Synthesis and dopamine D2-like receptor binding affinity of substituted 5-phenyl-pyrrole-3-carboxamides.
A series of 5-p-substituted phenyl-pyrrole-3-carboxamide derivatives was designed as hybrid analogs of the dopamine D2-like 5-phenyl-pyrrole and heterocyclic carboxamide antipsychotics. The title compounds were synthesized and evaluated for dopamine D2-like receptor by means of [3H]YM-09151-2 receptor binding assay. The compound bearing a 1-ethyl-2-methyl-pyrrolidine moiety as the basic part of 5-phenyl-pyrrole-3-carboxamide derivative 1a together with its 2-chloro analog 1f were found to possess affinity in the low micromolar range. Substituted phenyl-pyrrolecarboxamides containing groups such as F, Cl, NO2, CH3, at the 4-position of the phenyl ring, gave ligands with lower D2-like affinity.
Pinna
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GA
Istituto di Chimica Farmaceutica e Tossicologica, Università di Sassari, Italy. pinger@ssmain.uniss.it
Curzu
M M
MM
Sechi
M
M
Chelucci
G
G
Maciocco
E
E
D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001549:Benzamides; D001667:Binding, Competitive / Q000187:drug effects; D002421:Caudate Nucleus / Q000187:drug effects / Q000378:metabolism; D015259:Dopamine Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D018492:Dopamine Antagonists; D066298:In Vitro Techniques; D008297:Male; D051381:Rats; D017207:Rats, Sprague-Dawley; D017448:Receptors, Dopamine D2 / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000577:Amides; D001549:Benzamides; D015259:Dopamine Agents; D018492:Dopamine Antagonists; D017448:Receptors, Dopamine D2; C030265:nemonapride