One-Pot Evolution of Ageladine A through a Bio-Inspired Cascade towards Selective Modulators of Neuronal Differentiation

Takayuki Iwata, Satoshi Otsuka, Kazuki Tsubokura, Almira Kurbangalieva, Daisuke Arai, Koichi Fukase, Yoichi Nakao, Katsunori Tanaka

研究成果: Article査読

7 被引用数 (Scopus)

抄録

A bio-inspired cascade reaction has been developed for the construction of the marine natural product ageladine A and a de novo array of its N1-substituted derivatives. This cascade features a 2-aminoimidazole formation that is modeled after an arginine post-translational modification and an aza-electrocyclization. It can be effectively carried out in a one-pot procedure from simple anilines or guanidines, leading to structural analogues of ageladine A that had been otherwise synthetically inaccessible. We found that some compounds out of this structurally novel library show a significant activity in modulating the neural differentiation. Namely, these compounds selectively activate or inhibit the differentiation of neural stem cells to neurons, while being negligible in the differentiation to astrocytes. This study represents a successful case in which the native biofunction of a natural product could be altered by structural modifications.

本文言語English
ページ(範囲)14707-14716
ページ数10
ジャーナルChemistry - A European Journal
22
41
DOI
出版ステータスPublished - 2016 10 4

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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