100448-10-0Relevant academic research and scientific papers
Probes for narcotic receptor mediated phenomena. Part 42: Synthesis and in vitro pharmacological characterization of the N-methyl and N-phenethyl analogues of the racemic ortho-c and para-c oxide-bridged phenylmorphans
Kim, Jin-Hee,Deschamps, Jeffrey R.,Rothman, Richard B.,Dersch, Christina M.,Folk, John E.,Cheng, Kejun,Jacobson, Arthur E.,Rice, Kenner C.
scheme or table, p. 3434 - 3443 (2011/07/08)
A new synthesis of N-methyl and N-phenethyl substituted ortho-c and para-c oxide-bridged phenylmorphans, using N-benzyl- rather than N-methyl-substituted intermediates, was used and the pharmacological properties of these compounds were determined. The N-
Probes for narcotic receptor mediated phenomena. 37.1 Synthesis and opioid binding affinity of the final pair of oxide-bridged phenylmorphans, the ortho- and para-b-isomers and their N-phenethyl analogues, and the synthesis of the N-phenethyl analogues of the ortho- and para-d-isomers
Kurimura, Muneaki,Liu, Hehua,Sulima, Agnieszka,Hashimoto, Akihiro,Przybyl, Anna K.,Ohshima, Etsuo,Kodato, Shinichi,Deschamps, Jeffrey R.,Dersch, Christina M.,Rothman, Richard B.,Yong, Sok Lee,Jacobson, Arthur E.,Rice, Kenner C.
experimental part, p. 7866 - 7881 (2009/12/07)
In the isomeric series of 12 racemic topologically rigid N-methyl analogues of oxide-bridged phenylmorphans, all but two of the racemates, the ortho- and para-b-oxide-bridged phenylmorphans 20 and 12, have remained to be synthesized. The b-isomers were very difficult to synthesize because of the highly strained 5,6-transfused ring junction that had to be formed. Our successful strategy required functionalization of the position para (or ortho) to a fluorine atom on the aromatic ring using an electron-withdrawing nitro group to activate that fluorine. The racemic N-phenethyl analogues 24 and 16 were moderately potent κ-receptor antagonists in the [35S]GTPγS assay. We synthesized the N-phenethyl-substituted oxide-bridged phenylmorphans in the ortho- and para-d-oxide-bridged phenylmorphan series (51 and 52) which had not been previously evaluated using contemporary receptor binding assays to see whether they also have higher affinity for opioid receptors than their N-methyl relatives 46 and 47.
Probes for Narcotic Receptor Mediated Phenomena. 9. Synthesis of (+/-)-(3α,6aα,11aβ)-1,3,4,5,6,11a-Hexahydro-2-methyl-2H-3,6a-methanobenzofuroazocin-10-ol, an Oxide-Bridged 5-(m-Hydroxyphenyl)morphan
Burke, Terrence R.,Jacobson, Arthur E.,Rice, Kenner C.,Weissman, Ben Avi,Huang, Hsueh-Cheng,Silverton, J. V.
, p. 748 - 751 (2007/10/02)
The synthesis of racemic (3α,6aα,11aβ)-1,3,4,5,6,11a-hexahydro-2-methyl-2H-3,6a-methanobenzofuroazocin-10-ol (2d) is described.The route used acid-catalyzed ring closure of enamine 5 to yield the unsaturated phenylmorphan 6.Conversion of 6 to oxide
