Development of rapid C-methylation between two sp3-hybridized carbons for incorporation of short-lived positron-emitting 11C radionuclide

2015 Fiscal Year Final Research Report

• Project/Area Number: 25460147
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Drug development chemistry
• Research Institution: Gifu University
• Principal Investigator: Koyama Hiroko 岐阜大学, 医学(系)研究科(研究院), 助教 (50402160)
• Co-Investigator(Kenkyū-buntansha): IJUIN Ryosuke 東京薬科大学, 薬学部, 助教 (40442925)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: PETプローブ合成 / アルキル－アルキル間クロスカップリング反応 / 高速反応 / ボロン化合物 / パラジウム触媒

Outline of Final Research Achievements

“Rapid C-[11C]methylation” is a groundbreaking methodology introduced for the synthesis of short-lived 11C-incorporated PET probes based on the use of C-C bond formation. The rapid cross-coupling reaction between two sp3-hybridized carbons remained to be explored. We developed Pd0-mediated cross couplings using CH3I (and [11C]CH3I) on the benzylic and allylic sp3 carbons applicable in various drug molecular structures. The utility of a rapid reaction was demonstrated by reacting between [11C]CH3I and boronic acid ester to afford N-(4-[11C]ethylphenyl)propionamide efficiently. The novel methodology possesses a high potential to incorporate the 11C radionuclide into organic frameworks in high reproducibility and high quality for human PET imaging.

Free Research Field

医歯薬学