2-芳基-3H-吲哚-3-酮：合成、电化学行为和抗疟活性。
2-Aryl-3H-indol-3-ones: synthesis, electrochemical behaviour and antiplasmodial activities.
机构信息
Université de Toulouse III, UPS, PHARMA-DEV, UMR 152, 118 Route de Narbonne, F-31062 Toulouse Cedex 9, France; IRD, UMR 152, F-31062 Toulouse Cedex 9, France.
Université de Toulouse III, UPS, PHARMA-DEV, UMR 152, 118 Route de Narbonne, F-31062 Toulouse Cedex 9, France; IRD, UMR 152, F-31062 Toulouse Cedex 9, France.
出版信息
Eur J Med Chem. 2014 May 6;78:269-74. doi: 10.1016/j.ejmech.2014.03.059. Epub 2014 Mar 18.
The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2-(4-dimethylaminophenyl)-5-methoxy-indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond.
本文描述了吲哚啉衍生物的合成及其在体外对红内期疟原虫的抗疟活性。通过氧化吲哚啉-N-氧化物的脱氧反应合成了 2-芳基-3H-吲哚-3-酮。比较了它们的电化学行为、抗疟活性和对人肿瘤细胞系的细胞毒性。这些化合物的抗疟 IC50（50%抑制浓度）范围在 49 和 1327 nM 之间。其中，2-(4-二甲基氨基苯基)-5-甲氧基-吲哚-3-酮（7）在体外具有最好的抗疟活性（IC50=49 nM；FcB1 株）和选择性指数（SI（CC50 MCF7/IC50 FcB1）=423.4）。因此，在脱氧系列中发现的这些活性化合物与 N-氧化物系列中的结构类似物具有相当的电化学行为，在氮-碳双键处。
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