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 language | English (US) |
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Pages (from-to) | 134-144 |
Number of pages | 11 |
Journal | Heterocycles |
Volume | 99 |
Issue number | 1 |
DOIs | |
State | Published - 2019 |
Externally published | Yes |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry