103789-07-7Relevant academic research and scientific papers
Studies on antidiabetic agents. 11. Novel thiazolidinedione derivatives as potent hypoglycemic and hypolipidemic agents
Sohda,Mizuno,Momose,Ikeda,Fujita,Meguro
, p. 2617 - 2626 (2007/10/02)
In the course of further chemical modification of the novel antidiabetic pioglitazone (AD-4833, U-72, 107), a series of 5-[4-(2- or 4- azolylalkoxy)benzyl- or -benzylidene]-2,4-thiazolidinediones was prepared and evaluated for hypoglycemic and hypolipidemic activities in insulin-resistant, genetically obese, and diabetic KKA(y) mice. Replacement of the 2-pyridyl moiety of pioglitazone by a 2- or 4-oxazolyl or a 2- or 4-thiazolyl moiety greatly enhanced in vivo potency. The corresponding 5-benzylidene-type compounds, in which a methine was used as a linker between the benzene ring and the thiazolidinedione ring, also had potent biological activity. Among the compounds synthesized, 5-[4-[2-(5-methyl-2-phenyl-4- oxazolyl)ethoxy]benzyl]-2,4-thiazolidinedione (18) exhibited the most potent activity, more than 100 times that of pioglitazone. The synthesis and structure-activity relationships for this novel series of derivatives are detailed.
Thiazolidinedione derivatives, their production and use
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, (2008/06/13)
Thiazolidinedione derivatives of the general formula: STR1 [wherein R1 is hydrogen or a hydrocarbon residue or heterocyclic residue which may each be substituted; R2 is hydrogen or lower alkyl which may be substituted by hydroxyl group; X is an oxygen or sulfur atom; Z is a hydroxylated methylene or carbonyl; m is 0 or 1; n is an integer of 1 to 3; L and M represent independently a hydrogen atom or L and M combine with each other to cooperate jointly to form a linkage] and their salts, which are novel compounds, possess blood-glucose and blood-lipid lowering actions in mammals, and are of value as a therapeutic agent for diabetes and therapeutic agent for hyperlipemia.
