Naphtho and benzo analogs of the .kappa. opioid agonist trans-(.+-.)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide

Abstract

Further elaboration on the structure-activity relationships in our U-50,488 series has revealed that benzologation of this cyclohexane-1,2-diamine derivative provides compounds which either maintain the interaction with the kappa receptor (e.g. compounds 3a and 5a in the phenylacetamido series) or eliminate the mu receptor mediated analgesia (e.g. compounds 3-6 in the benzamido series). Naphthologation also caused the elimination of mu receptor mediated analgesia (e.g. compounds 17a and 17b).

Near death from a novel synthetic opioid labeled U-47700: emergence of a new opioid class

“…The toxicity he manifested (depressed level of consciousness and respiratory depression) and its reversal with naloxone administration is consistent with the known in vitro and in vivo opioid agonism of U-47700. [14,15] We are not aware of any metabolic or pharmacokinetic data on U-47700, nor any literature detailing any therapeutic effects of U-47700 in humans. Two recently published cases detail the identification of U-47700 postmortem and implicate its use in the deaths.…”

Anthracene-Induced Turnover Enhancement in the Manganese Porphyrin-Catalyzed Epoxidation of Olefins

“…The products were analyzed by GC-MS and 1 H NMR spectroscopy. Data for the following compared favorably with reported spectral characterization: 4-methoxystyrene oxide, 25 4methylstyrene oxide, 26 4-tert-butylstyrene oxide, 25 4-chlorostyrene oxide, 26 4-trifluoromethylstyrene oxide, 27 4-nitrostyrene oxide, 26 1,4dihydronaphthalene oxide, 28 and 1,2-dihydronaphthalene oxide. 24 General Procedures for Epoxidation Reactions.…”

Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Phenols

“…Ring-opening carbon–oxygen bond formation with oxabenzonorbornadiene 1 is a valuable synthetic methodology to create highly functionalized ring systems. These methods offer potentially useful routes to the synthesis of enantioenriched trans -2-phenoxy-1,2-dihydronaphthalen-1-ols, which are the scaffolds for total synthesis of bioactive compounds . Herein we report the full details of the catalytic ARO reaction of oxabenzonorbornadienes with phenols in the presence of iridium catalysts.…”