title: Synthesis, antidiabetic and hypolipidemic activities of new diethylamine and triethoxysilyl derivatives of tolbutamide on rats.
abstract: Tolbutamide (N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide, CAS 64-77-7, I) is the first generation of potassium channel blocker and sulfonylurea oral hypoglycemic drug that imparts marked blood glucose lowering effect in type 2 diabetes or non-insulin dependent diabetes mellitus (NIDDM) patients. In this study, I and its two new analogs with substituting butylamine side by 3-diethylamino-1-propylamine (3) and 3-triethoxysilyl-1-propylamine (4) were synthesized and their antidiabetic and hypolipidemic activities were evaluated applying known procedures, and compared with both I and glibenclamide (II, well known second-generation sulfonylurea antidiabetic drug). The results showed that these new drugs (III and IV) were more potent than I and II and it could be concluded that changing the amine side of I would produce more potentials in new drugs (III and IV) of the first generation, to be named as the third generation. Also investigations on hypoglycemic and lipid lowering effects of these drugs proved that IV could reduce glucose, triglyceride (TG) and a low density lipoprotein (VLDL) level in blood serum more than others (I-III), 16 days after STZ injection.
authors: Department of Chemistry, Faculty of Science, Islamic Azad University, P.O. Box: 31485-313, Karaj, Iran. a-ahmadi@kiau.ac.ir
authors: Abbas
authors: A
authors: Ahmadi
authors: Mohsen
authors: M
authors: Khalili
authors: Seyedsobhan
authors: S
authors: Seyedhoseyni
authors: Ehsan Maadi
authors: EM
authors: Roudsari
authors: Babak
authors: B
authors: Nahri-Niknafs
mesh_terms: D000818:Animals; D001786:Blood Glucose / Q000032:analysis; D003921:Diabetes Mellitus, Experimental / Q000097:blood / Q000139:chemically induced / Q000188:drug therapy*; D004048:Diethylamines / Q000737:chemistry; D005905:Glyburide / Q000494:pharmacology; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008079:Lipoproteins, VLDL / Q000097:blood; D008297:Male; D051381:Rats; D017208:Rats, Wistar; D012821:Silanes / Q000737:chemistry; D013311:Streptozocin; D014044:Tolbutamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D014280:Triglycerides / Q000097:blood
chemical_list: D001786:Blood Glucose; D004048:Diethylamines; D007004:Hypoglycemic Agents; D008079:Lipoproteins, VLDL; D012821:Silanes; D014280:Triglycerides; D013311:Streptozocin; C522569:triethoxysilane; D014044:Tolbutamide; C034281:diethylamine; D005905:Glyburide