Oxygen Isosteric Derivatives of 3-(3-hydroxyphenyl)-N-n-propylpiperidine

J Med Chem. 1992 Aug 7;35(16):3045-9. doi: 10.1021/jm00094a019.

Abstract

Some substituted 3-phenylmorpholines (10a-e,j,k) and 3-thienylmorpholines (10f,g), isosteres of 3-(3-hydroxy-phenyl)-N-n-propylpiperidine (3-PPP), were prepared and submitted to binding assays on D-2 dopaminergic and 5-HT1 and 5-HT2 serotonergic receptors, in comparison with 3-PPP and its analogue 3a,b. The results show the loss of D-2 affinity for all morpholines, while a certain activity was still observable for piperidine derivatives. Regarding the serotonergic affinity, only chloro and methoxy derivatives (10a-d) were moderately active on the 5-HT1A receptor, either when the substituent was in the C-2 or C-3 position, whereas no tested compounds showed affinity toward the 5-HT2 receptor.

MeSH terms

  • Animals
  • Brain / metabolism
  • Dopamine Agents / chemistry*
  • Dopamine Agents / metabolism
  • In Vitro Techniques
  • Ketanserin / metabolism
  • Mice
  • Oxygen / chemistry*
  • Piperidines / chemistry*
  • Piperidines / metabolism
  • Radioligand Assay
  • Rats
  • Rats, Inbred Strains
  • Receptors, Serotonin / metabolism
  • Spiperone / metabolism

Substances

  • Dopamine Agents
  • Piperidines
  • Receptors, Serotonin
  • Spiperone
  • Ketanserin
  • preclamol
  • Oxygen