Ex-chiral pool synthesis and pharmacological aspects of 3-pyrrolidinylisoxazoles.
Employing the dopamine autoreceptor agonist (-)-3-PPP (3) as well as the cholinergic receptor ligands 4 and 5 as lead compounds the 3-pyrrolidinylisoxazoles 2a,b as well as its optical antipodes ent 2a,b were synthesized from (R)-aspartic acid (6) and (S)-aspartic acid (ent-6), respectively. Pharmacological properties of the target compounds were evaluated employing dopamine D2 receptor binding studies and functional experiments on muscarinic M2 receptors.
Thomas
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C
Institut für Pharmazie und Lebensmittelchemie der Universität Erlangen-Nürnberg, Germany.
Ohnmacht
U
U
Zahn
K
K
Mohr
K
K
Gmeiner
P
P
D000818:Animals; D001667:Binding, Competitive; D002417:Cattle; D006168:Guinea Pigs; D066298:In Vitro Techniques; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D009206:Myocardium / Q000378:metabolism; D017072:Neostriatum / Q000378:metabolism; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011869:Radioligand Assay; D043585:Receptor, Muscarinic M2; D017448:Receptors, Dopamine D2 / Q000378:metabolism*; D011976:Receptors, Muscarinic / Q000378:metabolism*; D013237:Stereoisomerism
C119603:3-methyl-5-(1-methyl-3-pyrrolidinyl)isoxazole; C119604:3-methyl-5-(1-propyl-3-pyrrolidinyl)isoxazole; D007555:Isoxazoles; D008024:Ligands; D011759:Pyrrolidines; D043585:Receptor, Muscarinic M2; D017448:Receptors, Dopamine D2; D011976:Receptors, Muscarinic