91110-26-8Relevant academic research and scientific papers
Synthesis and characterization of new thebaine derivatives as potential opioid agonists and antagonists: 2-[ N -(1 H -Tetrazol-5-yl)-6,14-endo-etheno-6, 7,8,14-tetrahydrothebaine-7α-yl]-5-phenyl-1,3,4-oxadiazoles
Yildirir, Yilmaz,Pamir, Oezguer,Yavuz, Serkan,Disli, Ali
, p. E93-E99 (2013)
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.
Synthesis and pharmacological evaluation of some novel thebaine derivatives: N-(tetrazol-1H-5-yl)-6,14-endoethenotetrahydrothebaine incorporating the 1,3,4-oxadiazole or the 1,3,4-thiadiazole moiety
Yavuz, Serkan,Uenal, Yusuf,Pamir, Oezguer,Yilmazer, Demet,Kurtipek, Oemer,Kavutcu, Mustafa,Arslan, Mustafa,Ark, Mustafa,Yildirir, Yilmaz
, p. 455 - 462 (2013/07/26)
In this study, we synthesized some novel N-(tetrazol-1H-5-yl)-6,14- endoethenotetrahydrothebaine 7α-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives as potential analgesic agents. The structures of the compounds were established on the basis
Preparation of 7-(1,3,4-Oxadiazolyl)-6,14-endo-etheno-6,7,8,14-tetrahydrothebaines and Related Compounds as Potential Analgesics
Bentley, Kenneth W.,Burton, Michael,Uff, Barrie C.
, p. 1276 - 1280 (2007/10/02)
General procedures for the preparation of 7α-(2-substituted-1,3,4-oxadiazol-5-yl)-6,14-endo-etheno-6,7,8,14-tetrahydrothebaines are described.Substituents include alkyl, aryl, amino, cycloamino, and alkylthio functions.Many of these and related compounds
