Affiliation:
1. School of Pharmacy, Liverpool Polytechnic, Byrom Street, Liverpool L3 3AF, U.K.
Abstract
Abstract
The preparation and stereochemical characterization of all three isomeric forms of 4-acetoxy-1,2,6-trimethyl-4-phenylpiperidine is described. Of these, only the t-2-Me,c-6-Me,r-4-OCOMe isomer was an effective analgesic in mice (2·3 × pethidine) as judged by the hot-plate test. The results, together with reported data, demonstrate the potency raising effects of axial methyl α- to nitrogen and the lowering action of equatorial α-methyl substituents in reversed esters of pethidine.
Publisher
Oxford University Press (OUP)
Subject
Pharmaceutical Science,Pharmacology
Cited by
20 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献
1. Multi-component Reactions for the Synthesis of Biologically Relevant Molecules Under Environmentally Benign Conditions;Current Organic Chemistry;2021-11-01
2. Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives;Saudi Journal of Biological Sciences;2019-05
3. Synthesis of novel pyridine-connected piperidine and 2H-thiopyran derivatives and their larvicidal, nematicidal, and antimicrobial activities;Journal of the Mexican Chemical Society;2019-04-23
4. Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 3-Chloro-3-methyl-r(2),c(6)-bis(p-methoxyphenyl)piperidin-4-one;Journal of Chemical Crystallography;2019-01-02
5. Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate;Zeitschrift für Kristallographie - Crystalline Materials;2016-05-12