A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone and its PPAR activities

Title
A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone and its PPAR activities
Authors
고재영황후상진정욱한동엽이재환양인호신경진함정엽강헌중
Keywords
Nuclear receptor; PPAR α/δ dual agonist; Marine agonist
Issue Date
2010-10
Publisher
Bioorganic & medicinal chemistry letters
Citation
VOL 20, NO 20, 6017-6019
Abstract
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 α, γ dialkyl γ-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 EC50 values of 12 μM for mPPARα, 9 μM for mPPARδ and >100 μM for mPPARγ.
URI
http://pubs.kist.re.kr/handle/201004/38189
ISSN
0960-894X
Appears in Collections:
KIST Publication > Article
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