A series of N4-imidoethyl derivatives of 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine as 5-HT1A receptor ligands: synthesis and structure-affinity relationships.
A series of unsubstituted and substituted succinimido, maleimido, and glutarimidoethyl derivatives of eltoprazine (3) was synthesized and tested for affinity for the 5-HT1A receptor in rat brain homogenates. The unsubstituted compounds have a moderate affinity for the receptor, while the affinity considerably increases by substitution at or enlargement of these cyclic ring systems. A good correlation was found between the inhibition constant Ki (expressed as pKi) and the lipophilicity (clogP). No correlation was observed between the pKi or pKi+ (local inhibition constant) and the basicity of the N4-nitrogen atom.
D017371:8-Hydroxy-2-(di-n-propylamino)tetralin / Q000378:metabolism; D000818:Animals; D001665:Binding Sites; D001921:Brain / Q000378:metabolism; D003500:Cyclization; D005625:Frontal Lobe / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D050356:Lipid Metabolism; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry*; D051381:Rats; D011985:Receptors, Serotonin / Q000378:metabolism*; D017366:Serotonin Receptor Agonists / Q000138:chemical synthesis* / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D010879:Piperazines; D011985:Receptors, Serotonin; D017366:Serotonin Receptor Agonists; C063828:eltoprazine; D017371:8-Hydroxy-2-(di-n-propylamino)tetralin