L. Anker, B. Testa, H. Waterbeemd
Mar 16, 1983
Citations
0
Influential Citations
13
Citations
Journal
Helvetica Chimica Acta
Abstract
N-Aminoalkylbenzamides and N-aminoalkyl-o-methoxybenzamides have been prepared and examined for their pKa, log P and dopamine receptor affinity. The pKa 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.