Sterically Constrained and Encumbered: An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core

    Research output

    9 Citations (Scopus)

    Abstract

    The combination of two privileged motifs, that is, indoline and the constrained peptidomimetic piperazine-2,5-dione, within one tricyclic structure resulted in a scaffold that is abundant in nature but surprisingly scarce in the domain of synthetic bioactive molecules. Utilizing the power of the isocyanide-based Joullié–Ugi reaction followed by postcondensation cyclization, we synthesized such compounds with four elements of diversity in good yields from readily available precursors. The compounds are constrained peptidomimetics distinctly encumbered in a steric sense and have a pronounced three-dimensional character, which is a highly desirable feature in modern drug design.

    Original languageEnglish
    Pages (from-to)1740-1744
    Number of pages5
    JournalEuropean Journal of Organic Chemistry
    Volume2017
    Issue number13
    DOIs
    Publication statusPublished - 3 Apr 2017

    Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry

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