School of Chemistry & Molecular Bioscience, Molecular Horizons , University of Wollongong, and Illawarra Health & Medical Research Institute , Wollongong , New South Wales 2522 , Australia.
School of Chemistry , The Australian National University , Canberra , Australian Capital Territory 2601 , Australia.
J Org Chem. 2019 Sep 6;84(17):11228-11239. doi: 10.1021/acs.joc.9b01442. Epub 2019 Aug 15.
The nucleophilic addition of organomagnesium and organolithium species to the cheap and robust natural dye indigo led to desymmetrization of the heterocyclic nucleus via a Grignard addition-dehydration procedure. Twenty-seven diversely functionalized [1,3']-3-substituted 2,2'-diindol-3'-ones were synthesized by this methodology, with several showing submicromolar inhibition and exquisite selectivity against parasites (3D7 and Dd2 strains) . This work demonstrates the utility of indigo dye as a highly versatile scaffold for the synthesis of structurally diverse, bioactive heterocycles.
通过格氏加成-脱水反应，将有机镁和有机锂物种的亲核加成到廉价且坚固的天然染料靛蓝上，导致杂环核的非对称化。通过这种方法合成了二十七个具有不同官能团的[1,3']-3-取代 2,2'-二吲哚-3'-酮，其中几个对寄生虫（3D7 和 Dd2 株）表现出亚微摩尔的抑制作用和极好的选择性。这项工作证明了靛蓝染料作为合成结构多样、生物活性杂环的高度通用支架的实用性。
