Studies on the Structure-Activity Relationship of Adrenergic β-Mimetic Benzylamine Derivatives. IV. Aryl-substituted 1-Aminotetralins and 1-Aminoindans

The synthesis and adrenergic activity of the stereoisomeric aryl-substituted 1-aminotetralins (3, 4, and 7) and 1-aminoindans (5 and 6), rigid structures related to the benzylamine derivatives (2), are presented. Among this series of compounds tested, trans-5, 6-dihydroxy-1-methylamino-2-(3, 4, 5-trimethoxyphenyl)-1, 2, 3, 4-tetrahydronaphthalene (3b) was the most active tracheal relaxing compound, which was approximately ten times as active as the corresponding cis isomer (4b) and about two times as active as 2b. The structure-activity relationship in this series is discussed.