Università degli Studi di Milano   Archivio Istituzionale della Ricerca
Please use this identifier to cite or link to this item: http://hdl.handle.net/2434/207074

Title: Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline
Authors: SPARATORE, ANNA CONCETTINA (Last author)
BARTESELLI, ANNA (Second author)
BASILICO, NICOLETTA
PARAPINI, SILVIA
TARAMELLI, DONATELLA (Second to last author)
CASAGRANDE, MANOLO (First author)
Abstract: With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC(50)<30nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents.
Keywords: Antimalarial agents ; 4-aminoquinoline derivatives ; chloroquine ; Plasmodium falciparum
MIUR subjects: CHIM/08 - Chimica Farmaceutica
MED/04 - Patologia Generale
Publication date: 2-Aug-2012
Digital Object Identifier (DOI): 10.1016/j.bmc.2012.07.040
Citation: Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline / M. Casagrande, A. Barteselli, N. Basilico, S. Parapini, D. Taramelli, A. Sparatore. - In: Bioorganic & medicinal chemistry. - ISSN 0968-0896. - ISSN 1464-3391. - 20:19(2012 Aug 02), pp. 5965-5979.
Pubmed identifier: 22917857
ISI identifier: 000309059000027
Scopus identifier: 84866360704
Type: Article (author)

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