A series of compounds 1b-f, 2b-f, and 3b-f having an o-chlorobenzenesulfonamidic diuretic moiety variously linked to the nitrogen side chain of the beta-blocking (aryloxy)propanolamine pharmacophore were prepared and tested for their beta 1-adrenoceptor affinity. For all the active compounds, beta-blocking and diuretic activities were investigated in rats; the structure--activity relationships are discussed. Some of the compounds displayed varying levels of both properties and among these, compounds 1c and 2c have been chosen for further development.