Casy A F, Huckstep M R
School of Pharmacy and Pharmacology, University of Bath, UK.
J Pharm Pharmacol. 1988 Sep;40(9):605-8. doi: 10.1111/j.2042-7158.1988.tb05318.x.
The preparation of analogues of fentanyl with para substituents in the anilino aromatic ring, anilino nitrogen separated from phenyl by methylene or bimethylene, and phenacyl replacing propionyl as the N-acyl substituent is reported. Although all para substituents examined depressed antinociceptive potency in rats, most analogues of this kind were more effective than morphine and the p-F, I, and Me derivatives were only a few-fold less active than fentanyl. Separation of anilino nitrogen from phenyl lowered potency with N-phenethyl analogues retaining reasonable levels of activity (greater than morphine). All the phenacyl analogues were of low potency or inactive. Diagnostic details of the mass spectra of analogues likely to be encountered as "designer drugs' are appended.
本文报道了在苯胺芳环上具有对位取代基、苯胺氮原子通过亚甲基或二亚甲基与苯基隔开且苯甲酰基取代丙酰基作为N - 酰基取代基的芬太尼类似物的制备。尽管所研究的所有对位取代基均降低了大鼠的抗伤害感受效能，但这类大多数类似物比吗啡更有效，并且对氟、碘和甲基衍生物的活性仅比芬太尼低几倍。苯胺氮原子与苯基的隔开降低了效能，而N - 苯乙基类似物保留了合理的活性水平（大于吗啡）。所有苯甲酰类似物的效能都很低或无活性。附录中给出了可能作为“设计药物”遇到的类似物的质谱诊断细节。
