Synthesis and neuropharmacological characterization of 2-O-substituted apomorphines.
We have synthesized novel 2-O-substituted apomorphines with both different lengths of lipophilic alkyl chains and alkyl chains carrying free hydroxyl groups. Two bis-apomorphines formed as side products of the reactions with diols were isolated and characterized as well. The neuropharmacological profile of all these new compounds were investigated with respect to their binding affinities and activities to dopamine D(2) and D(1) receptors. The obtained data pointed to the fact that, in the examination of dopaminergic activities of 2-substituted apomorphines, the lipophilicity of the substituent is more important than its spatial parameters.
Sipos
Attila
A
Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary. asipos@puma.unideb.hu
Csutorás
Csaba
C
Berényi
Sándor
S
Uustare
Ain
A
Rinken
Ago
A
D000818:Animals; D001058:Apomorphine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016466:CHO Cells; D002384:Catalysis; D006224:Cricetinae; D003412:Cricetulus; D008958:Models, Molecular; D015394:Molecular Structure; D009474:Neurons / Q000187:drug effects*; D017447:Receptors, Dopamine D1 / Q000378:metabolism; D017448:Receptors, Dopamine D2 / Q000378:metabolism; D013329:Structure-Activity Relationship
D017447:Receptors, Dopamine D1; D017448:Receptors, Dopamine D2; D001058:Apomorphine