Effect of beta-alkyl substitution on D-1 dopamine agonist activity: absolute configuration of beta-methyldopamine.
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.
Riggs
R M
RM
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
McKenzie
A T
AT
Byrn
S R
SR
Nichols
D E
DE
Foreman
M M
MM
Truex
L L
LL
D000262:Adenylyl Cyclases / Q000378:metabolism; D000818:Animals; D001552:Benzazepines / Q000494:pharmacology; D003846:Deoxyepinephrine / Q000494:pharmacology*; D004298:Dopamine / Q000031:analogs & derivatives* / Q000378:metabolism; D008958:Models, Molecular; D051381:Rats; D012160:Retina / Q000201:enzymology; D013237:Stereoisomerism
D001552:Benzazepines; D000262:Adenylyl Cyclases; D003846:Deoxyepinephrine; D004298:Dopamine