Download PDF
Synthesis 2001(11): 1693-1703
DOI: 10.1055/s-2001-16763
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Bis-indolic Macrolactams

Jacques Hénin, Eric Noé, Jean-Yves Laronze*
Laboratoire de Chimie Thérapeutique, UMR-CNRS 6013, IFR n°53 Biomolécules, UFR de Pharmacie, 3 Avenue du Maréchal Juin, 51096 Reims Cedex, France
Fax: +33(3)26918029; e-Mail: jy.laronze@univ-reims.fr;
Further Information

Publication History

Received 19 February 2001
Publication Date:
12 August 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

Treatment of several ω-halogenoamides, derived from tryptamine, with powdered potassium hydroxide in 1,2-dimethoxyethane in the presence of 18-crown-6, resulted in intramolecular and/or bimolecular cyclization, depending on the length of the chain and dilution conditions, to give macrocyclic compounds. Some of them were converted by a Bischler-Napieralski reaction, followed or not by reduction, to new tetracyclic derivatives of β-carbolines.

Key words

indoles - macrocycles - crown ether - β-carbolines - high dilution

    References

  • 1 Gutte B. Peptides. Syntheses, Structures and Applications   Academic Press; New York: 1995. 
  • 2 Diker K. Thése   Université de Reims Champagne-Ardenne; Reims: 1996. 
  • 3 Sigaut F. Didierdefresse B. Lévy J. Tetrahedron  2000,  56:  9641 
    CrossrefSearch in Google Scholar
  • 4 Charlet-Fagnere C. Laronze J. Laronze JY. Toupet L. Vistelle R. Lamiable D. Mouchard C. Renard P. Adam G. Bull. Soc. Chim. Fr.  1996,  39 
  • 5 Charlet-Fagnère C. Jiang W.-Q. Laronze JY. Tetrahedron Lett.  1999,  40:  1685 
    CrossrefSearch in Google Scholar
  • 6 Hénin J. Noé E. Laronze JY. Pfeiffer B. Renard P. Guardiola-Lemaître B. Delagrange P. Pharmaceutical Sciences  1997,  3:  289 
    Search in Google Scholar
  • 7 Castelhano AL. Billedeau R. Dewdney N. Donnelly S. Horne S. Kurz LJ. Liak TJ. Martin R. Uppington R. Yuan Z. Krantz A. Bioorg. Med. Chem. Lett.  1995,  5:  1415 
    CrossrefSearch in Google Scholar
  • 8a Castelhano AL, Liak TJ, Horne S, Krantz A, and Yuan Z. inventors; US Patent  6013792. 
  • 9 Atta-Ur-Rahman; Yousuf T. Pakistan J. Sci. Ind. Res.  1973,  16:  100 
    Search in Google Scholar
  • 10 Nagarajan K. Weissmann Ch. Schmid H. Karrer P. Helv. Chim. Acta  1963,  46:  1221 
    Search in Google Scholar
  • 11 Costerousse G. Buendia J. Toromanoff E. Martel J. Bull. Soc. Chim. Fr.  1978,  355 
  • 12 Dietrich B. Lehn JM. Sauvage JP. Blauzat J. Tetrahedron  1973,  29:  1629 
    CrossrefSearch in Google Scholar