Neukirch Hannes, Kaneider Nicole C, Wiedermann Christian J, Guerriero Antonio, D'Ambrosio Michele
Laboratorio di Chimica Bioorganica, Università degli Studi di Trento, Via Sommarive 14, 38050 Povo (Trento), Italy.
Bioorg Med Chem. 2003 Apr 3;11(7):1503-10. doi: 10.1016/s0968-0896(02)00553-9.
The present study has achieved the photochemical conversion of a germacrolide into a melampolide. The investigation on their chemical properties allowed us to evaluate the minimum interatomic distance needed for transannular bridging of C(10) ring in germacrolides and to explain the regiochemical selectivity of electrophilic cyclizations. The antiinflammatory activity of parthenolide and its semisynthetic derivatives was evaluated by in vitro chemotaxis assay with human neutrophiles. These structure-activity relationship studies have led to hypothesize a new pharmacophore and have provided useful information for computationally designed drugs.
本研究实现了吉马内酯向美兰坡内酯的光化学转化。对它们化学性质的研究使我们能够评估吉马内酯中C(10)环跨环桥接所需的最小原子间距离，并解释亲电环化反应的区域化学选择性。通过用人中性粒细胞进行体外趋化试验，评估了小白菊内酯及其半合成衍生物的抗炎活性。这些构效关系研究促使人们提出了一种新的药效团，并为计算机辅助设计药物提供了有用信息。
