Ko, Jaeyoung Hwang, Hoosang Chin, Jungwook Hahn, Dongyup Lee, Jaehwan Yang, Inho Shin, Kyoungjin Ham, Jungyeob Kang, Heonjoong 2024-01-20T18:31:05Z 2024-01-20T18:31:05Z 2021-09-05 2010-10-15 0960-894X https://pubs.kist.re.kr/handle/201004/131000 A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the alpha,gamma dialkyl gamma-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC(50) values of 12 mu M for mPPAR alpha, 9 mu M for mPPAR delta and > 100 mu M for mPPAR gamma. (c) 2010 Elsevier Ltd. All rights reserved. English Pergamon Press Ltd. ALPHA,GAMMA-SUBSTITUTED GAMMA-BUTYROLACTONES SAMARIUM(II) IODIDE AGONISTS A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone and its PPAR activities Article 10.1016/j.bmcl.2010.08.069 1 Bioorganic & Medicinal Chemistry Letters, v.20, no.20, pp.6017 - 6019 Bioorganic & Medicinal Chemistry Letters 20 20 6017 6019 scie scopus 000281963700013 2-s2.0-77956933869 Chemistry, Medicinal Chemistry, Organic Pharmacology & Pharmacy Chemistry Article ALPHA,GAMMA-SUBSTITUTED GAMMA-BUTYROLACTONES SAMARIUM(II) IODIDE AGONISTS Nuclear receptor PPAR alpha/delta dual agonist Marine agonist