Synthesis and testing the cardiocirculatory effects of N-(3'-methoxybenzamidomethyl)-D-norephedrine and analogous compounds

Abstract

Twenty-six substituted N-benzamidomethyl and 3 N-(diphenylacetamido)methyl amines were prepd. by coupling I groups (R1 = H or MeO; R2 = H, Me MeO, EtO, PrO, or Cl; R3 = H, MeO, or Cl) and Ph2CHCONHCH2 groups, resp., to the N atom of phenylethylamine, amphetamine, phenylethanolamine, norephedrine, ephedrine, norfenefrine, and noradrenaline. Tests on the isolated guinea pig heart showed that the desired sepn. of coronary-dilating and pos. inotropic properties was not achieved by any of the compds. Six compds., including N-(3'-methoxybenzamidomethyl)-D-norephedrine-HCl [59630-62-5], had combined pos. inotropic and coronary circulation-promoting effects; none was as active as the ref. compd., oxyfedrine [15687-41-9]. Five N-benzamidomethyl-beta -phenylalkanolamines, synthesized in the hope of obtaining long-acting pressor effects in vivo, showed no activity in this regard. The compds. were synthesized by reaction of Ph2CHCONHCH2Cl or the N-chloromethyl analogs of I with the catechol amines in the presence of Et3N as H+ acceptor.