title: 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.
abstract: 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 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.
authors: Faculty of Science, Department of Chemistry, Gazi University, Ankara, Turkey. syavuz@gazi.edu.tr
authors: Serkan
authors: S
authors: Yavuz
authors: Yusuf
authors: Y
authors: Ünal
authors: Özgür
authors: Ö
authors: Pamir
authors: Demet
authors: D
authors: Yılmazer
authors: Ömer
authors: Ö
authors: Kurtipek
authors: Mustafa
authors: M
authors: Kavutçu
authors: Mustafa
authors: M
authors: Arslan
authors: Mustafa
authors: M
authors: Ark
authors: Yılmaz
authors: Y
authors: Yıldırır
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D004195:Disease Models, Animal; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008297:Male; D009020:Morphine / Q000494:pharmacology; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010146:Pain / Q000188:drug therapy; D051381:Rats; D017208:Rats, Wistar; D013797:Thebaine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000700:Analgesics; D010069:Oxadiazoles; D013830:Thiadiazoles; D013797:Thebaine; D009020:Morphine