Design and synthesis of benzimidazole-linked meta-substituted benzylidenes/benzyls as biologically significant new chemical entities

Article abstract of DOI:10.1080/00397911.2012.678461

meta-Linked thiazolidinedione (TZD)-and diethyl malonate (DEM)-based benzylidenes and methyl acetoacetate (MAA)-based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD-and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPARα/γ) in the management of type 2 diabetes: a move from glitazones to selective PPARγ modulators (SPPARγMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.