Antimalarials based on the dioxane scaffold of plakortin. A concise synthesis and SAR studies.
In our search for new antimalarial agents inspired by natural products, we describe herein the synthesis, the evaluation of in vitro antiplasmodial activity, and the SAR studies for a series of endoperoxide antimalarials based on the plakortin scaffold. These simplified analogues are characterized by: (i) a 3,6-dihydro-1,2-dioxin ring or a 1,2-dioxane ring disubstituted at C-4 and C-5; (ii) a pentyl substituent at C-6 ('western' alkyl side chain) and they have been prepared from commercially available material using simple reactions.
Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli 'Federico II', Via D. Montesano, 49, I-80131 Napoli, Italy.
Caterina
C
Fattorusso
Marco
M
Persico
Nicoletta
N
Basilico
Donatella
D
Taramelli
Ernesto
E
Fattorusso
Fernando
F
Scala
Orazio
O
Taglialatela-Scafati
D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004146:Dioxanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013329:Structure-Activity Relationship
D000962:Antimalarials; D004146:Dioxanes