Probing the role of the covalent linkage of ferrocene into a chloroquine template.

Abstract

A new therapeutic approach to malaria led to the discovery of ferroquine (FQ, SR97276). To assess the importance of the linkage of the ferrocenyl group to a 4-aminoquinoline scaffold, two series of 4-aminoquinolines, structurally related to FQ, were synthesized. Evaluation of antimalarial activity, physicochemical parameters, and the beta-hematin inhibition property indicate that the ferrocene moiety has to be covalently flanked by a 4-aminoquinoline and an alkylamine. Current data reinforced our choice of FQ as a drug candidate.

• Authors: Christophe Biot, Wassim Daher, Cheikh M Ndiaye, Patricia Melnyk, Bruno Pradines, Natascha Chavain, Alain Pellet, Laurent Fraisse, Lydie Pelinski, Christian Jarry, Jacques Brocard, Jamal Khalife, Isabelle Forfar-Bares, Daniel Dive
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 49 Issue 15 Pg. 4707-14 (Jul 27 2006) ISSN: 0022-2623 [Print] United States
• PMID: 16854077 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Aminoquinolines
• Antimalarials
• Ferrous Compounds
• Hemeproteins
• Metallocenes
• Quinolines
• hemozoin
• Chloroquine
• ferroquine

Topics

• Aminoquinolines
• Animals
• Antimalarials (chemical synthesis, chemistry, pharmacology)
• Chloroquine (chemistry)
• Ferrous Compounds (chemical synthesis, chemistry, pharmacology)
• Hemeproteins (antagonists & inhibitors, chemical synthesis)
• Metallocenes
• Parasitic Sensitivity Tests
• Plasmodium falciparum (drug effects)
• Quinolines (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship