Sulfonyliminoimidazolidines. A new class of oral hypoglycemic agents. 1. 1-[[p-[2-(acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines.
A series of 1-[[p-[2-(acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines has been synthesized. Compounds from this new class of oral hypoglycemic agents lower blood glucose in normal and in streptozotocin-diabetic rats. Potent analogues were obtained by modification of the acyl residue. 1-[[p-[2-(Crotonylamino)ethyl]phenyl]-sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (44) turned out to be the most potent compound in the normal rat (20 times tolbutamide), and 1-[[p-[2-(5-methylisoxazole-3-carboxamido)ethyl]phenyl]sulfonyl]-3-cyclohexyl-2-imino-imidazolidine (30) displayed the highest potency in the diabetic rat (similar to phenformin).
D000818:Animals; D001681:Biological Assay; D001786:Blood Glucose / Q000032:analysis; D003921:Diabetes Mellitus, Experimental / Q000097:blood; D007004:Hypoglycemic Agents / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000138:chemical synthesis* / Q000494:pharmacology
D001786:Blood Glucose; D007004:Hypoglycemic Agents; D007093:Imidazoles; D007202:Indicators and Reagents; D013450:Sulfones