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 S., ÜNAL Y., Pamir O., Yilmazer D., KURTİPEK Ö., KAVUTÇU M., ...More

ARCHIV DER PHARMAZIE, vol.346, no.6, pp.455-462, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 346 Issue: 6
  • Publication Date: 2013
  • Doi Number: 10.1002/ardp.201200451
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.455-462
  • Keywords: Analgesic activity, Oxadiazole, Tetrazole, Thebaine, Thiadiazole, ANALGESICS
  • Gazi University Affiliated: Yes

Abstract

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.