title: Synthesis and beta 1-, beta 2-adrenergic receptor binding studies of 4-acylamino-substituted phenoxypropanolamine and 5-acylamino-substituted naphthyloxypropanolamine derivatives.
abstract: The object of this study was to investigate the beta-adrenergic receptor binding affinity of 4-acylaminophenoxypropanolamine (10-15) and 5-acylaminonaphthyloxypropanolamine (21-24) derivatives, which were prepared from 4-aminophenol (5) and 5-amino-1-naphthol (16), respectively. The in vitro beta 1- and beta 2-adrenergic receptor binding affinities of the newly synthesized compounds were assessed in turkey erythrocyte membrane (beta 1) and lung homogenates of rats (beta 2). The binding affinities were compared with that of propranolol (3) (propranolol hydrochloride, CAS 318-98-9). The compound N-[5-(3-tert-butylamino-2-hydroxy-propoxy)-naphthalen-1-yl]-acetamide (22) has beta-adrenergic receptor affinity comparable with that of propranolol and shows selectivity to beta 1-adrenergic receptors.
authors.affiliation: University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh, India. dharampjindal@yahoo.co.in
authors.forename: Dharam Paul
authors.initials: DP
authors.lastname: Jindal
authors.forename: Mohane S
authors.initials: MS
authors.lastname: Coumar
authors.forename: Giancarlo
authors.initials: G
authors.lastname: Bruni
authors.forename: Paola
authors.initials: P
authors.lastname: Massarelli
mesh_terms: D000319:Adrenergic beta-Antagonists; D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects; D004082:Dihydroalprenolol; D004910:Erythrocyte Membrane / Q000187:drug effects / Q000378:metabolism; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D008168:Lung / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051381:Rats; D017207:Rats, Sprague-Dawley; D011943:Receptors, Adrenergic, beta / Q000187:drug effects*; D018342:Receptors, Adrenergic, beta-1 / Q000187:drug effects*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D014422:Turkeys
chemical_list: D000319:Adrenergic beta-Antagonists; D007202:Indicators and Reagents; D011943:Receptors, Adrenergic, beta; D018342:Receptors, Adrenergic, beta-1; C120358:adrenergic beta-4 receptor; D004082:Dihydroalprenolol