TY - JOUR
T1 - A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone and its PPAR activities
AU - Ko, Jaeyoung
AU - Hwang, Hoosang
AU - Chin, Jungwook
AU - Hahn, Dongyup
AU - Lee, Jaehwan
AU - Yang, Inho
AU - Shin, Kyoungjin
AU - Ham, Jungyeob
AU - Kang, Heonjoong
PY - 2010/10
Y1 - 2010/10
N2 - 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.
AB - 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.
KW - Marine agonist
KW - Nuclear receptor
KW - PPAR α/δ dual agonist
UR - https://www.scopus.com/pages/publications/77956933869
U2 - 10.1016/j.bmcl.2010.08.069
DO - 10.1016/j.bmcl.2010.08.069
M3 - Article
C2 - 20822906
AN - SCOPUS:77956933869
SN - 0960-894X
VL - 20
SP - 6017
EP - 6019
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 20
ER -
