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

Abstract

Thiazolidinedione derivatives are potential antidiabetic drugs that bind and activate peroxisome proliferator activated receptor gamma (PPAR gamma), which is a member of the nuclear hormone receptor superfamily and enhances insulin sensitivity. In an effort to develop a novel and effective thiazolidinclione 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 PPARy and inhibit LIPS-induced NO production were evaluated.