Sci Pharm; 2009; 77: 725–741
Synthesis of [(7-Chloroquinolin-4-yl)amino]chalcones: Potential Antimalarial and Anticancer Agents
Rosa FERRER 1, Gricela LOBO 1, Neira GAMBOA 2, Juan RODRIGUES 2,3, Claudia ABRAMJUK 3, Klaus JUNG 3, Michael LEIN 3,4, Jaime E. CHARRIS * 1
1 Laboratorio de Síntesis Orgánica, Facultad de Farmacia, Universidad Central de Venezuela, Apartado 47206, Los Chaguaramos, 1041-A Caracas, Venezuela.
2 Laboratorio de Bioquímica, Facultad de Farmacia, Universidad Central de Venezuela, Apartado 47206, Los Chaguaramos, 1041-A Caracas, Venezuela.
3 Department of Urology, University Hospital Charité, Humboldt University, Berlin, Germany.
4 Berlin Institute for Urologic Research, Berlin, Germany.
* Corresponding author. E-mail: jaime.charris@ucv.ve (J. E. Charris)
Abstract
[(7-Chloroquinolin-4-yl)amino]chalcone derivatives derived from the corresponding 3- or 4-[(7-chloroquinolin-4-yl)amino]acetophenone were synthesized and evaluated for in vitro antimalarial and anticancer activity. The most active compounds 12, 13, 15, 17 and 19 from the 3-substituted series displayed inhibitory values against heme cristallization in the range of 93.14 ± 1.74 – 94.93 ± 1.50 % as an antimalarial mechanism and cytotoxic effect with IC50 values of 7.93 ± 2.05, 7.11 ± 2.06 and 6.95 ± 1.62 μg/mL for 13, 17 and 19 respectively against humane prostate LNCaP tumor cells.
Supporting Information
The scanned 13C NMR spectra of compounds 3, 4, 7–9, 13, 15, 16 and 19 are available: Supporting Information (Format: PDF, Seize: ca. 0.2 MB)
Keywords
Malaria • CQ • β-Hematin • Cancer • Prostate
Received May 11st, 2009 | Accepted October 15th, 2009 | Published Online October 16th, 2009
