Bicyclic Piperazine Mimetics of the Peptide β-Turn Assembled via the Castagnoli-Cushman Reaction

Liliia Usmanova, Dmitry Dar'In, Mikhail S. Novikov, Maxim Gureev, Mikhail Krasavin

Research output

4 Citations (Scopus)

Abstract

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli-Cushman reaction of protected iminodiacetic anhydride) were converted into cis- and trans-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-Fsp3 cores for drug design in general. The methodology was applied to the preparation of ring-expanded version of bicyclic piperazines not described in the literature.

Original languageEnglish
Pages (from-to)5859-5868
Number of pages10
JournalJournal of Organic Chemistry
Volume83
Issue number10
DOIs
Publication statusPublished - 18 May 2018

Scopus subject areas

  • Organic Chemistry

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