Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues

作者:Wauters I; Goossens H; Delbeke E; Muylaert K; Roman B I; Van Hecke K; Van Speybroeck V; Stevens C V*
来源:Journal of Organic Chemistry, 2015, 80(16): 8046-8054.
DOI:10.1021/acs.joc.5b01161

摘要

A method for the preparation of 3,5-bridged piperazin-2-ones from a tryptophan proline-based diketopiperazine is described using diphosgene to induce the ring closure. Density functional theory calculations were conducted to study the mechanism of this C-C bond formation. Several derivatives of the thus obtained alpha-chloroamine were synthesized by substitution of the chlorine atom using a range of O-, N-, S-, and C-nucleophiles. This novel class of brevianamide F analogues possess interesting breast cancer resistance protein inhibitory activity.

  • 出版日期2015-8-21