Synthetic study of biologically active alkaloids using bio-inspired reactions

2016 Fiscal Year Final Research Report

• Project/Area Number: 25288050
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Kumamoto University
• Principal Investigator: ISHIKAWA HAYATO 熊本大学, 大学院先端科学研究部, 准教授 (80453827)
• Co-Investigator(Kenkyū-buntansha): 高山 廣光 千葉大学, 薬学研究科(研究院), 教授 (90171561)
• Project Period (FY): 2013-04-01 – 2017-03-31
• Keywords: バイオインスパイアード反応 / 水中反応 / アルカロイド / 全合成 / ワンポット反応 / ジケトピペラジン

Outline of Final Research Achievements

A concise two one-pot synthesis of tryptophan-based dimeric diketopiperazine alkaloid is detailed based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and one-pot procedure for construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10% up to 27%. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin-specific protease 7 (USP7) and foam cell formation in macrophages. The newly listed biological evaluation for tryptophan-based dimeric diketopiperazine alkaloids discovered 15,15-bis-epi-eurocristatine , 1-(2-phenylethylene)-ditryptophenaline, and WIN 64745 as new drug candidates.

Free Research Field

有機合成化学