Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues

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• 作者：I. Wauters ; H. Goossens ; E. Delbeke ; K. Muylaert ; B. I. Roman ; K. Van Hecke ; V. Van Speybroeck ; C. V. Stevens
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：August 21, 2015
• 年：2015
• 卷：80
• 期：16
• 页码：8046-8054
• 全文大小：506K
• ISSN：1520-6904

文摘

A method for the preparation of 3,5-bridged piperazin-2-ones from a tryptophan鈥損roline-based diketopiperazine is described using diphosgene to induce the ring closure. Density functional theory calculations were conducted to study the mechanism of this C鈥揅 bond formation. Several derivatives of the thus obtained 伪-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.