| Popis: |
In this study, we report the synthesis a series of novel 2-[N-(1H-tetrazol-5-yl)-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine-7α-yl]-5-phenyl-1,3,4-oxadiazole derivatives (7a–e) which have potential opioid antagonist and agonist. The substitution reaction of 6,14-endo-ethenotetrahydrothebaine-7α-carbohydrazide with corresponding benzoyl chlorides gave diacylhydrazine compounds 4a–e in good yields. The treatment of compounds 4a–e with POCl3 caused the conversion of side-chain of compounds 5a–e into 1,3,4-oxadiazole ring at C(7) position; thus, compounds 5a–e were obtained. Subsequently, cyanamides (6a–e) were prepared from compounds 5a–e and then compounds 7a–e were synthesized by the azidation of 6a–e with NaN3. The structures of the compounds were established on the basis of their IR, 1H NMR, 13C APT, 2D-NMR (COSY, NOESY, HMQC, HMBC) and high-resolution mass spectral data. |
