N-Aralkyl substitution of 2-amino-5,6- and -6,7-dihydroxy-1,2,3,4-tetrahydronaphthalenes. 2. Derivatives of a hypotensive-positive inotropic agent

• Published in: Journal of medicinal chemistry Vol. 25; no. 3; pp. 326 - 328
• Main Authors: Stout, David M, Gorczynski, Richard J
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01.03.1982
• Subjects: Animals; Antihypertensive Agents - chemical synthesis; Cardiotonic Agents - chemical synthesis; Chemical Phenomena; Chemistry; Dogs; Heart Rate - drug effects; In Vitro Techniques; Naphthalenes - chemical synthesis; Organ Specificity; Tetrahydronaphthalenes - chemical synthesis; Tetrahydronaphthalenes - pharmacology
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00345a019

Seven derivatives of 2-[[2-(3,4-dihydroxyphenyl)-1-methylethyl]amino]-6,7-dihydroxy-1,2,3,4- tetrahydronaphthalene, an inotropic agent which also causes a decrease in blood pressure, were synthesized and tested for inotropic potency, cardioselectivity, and inotropic selectivity. The derivatives were designed to explore whether catechol moieties and rigid rotamers of dopamine are necessary for the activity which was found in the parent compound. The derivatives had phenolic functions in place of catechols, and they had phenethylamine in place of the tetrahydronaphthalene moiety. In no case was the profile of activity of the parent compound duplicated in the derivatives.