Nucleophilic deoxyfluorination of phenol derivatives and its application to drug discovery

2015 Fiscal Year Final Research Report

• Project/Area Number: 24390005
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Osaka University (2013-2015); University of Shizuoka (2012)
• Principal Investigator: AKAI Shuji 大阪大学, 薬学研究科(研究院), 教授 (60192457)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: フェノール / フッ素陰イオン / 含フッ素芳香族化合物 / ビアリール / 抗腫瘍活性物質 / ベンザイン / 創薬 / 有機合成化学

Outline of Final Research Achievements

In modern drug discovery, fluorine has served as one of the most important heteroatoms because the introduction of fluorine atom(s) into bioactive molecules often improves their properties such as biological activity, metabolic stability, bioavailability and lipophilicity. Therefore, the development of new synthetic methods for the regioselective introduction of fluorine atom(s) into bioactive molecules are highly desired to enhance the drug discovery.
In this project, two methods for nucleophilic deoxyfluorination of phenol and catechol derivatives have been developed. The deoxyfluorination along with the construction of bridged biaryl framework has also been devised. Validations of these methods are given in the synthesis of new fluorinated analogs of known anticancer allocolchicinoids as well as the convergent synthesis of the antipsychotic drug risperidone.

Free Research Field

有機合成化学