Synthesis and analgetic activity of sulfur-containing morphinans and related compounds.
3-Acylthiomorphinans, 3-carbamoylthio-3-deoxydihydromorphine and 3-benzoylthio-9-aza-17-carbamorphinan were synthesized by Newman-Kwart rearrangement of the corresponding O-thiocarbamates. The analgetic activities were lower than that of pentazocine, and the opioid receptor binding affinities were very weak. These acylthiomorphinans showed low antinociceptive activity compared with corresponding sulfur-containing benzomorphans. 3-Carbamoylthio-deoxydihydromorphine had no significant analgetic activity.
Hori
M
M
Iwamura
T
T
Imai
E
E
Shimizu
H
H
Kataoka
T
T
Nozaki
M
M
Niwa
M
M
Fujimura
H
H
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D066298:In Vitro Techniques; D009019:Morphinans / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats
D000700:Analgesics; D009019:Morphinans