Chemistry and hypoglycemic activity of N[[(dialkylamino)alkoxy]phenyl]benzamidines

Article abstract of DOI:10.1021/jm00346a006

A series of N-[[(dialkylamino)alkoxy]phenyl]benzamidines was synthesized and evaluated for hypoglycemic activity in the glucose-primed rat. Structure-activity relationships indicated r117w1 =N¹-phenyl-N-[4[2-(diisopropylamino)-ethox]phenyl]benzamid ine that N'-phenyl-N-[2-(diisopropylamino)-ethoxy]phenyl]benzamidine hydrobromide, N'-(4-chlorophenyl)-N-[4-(diisopropylamino)ethoxy]phenyl]-bensamidine dihydrochloride, and N'-phenyl-N-[4-[(diisopropylamino)propoxy]phenyl]benzamidine dihydrobromide are some of the more interesting compounds. A comparison of these hypoglycemic agents with classical standards (tolazamide, phenformin, and buformin) in several experimental models showed that the benzamidines seem to combine in one molecule some of the biological activities of the β-cytotrophic sulfonylureas and some of the activities of the biguanides.