title: Facile synthesis of 8-benzoylthio-2,6-methano-3-benzazocines and 3-benzoylthiomorphinans having small-ring substituents.
abstract: Synthesis of 3-cyclopropylmethyl-, 3-cyclobutylmethyl-, and 3-methyl-8-benzoylthio-2,6-methano-3-benzazocines (1j-l) was performed by regio-selective chlorosulfonation of non-narcotic 8-deoxy derivatives (1a-c) followed by reduction and benzoylation. 3-Benzoylthiomorphinans (2h-j) were also obtained by the same method. Compounds having small-ring substituents (1k, 1l, 2i, 2j) were found to be weak but pure mu- and delta-opioid antagonists. The analgetic activity of 1k was almost equal to that of pentazocine.
authors.forename: M
authors.initials: M
authors.lastname: Hori
authors.forename: T
authors.initials: T
authors.lastname: Iwamura
authors.forename: T
authors.initials: T
authors.lastname: Morita
authors.forename: E
authors.initials: E
authors.lastname: Imai
authors.forename: H
authors.initials: H
authors.lastname: Oji
authors.forename: T
authors.initials: T
authors.lastname: Kataoka
authors.forename: H
authors.initials: H
authors.lastname: Shimizu
authors.forename: M
authors.initials: M
authors.lastname: Ban
authors.forename: M
authors.initials: M
authors.lastname: Nozaki
authors.forename: M
authors.initials: M
authors.lastname: Niwa
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D001575:Benzomorphans / Q000138:chemical synthesis* / Q000494:pharmacology; D001667:Binding, Competitive / Q000187:drug effects; D008297:Male; D051379:Mice; D009019:Morphinans / Q000138:chemical synthesis* / Q000494:pharmacology; D010423:Pentazocine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D011957:Receptors, Opioid / Q000187:drug effects / Q000378:metabolism
chemical_list: D000700:Analgesics; D001575:Benzomorphans; D009019:Morphinans; D011957:Receptors, Opioid; D010423:Pentazocine