefPubMedGoogle Scholar
  • 9 Ling J, and Wan-Ru C. inventors; US  68,00,655. 
  • 10a Lézé M.-P. Le Borgne M. Marchand P. Loquet D. Kogler M. Le Baut G. Palusczak A. Hartmann RW. J. Enzym. Inhib. Med. Chem.  2004,  19:  549 
    Google Scholar
  • 10b Le Borgne M. Marchand P. Delevoye-Seiller B. Robert J.-M. Le Baut G. Hartmann RW. Palzer M. Bioorg. Med. Chem. Lett.  1999,  9:  333 
    Google Scholar
  • 11a Yadav JS. Reddy BVS. Satheesh G. Prabhakar A. Kunwar AC. Tetrahedron Lett.  2003,  44:  2221 
    Google Scholar
  • 11b Bandgar BP. Shaikh KA. Tetrahedron Lett.  2003,  44:  1959 
    Google Scholar
  • 11c Ji S.-J. Wang S.-Y. Zhang Y. Loh T.-P. Tetrahedron  2004,  60:  2051 
    Google Scholar
  • 11d Koshima H. Matsuaka W. J. Heterocycl. Chem.  2002,  39:  1089 
    Google Scholar
  • 11e Chakrabarty M. Ghosh N. Basak R. Harigaya Y. Tetrahedron Lett.  2002,  43:  4075 
    Google Scholar
  • 11f Yadav JS. Reddy BVS. Satheesh G. Tetrahedron Lett.  2004,  45:  3673 
    Google Scholar
  • 11g Azizi N. Torkian L. Saidi MR. J. Mol. Catal. A: Chem.  2007,  275:  109 
    Google Scholar
  • 11h Karthik M. Magesh CJ. Perumal PT. Palanichamy M. Arabindoo B. Murugesan V. Appl. Catal., A  2005,  286:  137 
    Google Scholar
  • 11i Gu D.-G. Ji S.-J. Jiang Z.-Q. Zhou M.-F. Loh T.-P. Synlett  2005,  959 
    Google Scholar
  • 12a Denis J.-N. Mauger H. Vallee Y. Tetrahedron Lett.  1997,  38:  8515 
    Google Scholar
  • 12b Chakrabarty M. Basak R. Ghosh N. Tetrahedron Lett.  2001,  42:  3913 
    Google Scholar
  • 13 Zeng X.-F. Ji S.-J. Wang S.-Y. Tetrahedron  2005,  61:  10235 
    CrossrefGoogle Scholar
  • 14 Herran GDL. Segura A. Csaky AG. Org. Lett.  2007,  9:  961 
    CrossrefPubMedGoogle Scholar
  • 15 Deb ML. Bhuyan PJ. Tetrahedron Lett.  2007,  48:  2159 
    CrossrefGoogle Scholar