Download PDF
Synthesis 2009(22): 3819-3822  
DOI: 10.1055/s-0029-1217007
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1,11-Dihydro-2H-[1,3]oxazolo[4′,5′:5,6]indeno[1,2-b]quinolin-2-ones with Potential Topoisomerase I Inhibitory Activity

Marc Delota, Pascal Carato*a, Christophe Furman*b, Amélie Lemoineb, Nicolas Lebeguea, Pascal Berthelota, Saïd Yousa
a Faculté de Pharmacie, Laboratoire de Chimie Thérapeutique (EA 1043), Université Lille Nord de France, 3 rue du Professeur Laguesse, BP 83, 59006 Lille Cedex, France
b Institut de Chimie Pharmaceutique Albert Lespagnol (EA 2692), IFR 114, Université Lille Nord de France, 3 rue du Professeur Laguesse, BP 83, 59006 Lille Cedex, France
Fax: +3(33)20964913; e-Mail: pascal.carato@univ-lille2.fr;
Further Information

Publication History

Received 24 June 2009
Publication Date:
23 September 2009 (online)

    Permissions and Reprints All articles of this category

Corrected by:

Synthesis of 1,11-Dihydro-2H-[1,3]oxazolo[4′,5′:5,6]indeno[1,2-b]quinolin-2-ones with Potential Topoisomerase I Inhibitory ActivitySynthesis 2010; 2010(01): 180-180
DOI: 10.1055/s-0029-1218605

Abstract

A series of 1,11-dihydro-2H-[1,3]oxazolo[4′,5′:5,6]indeno[1,2-b]quinolin-2-ones were prepared by means of Friedländer condensations. The starting materials for the preparations were commercial substituted-2-aminoacetophenones and various 5,6-dihydro-2H-indeno[5,6-d][1,3]oxazole-2,7(3H)-diones that were synthesized from 2(3H)-benzoxazolones or their N-methyl analogues.

Key words

alkaloids - heterocycles - cyclizations - condensation - fused-ring systems

    References

  • 1 Dallavalle S. Merlini L. In Modern Alkaloids   Fattorusso E. Tagliatatela O. Wiley-VCH; Weinheim: 2008.  p.503 
    Google Scholar
  • 2 Wall ME. Wani MC. Cooke CE. Palmer KT. McPhail AT. Sim GA. J. Am. Chem. Soc.  1966,  88:  3888 
    CrossrefGoogle Scholar
  • 3 Hsiang YH. Hertzberg R. Hetch SM. Liu LF. J. Biol. Chem.  1985,  260:  14873 
    Google Scholar
  • 5 Moertel CG. Schutt AJ. Reitemeier RJ. Hahn RG. Cancer Chemother. Rep.  1972,  56:  649 
    Google Scholar
  • 6 Feng W. Satyanarayana M. Tsai Y.-c. Liu AA. Liu LF. LaVoie EJ. Bioorg. Med. Chem. Lett.  2008,  18:  3570 
    CrossrefGoogle Scholar
  • 7 Nacro K. Zha C. Guzzo PR. Herr RJ. Peacec D. Friedrichc TD. Bioorg. Med. Chem.  2007,  15:  4237 
    CrossrefGoogle Scholar
  • 8 Cheng Y. An LK. Wu N. Wang XD. Bu XZ. Huang ZS. Gu LQ. Bioorg. Med. Chem.  2008,  16:  4617 
    CrossrefGoogle Scholar
  • 9 Poupaert JH. Kanyonyo M. Ucar H. Mouithys AM. Diouf O. Lesieur D. Bull. Soc. Chim. Belg.  1996,  105:  397 
    Google Scholar
  • 10 Aichaoui H. Poupaert JH. Lesieur D. Henichart JP. Bull. Soc. Chim. Belg.  1992,  101:  1053 
    Google Scholar
  • 11 Merdji B. Lesieur D. Lespagnol C. Barbry D. Couturier D. J. Heterocycl. Chem.  1981,  18:  1223 
    CrossrefGoogle Scholar
  • 12 Aichaoui H. Lesieur D. Henichart JP. J. Heterocycl. Chem.  1992,  29:  171 
    CrossrefGoogle Scholar
  • 13 Aichaoui H. Poupaert JH. Lesieur D. Henichart JP. Tetrahedron  1991,  47:  6649 
    CrossrefGoogle Scholar
  • 14 Moussavi Z. Lesieur D. Lespagnol C. Sauzières J. Olivier P. Eur. J. Med. Chem.  1989,  24:  55 
    CrossrefGoogle Scholar
  • 15 Depreux P. Aichaoui H. Lesieur I. Heterocycles  1993,  36:  1051 
    CrossrefGoogle Scholar
  • 16 Merdji B. Lesieur D. Lespagnol C. Barbry D. Couturier D. J. Heterocycl. Chem.  1981,  18:  1223 
    CrossrefGoogle Scholar
  • 17 Park CH. Siomboing X. Yous S. Gressier B. Luyckx M. Chavatte P. Eur. J. Med. Chem.  2002,  37:  461 
    CrossrefGoogle Scholar
  • 18 Chackal S. Houssin R. Henichart JP. J. Org. Chem.  2002,  67:  3502 
    CrossrefGoogle Scholar
4

Special issue: The Camptothecins: Unfolding Their Anticancer Potential, Ann. N. Y. Acad. Sci. 2000, 922, 1