醌类及结构相关的环氧乙烷衍生物的合成与抗疟活性
Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives.
作者信息
Carneiro Paula F, Pinto Maria C R F, Marra Roberta K F, da Silva Fernando de C, Resende Jackson A L C, Rocha E Silva Luiz F, Alves Hilkem G, Barbosa Gleyce S, de Vasconcellos Marne C, Lima Emerson S, Pohlit Adrian M, Ferreira Vitor F
机构信息
Universidade Federal do Rio de Janeiro, Instituto de Pesquisas de Produtos Naturais, 21944-970 Rio de Janeiro, RJ, Brazil.
Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, 24020-150 Niterói, RJ, Brazil.
出版信息
Eur J Med Chem. 2016 Jan 27;108:134-140. doi: 10.1016/j.ejmech.2015.11.020. Epub 2015 Nov 27.
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.
合成了一系列18种醌类化合物及其结构相关的环氧乙烷，并对其针对人类疟原虫恶性疟原虫氯喹敏感3D7克隆株的体外抑制活性进行了评估。2-氨基萘醌和2-烯丙氧基萘醌表现出重要的抗疟活性（半数抑制浓度（IC50）<10μM）。分别通过α-拉帕醌和四氯对苯醌与重氮甲烷在乙醚和乙醇的混合物中反应制备的环氧乙烷6和25，表现出最高的抗疟活性以及对人成纤维细胞（MCR-5细胞系）的低细胞毒性。这些活性化合物可能是抗疟先导分子的良好原型。
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