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Paper | Regular issue | Vol 71, No. 10, 2007, pp.2131-2154
Published online, 29th June, 2007
DOI: 10.3987/COM-07-11095
Design, Synthesis, and Evaluation of Tetrahydroquinoline-Linked Thiazolidinedione Derivatives as PPARγ Selective Activators

HyeSung Kim, HyoJin Gim, Mihi Yang, Jae-Ha Ryu, and Raok Jeon*

*College of Pharmacy, Sookmyung Women’s University, 52 Hyochangwon-Gil, Yongsan-Ku, Seoul 140-742, Korea

Abstract

A series of tetrahydroquinoline-linked thiazolidinediones was designed and synthesized and their peroxisome proliferator activated receptor-γ (PPARγ) agonistic activities were evaluated. A number of analogs were revealed to have significant PPARγ agonistic activity. Among these compounds, compound 1h possessing N-heptyl moiety was found to be the most active in PPARγ transactivation assay. Molecular modeling suggested that the heptyl group of 1h appropriately interacts with hydrophobic amino acid residues in the active site of PPARγ.