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Synthesis and Pharmacological Evaluation of Some Novel Thebaine Derivatives: N ‐(Tetrazol‐1 H ‐5‐yl)‐6,14‐endoethenotetrahydrothebaine Incorporating the 1,3,4‐Oxadiazole or the 1,3,4‐Thiadiazole Moiety
Author(s) -
Yavuz Serkan,
Ünal Yusuf,
Pamir Özgür,
Yılmazer Demet,
Kurtipek Ömer,
Kavutçu Mustafa,
Arslan Mustafa,
Ark Mustafa,
Yıldırır Yılmaz
Publication year - 2013
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201200451
Subject(s) - thebaine , oxadiazole , chemistry , pharmacology , combinatorial chemistry , stereochemistry , organic chemistry , medicine , morphine , codeine
In this study, we synthesized some novel N ‐(tetrazol‐1 H ‐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 of their IR, 1 H NMR, 13 C NMR, 2D NMR, and high‐resolution mass spectral data. The analgesic activity was evaluated by a rat‐hot plate test model and a rat tail‐flick model. Compound 12 showed analgesic activity higher than that of morphine. In addition to a histopathological and biochemical evaluation, the LD 50 dose for the most active compound 12 was determined.