Synthesis and characterization of new acridone glucosides

FASCIO MIRTA. L.; D'ACCORSO NORMA B.; DOCAMPO PALACIOS MAITE; PELLÓN ROLANDO F.

Palermo - Italia

Congreso; 20th International Congress of Heterocyclic Chemistry; 2005

International Heterocyclic Chemistry Society

Synthesis and characterization of new acridone glucosides 1Mirta Liliana Fascio, Norma Beatriz D´Accorso, 2Maite Docampo Palacios and Rolando Fermín Pellón.   1CIHIDECAR-CONICET. Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, UBA, Ciudad Universitaria, Pabellón II, Buenos Aires, Argentina. 2Centro de Química Farmacéutica, apartado 16042, La Habana, Cuba. 1CIHIDECAR-CONICET. Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, UBA, Ciudad Universitaria, Pabellón II, Buenos Aires, Argentina. 2Centro de Química Farmacéutica, apartado 16042, La Habana, Cuba. norma@qo.fcen.uba.ar In the last years some acridone derivatives have been reported as anti-multidrug resistant (1), anti-cancer activities (2) and telomerase inhibitors (3) between others. Due to the important properties these sorts of compounds present and their potential applicability, we decide to synthesize new N-substituted acridones. We have already reported the synthesis of N-allyl and N-propardienylacridones using phase-transfer catalysis (4). Following the synthetic pathway, we apply 1,3-dipolar cycloaddition techniques to obtain some novel acridone glucosides 3 from the corresponding N-allyl derivatives 2. In this work, we describe the characterization of these new compounds.                                                                                                                                                                                                                                                                                                                                                      (1)     Hegde , R.; Thimmaiah, P.; Yerigeri , M. C.; Krishnegowda, G.; Thimmaiah, K. N. ; Houghton,  P. J.  Eur. J. Med. Chem.  2004, 39, 161–177. (2)     White, L. K.; Wright, W. E.; Shay, J. W. Trends Biotechnol. 2001, 19, 114-120; Mergny, J. L.; Riou, J. F.; Maillet, P.; Teulade-Fichou, M.  P.; Gilson, E. Nucl. Acids Res. 2002, 30, 839-865; Neidle, S.; Parkinson, G. N. Nat. Rev. Drug Discovery 2002 , 1, 383-393;   (3)     Harrison, R. J.; Reszka, A. P.; Haider, S. M.; Romagnoli, B.; Morrell, J.; Read, M. A.; Gowan, S. M.; Incles, C. M.;.Kelland, L. R.; Neidle, S., Bioorg. Med. Chem. Lett. 2004, 14, 5845–5849. (4)     Xuárez, L.; Pellón, R. F.; Fascio, M. ; Montesano, V.; D´Accorso, N., Heterocycles 2004, 63, 23-28.