Malaria is an important disease causing many death in several countries of Africa and Asia. In these continents, some plants such as Garcinia cola are used to fight against this disease because they contain xanthone derivatives which present antiplasmodial activity. The present theoretical study aims to establish a relationship between the electronic structure and the antiplasmodial activity of some xanthone derivatives, and more specifically to build a 2D-pharmacophore model in order to predict the biological activity of xanthone derivatives. The calculations are performed within the density functional theory (DFT) using the B3LYP/6-31G(d,p) level of theory. The developed approach quantitative structure-activity relationship (QSAR) follows the Klopman-Peradejordi-Gómez (KPG) methodology. We obtain a statistically significant equation relating the variation of the logarithm of half maximal inhibitory concentration (log(IC50)) with the variation of the numerical values of a set of eight local atomic reactivity descriptors (R = 0.98, R2 = 0.97, adj-R2 = 0.95, F(8.13) = 48.63, p < 0.00000, SD 0.08). The antiplasmodial activity seems to be driven by atomic orbitals and charges. Our 2D-pharmacophore model should be useful to propose new xanthone derivatives with higher antiplasmodial activity.

中文翻译：

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氧杂蒽酮衍生物的电子结构与抗疟原虫活性的关系：二维-QSAR 方法

疟疾是一种在非洲和亚洲的一些国家造成许多人死亡的重要疾病。在这些大陆，一些植物如藤黄可乐被用来对抗这种疾病，因为它们含有具有抗疟原虫活性的呫吨酮衍生物。本理论研究旨在建立一些氧杂蒽酮衍生物的电子结构与抗疟原虫活性之间的关系，更具体地说，建立二维药效团模型以预测氧杂蒽酮衍生物的生物活性。计算是在密度泛函理论 (DFT) 内使用 B3LYP/6-31G(d,p) 理论水平进行的。开发的方法定量构效关系 (QSAR) 遵循 Klopman-Peradejordi-Gómez (KPG) 方法。我们获得了一个统计学上显着的方程，该方程将半数最大抑制浓度 (log(IC50)) 的对数变化与一组八个局部原子反应性描述符 (R = 0.98, R2 = 0.97, adj- R2 = 0.95，F(8.13) = 48.63，p < 0.00000，SD 0.08)。抗疟原虫活性似乎是由原子轨道和电荷驱动的。我们的 2D 药效团模型应该有助于提出具有更高抗疟原虫活性的新氧杂蒽酮衍生物。