Opioid Properties of Some Derivatives of Pethidine Based on Tropane
- 1 October 1992
- journal article
- Published by Oxford University Press (OUP) in Journal of Pharmacy and Pharmacology
- Vol. 44 (10) , 787-790
- https://doi.org/10.1111/j.2042-7158.1992.tb03206.x
Abstract
The preparation of some tropane analogues of pethidine and its reversed ester, chiefly with preferred 3α-m-hydroxyphenyl chair conformations, is described. The former were secured from tropan-3-one in a sequence of reactions involving cyanide attack, hydrolysis, Grignard attack and then rearrangements. The reversed ester was obtained by treating tropan-3-one with lithium phenyl, followed by acylation. Configurational and conformational assignments follow from NMR analysis. The antinociceptive potencies of these compounds in mice are reported, and discussed in relation to non-phenolic congeners and the 4-arylpiperidine moiety of morphine.Keywords
This publication has 9 references indexed in Scilit:
- Phenolic analogues of diastereoisomeric 2-methyl reversed esters of pethidineJournal of Pharmacy and Pharmacology, 1989
- Synthesis and analgesic properties of N-substituted trans-4a-aryldecahydroisoquinolinesJournal of Medicinal Chemistry, 1988
- Opioid AnalgesicsPublished by Springer Nature ,1986
- Rotational conformation of the phenyl moiety in geminally substituted phenylcyclohexanes with equatorial phenylThe Journal of Organic Chemistry, 1985
- Analgesic activity of the epimeric tropane analogs of meperidine. Physical and pharmacological studyJournal of Medicinal Chemistry, 1975
- Conformational analysis of the tropane analogue of pethidine and related compounds by 1H NMR spectroscopyMagnetic Resonance in Chemistry, 1974
- Conformational analysis. LXXVIII. The conformation of phenylcyclohexane, and related molecules.Tetrahedron Letters, 1971
- Compounds Related to Pethidine--IV. New Genaral Chemical Methods of Increading the Analgesic Activity of PethidineJournal of Medicinal Chemistry, 1960
- Conformation of 3α-Phenyl-3β-tropanyl Phenyl Ketone; a Novel Nitrogen-Carbonyl InteractionJournal of the American Chemical Society, 1960