Synthesis and Characterization of New 7-Substituted 6,14-Ethenomorphinane Derivatives: N-{5-[(5α,7α)-4,5-Epoxy-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]-1,3,4-oxadiazol-2-yl}arenamines

✍ Scribed by Serkan Yavuz; Yılmaz Yıldırır

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 236 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000083

✦ Synopsis

In this study, (5a,7a)-4,5-epoxy-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-carboxylic acid hydrazide (5) was synthesized by the condensation of methyl (5a,7a)-4,5-epoxy-3,6-dimethoxy-17methyl-6,14-ethenomorphinan-7-carboxylate (4) with NH 2 NH 2 • H 2 O. The (5a,7a)-4,5-epoxy-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-carboxylic acid 2-[(arylamino)carbonyl]hydrazides 6a -6q were prepared by the reaction of 5 with corresponding substituted aryl isocyanates, and the N-{5-[(5a,7a)-4,5-epoxy-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]-1,3,4-oxadiazol-2-yl}arenamines 7a -7q were obtained via the cyclization reaction of 6a -6q in the presence of POCl 3 . The synthesized compounds have a rigid morphine structure, including the 6,14-endo-etheno bridge and the 5-(arylamino)-1,3,4-oxadiazol-2-yl residue at C(7) adopting the (S)-configuration (7a). The structures of the compounds were confirmed by high-resolution mass spectrometry (HR-MS) and various spectroscopic methods such as FT-IR, 1 H-NMR, 13 C-NMR, APT, and 2D-NMR (HETCOR, COSY, INADEQUATE).