BETA-ADRENERGIC BLOCKING AGENTS .6. PRONETHALOL AND PROPRANOLOL ANALOGS WITH ALKYL SUBSTITUENTS IN ALKANOL SIDE CHAIN

Analogs of pronethalol (20) and propranolol (21) with substituents in the amiuoalkanol side chain have been synthesized. Adrenergic β-receptor blocking potency was generally reduced by substituting in the side chain. The erythro isomer of 2-isopropylamino-1-(2-naphthyl)-1-propanol was three times more potent than the threo isomer. Ethyl 2-amino-3-(ethoxyearbonylmethylamino)-3-(2-naphthyl)propionate (27) and 3-ethoxycarbonyl-2-(2-naphthyl)piperazin-5-one (28), obtained as by-products, were formed by self-condensation of the azomethine derived from 2-naphthaldehyde and glycine ethyl ester. © 1969, American Chemical Society. All rights reserved.