Synthesis and preliminary biological studies of 4- and 5-[2-hydroxy-3-(isopropylamino)propoxy]benzimidazoles: selective β2 adrenergic blocking agents

Abstract

Benzimidazoles carrying the 2-hydroxy-3-(isopropylamino)propoxy side chain at either the C-4 or C-5 ring positions were synthesized and investigated for .beta.-adrenergic blocking activity. Both compounds demonstrated .beta.2 selectivity when evaluated in guinea pig atrial and tracheal preparations. The C-4 isomer was 17 times more selective toward tracheal tissue, and its overall potency was roughly comparable to that of propranolol. .beta.2 selectivity of the C-5 isomer was minimal, with a potency about 1/100 that of propranolol.