Unexpected Rearrangement Reactions of the 14-Aminonaltrexone Skeleton.
Org Lett
; 25(19): 3407-3411, 2023 05 19.
Article
in En
| MEDLINE
| ID: mdl-37154730
ABSTRACT
The reaction of 14-aminonaltrexone with acetic anhydride was found to produce a range of different novel compounds between the free compound and its hydrochloride. The hydrochloride produced a compound with an acetylacetone moiety, whereas the free form produced a compound with a pyranopyridine moiety. Efforts to isolate reaction intermediates and density functional theory calculations have elucidated those formation mechanisms with both bearing the novel morphinan-type skeleton. Furthermore, a derivative with the acetylacetone moiety showed binding to opioid receptors.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Pentanones
/
Morphinans
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2023
Document type:
Article
Affiliation country:
Japón