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Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives
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Abstract:
A series of eighteen quinones and structurally-related oxiranes were synthesized and evaluated for in vitro inhibitory activity against the chloroquine-sensitive 3D7 clone of the human malaria parasite Plasmodium falciparum. 2-amino and 2-allyloxynaphthoquinones exhibited important antiplasmodial activity (median inhibitory concentrations (IC50) < 10 μM). Oxiranes 6 and 25, prepared respectively by reaction of α-lapachone and tetrachloro-p-quinone with diazomethane in a mixture of ether and ethanol, exhibited the highest antiplasmodial activity and low cytotoxicity against human fibroblasts (MCR-5 cell line). The active compounds could represent a good prototype for an antimalarial lead molecule. © 2015 Published by Elsevier Masson SAS.
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2 (allyloxy) 4h Spiro(naphthalene 1,2' Oxirane) 4 One, 2 (phenylamino) 4h Spiro(naphthalene 1,2' Oxirane) 4 One, 2 Amino 4h Spiro(naphthalene 1,2' Oxirane) 4 One, 2,2 Dimethyl 2,3 Dihydro 4h Spiro[naphtho[2,3 B]furan 9,2' Oxiran] 4 One, 2,3 Dichloro 4h Spiro(naphthalene 1,2' Oxirane) 4 One, 4,5 Dichloro 3,6 Dimethoxyphthalonitrile, 4,5,7,8 Tetrachloro 1 Oxaspiro[2.5]octa 4,7 Dien 6 One, Antimalarial Agent, Chloroquine, Ethylene Oxide, Ethylene Oxide Derivative, Methyl 9 Phenanthryl Ether, Naphthoquinone, Quinone Derivative, Unclassified Drug, Antimalarial Agent, Ethylene Oxide, Quinone Derivative, Antimalarial Activity, Controlled Study, Drug Screening, Drug Structure, Drug Synthesis, Ic 50, In Vitro Study, Inhibitory Concentration, Nonhuman, Plasmodium, Plasmodium Falciparum, X-ray Diffraction, Cell Line, Cell Survival, Chemical Structure, Chemistry, Dose Response, Drug Effects, Drug Sensitivity, Fibroblast, Human, Structure Activity Relation, Synthesis, Antimalarials, Cell Line, Cell Survival, Dose-response Relationship, Drug, Ethylene Oxide, Fibroblasts, Humans, Molecular Structure, Parasitic Sensitivity Tests, Plasmodium Falciparum, Quinones, Structure-activity Relationship