Montmorillonite K-10 catalyzed cyclization of N-ethoxycarbonyl-N'-arylguanidines: access to pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole derivatives.
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.
Debray
Julien
J
Département de Chimie Moléculaire, UMR-5250 and ICMG FR-2607, CNRS-Université Joseph Fourier, BP 53, 38041 Grenoble cedex 9, France.
Zeghida
Walid
W
Baldeyrou
Brigitte
B
Mahieu
Christine
C
Lansiaux
Amélie
A
Demeunynck
Martine
M
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*
D002227:Carbazoles; D006146:Guanidines; D007211:Indoles; C503188:montmorillonite K-10; D001546:Bentonite