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Paper | Regular issue | Vol 98, No. 10, 2019, pp.1423-1435
Published online, 28th October, 2019
DOI: 10.3987/COM-19-14161
Elucidation of The Conformational Properties of 3-Pyridinoyl Indoles as Intermediates of Cannabimimetics

Hideyo Takahashi,* Koji Araki, Hidetsugu Tabata, Kosho Makino, Ryohei Ujiie, Kohei Sezaki, Hiroshi Nakayama, Tetsuta Oshitari, and Hideaki Natsugari

*Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan

Abstract

The conformations of 3-pyridinoyl indoles, which are intermediates of 5-fluoropentyl-3-pyridinoyl indole, were investigated using their X-ray crystal structures. All derivatives existed as s-trans conformers. A pseudo-planar conformation was observed in the 2'-yl isomer of 3-pyridinoyl indoles. On the other hand, twisted conformations were observed in 3-pyridinoyl 2-methylindoles. The conformations of these compounds in solution were also investigated using VT-NMR.