SYNTHESIS OF N-HETERYL-BETA-[(2-ALKOXYETHYL)OXY] BETA-[[2-(N,N-DIALKYLAMINO)ETHYL]OXY]ACETAMIDES AS POSSIBLE H-1-ANTIHISTAMINICS

The synthesis of beta-[2-(alkoxyethyl)oxy]- and beta-[[2-(N,N-dialkyla mino)ethyl] oxy]acetamides containing an N-heteryl moiety is reported. Three heteryl systems, 2-phenyl/methyl-3,4-dihydro-4-oxoquinazolin-3y l, 5-aryl-1,3,4-oxadiazol-2-yl, and 5-alkyl-1,3,4-thia- diazol-2-yl, w ere employed. Appropriate heterylamines were first converted into thei r respective chloroacetamides and then reacted with 2-alkoxyethanols/2 -(N,N-dialkylamino)ethanols in dry acetone in the presence of anhydrou s potassium carbonate to obtain the title compounds. Ten such new acet amides from each series were synthesized and characterized. Their in v itro antihistaminic activity was determined using the isolated guinea pig ileum method. The IC50 values of the compounds indicated correlati ons with their structural and electronic features.