Diez-Iriepa Daniel, Iriepa Isabel, López-Muñoz Francisco, Marco-Contelles José, Hadjipavlou-Litina Dimitra
Laboratory of Medicinal Chemistry, Institute of Organic Chemistry (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Ctra. Madrid-Barcelona km 33.6, Alcalá de Henares, 28871 Madrid, Spain.
Antioxidants (Basel). 2022 Aug 15;11(8):1575. doi: 10.3390/antiox11081575.
We report herein the synthesis and antioxidant profile of nine novel heterobisnitrones (hBNs) as new -phenyl--butylnitrone (PBN) analogues. The synthesized hBNs 1-9 were evaluated for their antioxidant activity using different in vitro techniques, while they were also tested as inhibitors of soybean LOX, as an indication of their anti-inflammatory effect. Nitrone hBN9 is the most potent antioxidant presenting higher anti-lipid peroxidation and hydroxyl radicals scavenging activities as well as higher lipoxygenase inhibition. In silico calculations reveal that hBN9 follows Lipinski's rule of five and that the molecule is able to penetrate theoretically the brain. All these results led us to propose hBN9 as a new potent antioxidant nitrone.
我们在此报告九种新型杂双硝酮（hBNs）作为新型 -苯基--丁基硝酮（PBN）类似物的合成及其抗氧化特性。使用不同的体外技术评估了合成的hBNs 1-9的抗氧化活性，同时还测试了它们作为大豆脂氧合酶（LOX）抑制剂的活性，以此作为其抗炎作用的指标。硝酮hBN9是最有效的抗氧化剂，具有更高的抗脂质过氧化和清除羟自由基的活性以及更高的脂氧合酶抑制作用。计算机模拟计算表明，hBN9符合Lipinski的五规则，并且该分子理论上能够穿透血脑屏障。所有这些结果促使我们提出hBN9作为一种新型有效的抗氧化硝酮。
