European Journal of Medicinal Chemistry p. 507 - 517 (1990)
Update date:2022-08-04
Topics:
De Paulis
Hall
Kumar
Ramsby
Ogren
Hogberg
A number of substituted 2-methoxybenzamides, with and without 6-hydroxy groups, with 4-piperidinyl side-chains have been synthesized and evaluated for their antidopaminergic properties. The salicylamides were found to require a lipophilic N-substituent, like a benzyl group, for high affinity for the dopamine D-2 binding site in contrast to salicylamides with 2-pyrrolodinylmethyl side-chains. Furthermore, the influence of the aromatic substituents on the activity in the 2 series, ie 4-piperidinyl and 2-pyrrolidinylmethyl side-chains, was different. This was supported by a Hansch analysis, which could accomodate both phenolic and non-phenolic benzamides with 1-benzyl-4-piperidinyl side-chains. The activity is primarily dictated by electronic features rather than by steric and lipophilic properties. The QSAR equations were validated by the design and synthesis of a new 10-fold more active derivative. The 2 classes of benzamides with different side-chains are suggested to act on different binding sites or on different subtypes of the dopamine D-2 receptor.
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