2. Academic Validation
  3. Montmorillonite K-10 catalyzed cyclization of N-ethoxycarbonyl-N'-arylguanidines: access to pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole derivatives

Montmorillonite K-10 catalyzed cyclization of N-ethoxycarbonyl-N'-arylguanidines: access to pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole derivatives

  • Bioorg Med Chem Lett. 2010 Jul 15;20(14):4244-7. doi: 10.1016/j.bmcl.2010.05.028.
Julien Debray 1,  Walid Zeghida,  Brigitte Baldeyrou,  Christine Mahieu,  Amélie Lansiaux,  Martine Demeunynck
Affiliations

Affiliation

  • 1 Département de Chimie Moléculaire, UMR-5250 and ICMG FR-2607, CNRS-Université Joseph Fourier, BP 53, 38041 Grenoble cedex 9, France.
PMID: 20570510 DOI: 10.1016/j.bmcl.2010.05.028
Abstract

Two new heterocycles, pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole, were prepared in three steps from 3-aminocarbazole and 3-aminoindole, respectively. The key Friedel-Crafts intramolecular cyclization was realized under microwave irradiation using montmorillonite K-10 clay as a catalyst. The pyrimido[4,5-c]carbazole derivative shows significant micromolar IC(50) against Cancer cell lines. Unlike similar carbazole and indolocarbazole compounds, the molecule does not interfere with Topoisomerase activity.

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