Effect of .beta.-alkyl substitution on D-1 dopamine agonist activity: absolute configuration of .beta.-methyldopamine

Journal of Medicinal Chemistry
1987.0

Abstract

beta-Methyldopamine and its enantiomers and racemic beta-phenyldopamine were synthesized and evaluated for dopamine D-1 agonist activity. In the dopamine-sensitive adenylate cyclase assay, beta-phenyldopamine had about one-sixth the activity of dopamine. Racemic beta-methyldopamine was less potent. The absolute configuration of beta-methyldopamine was determined to be R-(+) and S-(-). Evaluation of (R)-(+)- and (S)-(-)-beta-methyldopamine revealed no enantioselectivity for stimulation of adenylate cyclase.

Knowledge Graph

Similar Paper

Effect of .beta.-alkyl substitution on D-1 dopamine agonist activity: absolute configuration of .beta.-methyldopamine
Journal of Medicinal Chemistry 1987.0
Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine
Journal of Medicinal Chemistry 1982.0
Synthesis and Pharmacology of 6-Substituted Benztropines:  Discovery of Novel Dopamine Uptake Inhibitors Possessing Low Binding Affinity to the Dopamine Transporter
Journal of Medicinal Chemistry 2005.0
Conformationally defined adrenergic agents. 5. Resolution, absolute configuration, and pharmacological characterization of the enantiomers of 2-(5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthyl)imidazoline: a potent agonist at .alpha.-adrenoceptors
Journal of Medicinal Chemistry 1987.0
Synthesis and dopaminergic properties of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine, a potent and selective dopamine D4 receptor ligand
Bioorganic & Medicinal Chemistry Letters 2001.0
Asymmetric Synthesis and Pharmacology of Methylphenidate and Its Para-Substituted Derivatives
Journal of Medicinal Chemistry 1998.0
N-Alkyl derivatives of (.+-.)-.alpha.-methyldopamine
Journal of Medicinal Chemistry 1979.0
(.alpha.S)-erythro-.alpha.-Methylepinephrine: preparation and stereoselective binding to adrenergic receptors in rat forebrain
Journal of Medicinal Chemistry 1981.0
Synthesis and dopaminergic activity of 2-substituted octahydrobenzo[f]quinolines
Journal of Medicinal Chemistry 1989.0
Synthesis, absolute configuration, stereoselectivity, and receptor selectivity of (.alpha.R,.beta.S)-.alpha.,.beta.-dimethylhistamine. A novel highly potent histamine H3 receptor agonist
Journal of Medicinal Chemistry 1992.0