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

被引：18
|
作者：
Yavuz, Serkan [1 ]
Unal, Yusuf [2 ]
Pamir, Ozgur [1 ]
Yilmazer, Demet [3 ]
Kurtipek, Omer [2 ]
Kavutcu, Mustafa [4 ]
Arslan, Mustafa [4 ]
Ark, Mustafa [5 ]
Yildirir, Yilmaz [1 ]
机构：
[1] Gazi Univ, Fac Sci, Dept Chem, TR-06500 Ankara, Turkey
[2] Gazi Univ, Fac Med, Dept Anesthesiol & Reanimat, TR-06500 Ankara, Turkey
[3] Diskapi Yildirim Bayezit Res & Educ Hosp, Dept Pathol, Ankara, Turkey
[4] Gazi Univ, Fac Med, Dept Clin Biochem, TR-06500 Ankara, Turkey
[5] Gazi Univ, Fac Pharm, Dept Pharmacol, TR-06500 Ankara, Turkey
来源：
ARCHIV DER PHARMAZIE | 2013年 / 346卷 / 06期
关键词：
Analgesic activity; Oxadiazole; Tetrazole; Thebaine; Thiadiazole; ANALGESICS;
D O I：
10.1002/ardp.201200451
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
In this study, we synthesized some novel N-(tetrazol-1H-5-yl)-6,14-endoethenotetrahydrothebaine 7-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, 1H NMR, 13C 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 LD50 dose for the most active compound 12 was determined.
引用
收藏
页码：455 / 462
页数：8
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