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 v...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1989/05/25, Vol.37(5), pp.1245-1248
Hauptverfasser:	HORI, Mikio, IWAMURA, Tatsunori, IMAI, Eiji, SHIMIZU, Hiroshi, KATAOKA, Tadashi, NOZAKI, Masakatsu, NIWA, Masayuki, FUJIMURA, Hajime
Format:	Artikel
Sprache:	eng
Schlagworte:	3-carbamoylthio-3-deoxydihydromorphine analgesic Analgesics - chemical synthesis Animals antinociceptive activity Chemical Phenomena Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives In Vitro Techniques Morphinans - chemical synthesis Morphinans - pharmacology Newman-Kwart rearrangement opioid receptor Organic chemistry Preparations and properties Rats sulfur-containing morphinan
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Zusammenfassung:	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-Carbamoylthiodeoxydihydromorphine had no significant analgetic activity.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.37.1245