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, Hiroshi Nagase

Research output: Contribution to journalArticle

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 K opioid receptor activities even though many 5-arylmorphan compounds reported previously have shown selective ji opioid receptor activities. In addition, other related 5-arylmorphan derivatives showed potent dual antagonistic activities toward orexin 1 and 2 receptors.

Original languageEnglish (US)
Pages (from-to)134-144
Number of pages11
JournalHeterocycles
DOIs
StatePublished - Jan 1 2019
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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  • Cite this

    Yata, M., Kutsumura, N., Nagumo, Y., Yamamoto, N., Saitoh, T., Ishikawa, Y., Irukayama-Tomobe, Y., Yanagisawa, M., & Nagase, H. (2019). A novel rearrangement reaction of morphinan to arylmorphan skeletons and the pharmacologies of arylmorphan derivatives. Heterocycles, 134-144. https://doi.org/10.3987/COM-18-S(F)53