Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, CNRS, 57 rue Cuvier, 75005, Paris, France.
Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.
Chemistry. 2018 Nov 7;24(62):16686-16691. doi: 10.1002/chem.201804023. Epub 2018 Oct 21.
An intramolecular Diels-Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels-Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines while actin polymerization is preserved.
报道了一种 Schreiner 硫脲高效促进的分子内 Diels-Alder（IMDA）反应，用于构建具有生物功能的细胞松弛素骨架（periconiasin 系列）。DFT 计算突出了这种催化作用中的独特的多齿协同氢键。保护基的去除策略得到了一系列不同结构的产物，并展示了 Diels-Alder 环加成产物在功能化后的特殊反应性。生物研究表明，一些化合物对乳腺癌细胞系具有很强的细胞毒性，而肌动蛋白聚合则得以保留。
