Department of Chemistry and Biochemistry, University of Wisconsin Milwaukee, Milwaukee, WI 53211, USA.
RTI International, Center for Drug Discovery, Research Triangle Park, Durham, NC 27709, USA.
Molecules. 2021 Jun 7;26(11):3459. doi: 10.3390/molecules26113459.
Bisindoles are structurally complex dimers and are intriguing targets for partial and total synthesis. They exhibit stronger biological activity than their corresponding monomeric units. Alkaloids, including those containing C-19 methyl-substitution in their monomeric units, their synthetic derivatives, and their mismatched pairs can be attractive targets for synthesis and may unlock better drug targets. We herein discuss the isolation of bisindoles from various species, their bioactivity, putative biosynthesis, and synthesis. The total synthesis of macralstonidine, macralstonine, -acetylmacralstonine, and dispegatrine, as well as the partial synthesis of alstonisidine, villalstonine, and macrocarpamine are also discussed in this review. The completion of the total synthesis of pleiocarpamine by Sato et al. completes the formal synthesis of the latter two bisindoles.
双茚并吲哚类化合物结构复杂，是部分和全合成的有趣目标。它们的生物活性比相应的单体单元更强。生物碱，包括其单体单元中含有 C-19 甲基取代的生物碱、其合成衍生物及其不匹配对，可能是合成的有吸引力的目标，并可能解锁更好的药物靶点。本文讨论了从各种物种中分离出的双茚并吲哚类化合物，它们的生物活性、假定的生物合成和合成。本文还讨论了 macralstonidine、macralstonine、-acetylmacralstonine 和 dispegatrine 的全合成，以及 alstonisidine、villalstonine 和 macrocarpamine 的部分合成。Sato 等人完成了 pleiocarpamine 的全合成，从而完成了后两种双茚并吲哚类化合物的正式合成。
