title: Montmorillonite K-10 catalyzed cyclization of N-ethoxycarbonyl-N'-arylguanidines: access to pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole derivatives.
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.
authors.affiliation: Département de Chimie Moléculaire, UMR-5250 and ICMG FR-2607, CNRS-Université Joseph Fourier, BP 53, 38041 Grenoble cedex 9, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Debray
authors.forename: Walid
authors.initials: W
authors.lastname: Zeghida
authors.forename: Brigitte
authors.initials: B
authors.lastname: Baldeyrou
authors.forename: Christine
authors.initials: C
authors.lastname: Mahieu
authors.forename: Amélie
authors.initials: A
authors.lastname: Lansiaux
authors.forename: Martine
authors.initials: M
authors.lastname: Demeunynck
mesh_terms: D001546:Bentonite / Q000737:chemistry*; D002227:Carbazoles / Q000737:chemistry*; D002384:Catalysis; D045744:Cell Line, Tumor; D003500:Cyclization; D006146:Guanidines / Q000737:chemistry*; D006801:Humans; D007211:Indoles / Q000737:chemistry*
chemical_list: D002227:Carbazoles; D006146:Guanidines; D007211:Indoles; C503188:montmorillonite K-10; D001546:Bentonite