96610-50-3Relevant academic research and scientific papers
Synthesis and analgesic activity of 1,3,3,4,4-substituted piperidines
Huegi,Maurer,Romer,Petcher
, p. 487 - 494 (2007/10/02)
A series of 1,3,3,4,4-substituted piperidines has been prepared by a regioselective lithium ethylacetate condensation with cis/trans 2-butenoic or 2-propenoic acid ethylester derivatives, therapy affording the propane dicarboxylic acid diethylesters which were subjected to a number of reactions to give the title compounds. Their analgesic, morphinomimetic and morphine-antagonistic properties were determined. X-ray analysis of the 4-(3-hydroxyphenyl)-piperidine confirmed the undesired equatorial phenyl conformer explaining the possible failure to show biological properties throughout the 4-methyl-4-phenyl series. Although no strong analygesia or morphine-antagonism was found in the 4,4-diphenyl-series either, some of these compounds possess binding affinities to the 3H-naloxone binding site comparable to the reference compound bremazocine and morphine. As of yet we can only speculate why compounds with a high affinity to the receptor neither show analgesia, nor antagonize morphine induced analgesia.
