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Communication | Special issue | Vol 99, No. 1, 2019, pp.134-144
Published online, 7th February, 2019
DOI: 10.3987/COM-18-S(F)53
A Novel Rearrangement Reaction of Morphinan to Arylmorphan Skeletons and the Pharmacologies of Arylmorphan Derivatives

Masahiro Yata, Noriki Kutsumura, Yasuyuki Nagumo, Naoshi Yamamoto, Tsuyoshi Saitoh, Yukiko Ishikawa, Yoko Irukayama-Tomobe, Masashi Yanagisawa, and Hiroshi Nagase*

*International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan

Abstract

A novel rearrangement reaction of the morphinan skeleton by using zinc iodide was developed. The substrate-specific rearrangement afforded two types of novel 5-arylmorphan derivatives, i.e., compounds produced by either a 1,5-shift of the nitrogen bridge or a 1,3-shift of the nitrogen bridge in a starting morphinan derivative. The 5-arylmorphan derivatives showed selective κ opioid receptor activities even though many 5-arylmorphan compounds reported previously have shown selective µ opioid receptor activities. In addition, other related 5-arylmorphan derivatives showed potent dual antagonistic activities toward orexin 1 and 2 receptors.