Homologs of dopa, alpha-methyldopa, and dopamine as potential cardiovascular drugs.
Starting from 3,4-dimethoxyphenacyl bromide, 2-amino-4-(3,4-dihydroxyphenyl)butyric acid (homodopa) was synthesized in six steps. 5-Hydroxyhomodopa was similarly prepared. alpha-Methylhomodopa was synthesized in four steps from zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone]. alpha-Methylhomodopa showed no antihypertensive activity in the genetic hypertensive rat. Homodopa did not potentiate the behavioral effect of Dopa or inhibit Dopa decarboxylase. Homodopamine, unlike dopamine, did not increase renal blood flow in the dog.
D006916:5-Hydroxytryptophan / Q000494:pharmacology; D000818:Animals; D065105:Aromatic Amino Acid Decarboxylase Inhibitors; D001794:Blood Pressure / Q000187:drug effects; D001921:Brain / Q000201:enzymology; D001923:Brain Chemistry / Q000187:drug effects; D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004285:Dogs; D004298:Dopamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004299:Dopamine beta-Hydroxylase / Q000037:antagonists & inhibitors; D004357:Drug Synergism; D007668:Kidney / Q000098:blood supply; D008297:Male; D008750:Methyldopa / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D009206:Myocardium / Q000201:enzymology; D051381:Rats; D012039:Regional Blood Flow / Q000187:drug effects; D013329:Structure-Activity Relationship
D065105:Aromatic Amino Acid Decarboxylase Inhibitors; D008750:Methyldopa; D004295:Dihydroxyphenylalanine; D006916:5-Hydroxytryptophan; D004299:Dopamine beta-Hydroxylase; D004298:Dopamine