新型荧光团硼异喹啉的合成及其荧光性质

Sóvári Dénes, Kormos Attila, Demeter Orsolya, Dancsó András, Keserű György Miklós, Milen Mátyás, Ábrányi-Balogh Péter

Hungarian Academy of Sciences, Research Centre for Natural Sciences, Institute of Organic Chemistry, Medicinal Chemistry Research Group 1519 Budapest POB 286 Hungary

Hungarian Academy of Sciences, Research Centre for Natural Sciences, Institute of Organic Chemistry, Chemical Biology Research Group 1519 Budapest POB 286 Hungary.

RSC Adv. 2018 Nov 15;8(67):38598-38605. doi: 10.1039/c8ra08241c. eCollection 2018 Nov 14.

First representatives of a new family of isoquinolines, so called boroisoquinolines, were synthesized and characterized. The synthesis was based on the insertion of the difluoroboranyl group into the 1-methylidene-3,4-dihydroisoquinoline core. The optimization of the 2-difluoroboranyl-3,4-dihydroisoquinoline-1(2)-ylidene core led to efficient fluorescence in a range of 400-600 nm with outstanding (>100 nm) Stokes shifts. The compounds might be suitable for reversible or irreversible labelling of proteins, particularly the cannabinoid receptor CB.

首个新的异喹啉家族（即所谓的硼代异喹啉）的代表物得以合成与表征。该合成基于将二氟硼烷基团插入1-亚甲基-3,4-二氢异喹啉核心结构中。对2-二氟硼烷基-3,4-二氢异喹啉-1(2)-亚基核心结构的优化，使其在400 - 600 nm范围内产生高效荧光，并具有出色的（>100 nm）斯托克斯位移。这些化合物可能适用于蛋白质的可逆或不可逆标记，尤其是大麻素受体CB。