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- Title
Basicity, Lipophilicity, and Lack of Receptor Interaction of N-Aminoalkylbenzamides and N-Aminoalkyl- o-anisamides as Model Compounds of Dopamine Antagonists.
- Authors
Anker, Lucien; Testa, Bernard; Van De Waterbeemd, Han; Bornand-Crausaz, Anne; Theodorou, Andreas; Jenner, Peter; Marsden, C. David
- Abstract
N-Aminoalkylbenzamides and N-aminoalkyl- o-methoxybenzamides have been prepared and examined for their p Ka, log P and dopamine receptor affinity. The p Ka values range from ca. 7.5 for the derivatives having a one-C-atom side-chain, to ca. 10.3 for the N-aminobutyl derivatives. These variations with chain length are satisfactoryly explained by a field model. The variations in (log P)-values as a function of chain length and substitution at the N-atom indicate the involvement of proximity and conformational effects. The complete inability of the compounds to displace 3H-spiperone and 3H-sulpiride from their specific rat striatal binding sites demonstrates the critical role of adequate aromatic substitution at positions 4 and 5.
- Publication
Helvetica Chimica Acta, 1983, Vol 66, Issue 2, p542
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19830660215