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Closed Access item Synthesis and opioid activity of new fentanyl analogs

Authors:Girón, Rocío
Abalo, Raquel
Goicoechea, Carlos
Martín, Maria Isabel
Callado, Luis F.
Cano, Carolina
Goya Laza, Pilar
Jagerovic, Nadine
Keywords:Fentanyl analog, Nociception, In vitro assay, Opioid receptor, New analgesics
Issue Date:19-Jul-2002
Citation:Life Sciences 71 : 1023–1034 (2002)
Abstract:Three new fentanyl analogs (compounds 3-4-5) have been synthesized and evaluated for antinociceptive properties using the writhing test. The analgesic property of the active compound, N-[1-phenylpyrazol-3-yl]-N-[1- (2-phenethyl)-4-piperidyl)] propenamide (compound 4), was tested using the hot plate test in mice. Its opioid agonistic activity was characterized using three isolated tissues: guinea pig ileum, mouse vas deferens, and rabbit vas deferens. Compound 4 was as effective as fentanyl or morphine and it showed less antinociceptive potency than fentanyl but it was more potent than morphine. The duration of the antinociception was similar to that of fentanyl. This compound inhibited the electrically evoked contractions of myenteric plexus-longitudinal muscle strips of guinea pig ileum and of mouse vas deferens but not those of rabbit vas deferens. These effects could be reversed by A selective antagonists (naloxone and/or CTOP) but not by the y selective antagonist naltrindole, thus indicating that the compound acted as a A opioid agonist. Finally, the binding data confirmed that compound 4 had high affinity and selectivity for the A-receptor
Publisher version (URL):http://dx.doi.org/10.1016/S0024-3205(02)01798-8
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