To develop new classes of antimalarial agents, the possibility of replacing the phenolic ring of amodiaquine, tebuquine, and isoquine with other aromatic nuclei was investigated. Within a first set of pyrrole analogues, several compounds displayed high activity against both D10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. The isoquine structure was also modified by replacing the diethylamino group with more metabolically stable bicyclic moieties and by replacing the aromatic hydroxyl function with a chlorine atom. Among these compounds, two quinolizidinylmethylamino derivatives (6f and 7f) displayed high activity against both CQ-S and CQ-R strains.
Novel amodiaquine congeners as potent antimalarial agents / M. Casagrande, N. Basilico, S. Parapini, S. Romeo, D. Taramelli, A. Sparatore. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 16:14(2008 Jul 15), pp. 6813-6823. [10.1016/j.bmc.2008.05.068]
Novel amodiaquine congeners as potent antimalarial agents
M. CasagrandePrimo
;N. BasilicoSecondo
;S. Parapini;S. Romeo;D. TaramelliPenultimo
;A. SparatoreUltimo
2008
Abstract
To develop new classes of antimalarial agents, the possibility of replacing the phenolic ring of amodiaquine, tebuquine, and isoquine with other aromatic nuclei was investigated. Within a first set of pyrrole analogues, several compounds displayed high activity against both D10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. The isoquine structure was also modified by replacing the diethylamino group with more metabolically stable bicyclic moieties and by replacing the aromatic hydroxyl function with a chlorine atom. Among these compounds, two quinolizidinylmethylamino derivatives (6f and 7f) displayed high activity against both CQ-S and CQ-R strains.
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