Development of a general synthetic method for selenium-containing derivatives using copper-catalyzed tandem reactions

2023 Fiscal Year Final Research Report

• Project/Area Number: 19K07005
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
• Research Institution: Aichi Gakuin University
• Principal Investigator: Shuji Yasuike 愛知学院大学, 薬学部, 教授 (10230210)
• Co-Investigator(Kenkyū-buntansha): 小幡 徹 愛知学院大学, 薬学部, 准教授 (20324080)
• Project Period (FY): 2019-04-01 – 2024-03-31
• Keywords: セレン含有誘導体 / タンデム反応 / 触媒反応 / 一般合成法

Outline of Final Research Achievements

In this research project, we aimed to develop a method for the introduction of any substituent including heterocycles to selenium atoms using tandem reactions based on C-H activation reactions under transition metal catalysts such as copper. As a result, the synthesis of unsymmetrical diaryl selenides with imidazole moieties using three-component reactions could not be achieved, but selenation of uracils and antipyrines using three-component reactions under copper and silver catalysts could be achieved. We have also established a method for the synthesis and spectroscopic characterization of benzimidazobenzoselenoazoles, a selenium-containing tetracyclic compound that does not require transition metal as an intramolecular tandem reaction. Furthermore, anti-tumor activity was observed in some of the obtained compounds.

Free Research Field

化学系薬学

Academic Significance and Societal Importance of the Research Achievements

セレンは，生体内で必須微量元素として機能している．また，創薬においても有機セレン化合物が着目されはじめている．しかしながら，従来まで複素環を持つ非対称ジアリールセレニドの合成では，Se源の調整が繁雑で簡単な一般合成法はこれまで確立されていなかった．本課題では，安価で取り扱い容易なSe末を主なSe源に利用した触媒的C－H活性化反応を基軸とした三成分反応を含むタンデム型セラニル化を新たに確立した．本法を活用することで有機セレン化合物の供給が容易となり，新しい生理活性物質の創製に活用されることが期待される．