Synthesis and blood pressure lowering activity of benzylic ethers of 2-diethylaminoethanol and a related diamine.
Based upon the unpublished finding that 3'-hydroxy-4'-(beta-diethylaminoethoxy)-3',4'-dihydroseselin possessed a potent blood pressure lowering effect in the cat at a dose of 1 mg/kg, the present study examined the activities of several related compounds. These compounds were derived by dissection of the parent compound to give four benzylic ethers of 2-diethylaminoethanol and a diamine, derived by replacing the ether oxygen of the parent compound with an N--CH3 function. The simplest compounds were the benzyl and 2,6-dimethoxybenzyl ethers of the aminoalcohol. Closely related to the benzyl compound was a congener with a hydroxymethyl group on the benzylic carbon. The beta-diethylaminoethyl ether of 4-chromanol was the most complex of the ethers. The blood pressure measurements were carried out on male cats and compared to papaverine hydrochloride as a standard. In all cases, the most potent blood pressure lowering activity resided in the parent compound, which was not greatly superior to the diamine but substantially more active than the other compounds.
D000818:Animals; D001593:Benzyl Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D001794:Blood Pressure / Q000187:drug effects*; D002415:Cats; D003864:Depression, Chemical; D003959:Diamines / Q000138:chemical synthesis / Q000494:pharmacology; D004983:Ethanolamines / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D010208:Papaverine / Q000494:pharmacology
D001593:Benzyl Compounds; D003959:Diamines; D004983:Ethanolamines; D010208:Papaverine