Synthesis and biological activity of 5-{4-[2-(methyl-p-substituted phenylamino)ethoxy]benzyl}thiazolidine-2,4-diones.

Thiazolidinedione derivatives are potential antidiabetic drugs that bind and activate peroxisome proliferator activated receptor gamma (PPARgamma), which is a member of the nuclear hormone receptor superfamily and enhances insulin sensitivity. In an effort to develop a novel and effective thiazolidindione derivative, 5-{4-[2-(methyl-p-substituted phenylamino) ethoxy] benzyl} thiazolidine-2,4-diones 7 have been prepared by Mitsunobu reaction of the hydrophobic segment, methyl-p-substituted phenylaminoethanol 4 with hydroxybenzylthiazolidinedione 5 and their ability to activate PPARgamma and inhibit LPS-induced NO production were evaluated.