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2022 Fiscal Year Final Research Report

Development and application of a convergent synthetic method for maleimide natural products

Research Project

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Project/Area Number 20K15960
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionTohoku Medical and Pharmaceutical University

Principal Investigator

Narita Koichi  東北医科薬科大学, 薬学部, 講師 (20584460)

Project Period (FY) 2020-04-01 – 2023-03-31
Keywordsオキサレイミド I / マレイミド / ヨウ化サマリウム / 天然物合成
Outline of Final Research Achievements

The maleimide segment of Oxaleimide I, a natural product with anticancer activity, was synthesized. It was discovered that the coupling reaction of the maleimide segment with aldehyde, followed by the elimination of the phenylthio group, proceeds continuously by employing samarium iodide. As a result, a successful convergent method for the synthesis of maleimide compounds was developed. Furthermore, the protecting group of the maleimide nitrogen was also investigated. A deprotectable protecting group was identified for acylmaleimide compounds, which are known for their high reactivity with nucleophiles and present challenges in deprotection.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

天然有機化合物は新たな創薬シードとして重要であるが、天然資源に依存するだけでは新たな医薬品を開発することは困難である。そこで、量的供給や誘導体化を可能とする天然物の全合成研究が創薬研究に果たす役割は大きい。本研究では抗がん活性を有するマレイミド天然物オキサレイミド I に着目して全合成研究を行った。本研究からマレイミドをアルデヒドと収束的に連結する独自の合成戦略を確立できた。アシルマレイミドを特徴とした化合物の合成が容易となり、医薬品シードとしての有用性が明らかになることで創薬研究の活性化に貢献できる。

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Published: 2024-01-30  

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