ABSTRACT
New 2,4-thiazolidinediones with aryl sulfonylurea moieties have been synthesized by condensing various substituted sulfonamides and 5-(isocyanatomethyl) thiazolidino-2,4-dione. The isocyanomethyl thiazolidinedione was obtained by using the Curtius rearrangement, starting from known 2,4-dioxo-5-thiazolidineacetic acid. The newly synthesized compounds have been evaluated for the antihyperglycemic activity in normal rats model and among these compounds showed significant antihyperglycemic activity in sucrose loaded rat model.
Subject(s)
Diabetes Mellitus/drug therapy , Hypoglycemic Agents/pharmacology , Sulfonylurea Compounds/chemistry , Thiazolidinediones/chemical synthesis , Thiazolidinediones/pharmacology , Animals , Blood Glucose/drug effects , Chemistry, Pharmaceutical/methods , Chromatography, Thin Layer/methods , Drug Design , Male , Models, Chemical , Rats , Rats, Sprague-Dawley , Sucrose/chemistry , Time FactorsABSTRACT
A convenient and scalable four-step novel route has been developed for the synthesis of rosiglitazone (8), an antidiabetic drug. This multistep route requires 4-fluoro benzaldehyde (4), 2,4-thiazolidinedione (6) and 2-chloro pyridine (1) as key reactants and gives overall better yield of rosiglitazone. In addition, some steps have been accelerated, which leads to an overall time saving of 10h.
