Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity

Kazunori Motoshima; Minoru Ishikawa; Yuichi Hashimoto; Kazuyuki Sugita

doi:10.1016/j.bmc.2011.03.065

Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity

Kazunori Motoshima, Minoru Ishikawa, Yuichi Hashimoto, Kazuyuki Sugita

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

Introduction of an alkylcarboxylic acid unit, which is a partial structure of endogenous peroxisome proliferator-activated receptor (PPAR) ligands, into a phenethylphenylphthalimide skeleton, which possesses liver X receptor (LXR) antagonistic activity, afforded novel PPAR ligands. The results of structure-activity relationship analysis and docking studies led us to the potent PPAR agonists 13c-e. The absolute configuration of 13c-e affects the PPAR subtype selectivity.

Original language	English
Pages (from-to)	3156-3172
Number of pages	17
Journal	Bioorganic and Medicinal Chemistry
Volume	19
Issue number	10
DOIs	https://doi.org/10.1016/j.bmc.2011.03.065
Publication status	Published - 2011 May 15
Externally published	Yes

Keywords

Molecular design
Nuclear receptor
PPAR agonist
Subtype selectivity

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2011.03.065

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Motoshima, K., Ishikawa, M., Hashimoto, Y., & Sugita, K. (2011). Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity. Bioorganic and Medicinal Chemistry, 19(10), 3156-3172. https://doi.org/10.1016/j.bmc.2011.03.065

Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists : Relationship between absolute configuration and subtype selectivity. / Motoshima, Kazunori; Ishikawa, Minoru; Hashimoto, Yuichi; Sugita, Kazuyuki.

In: Bioorganic and Medicinal Chemistry, Vol. 19, No. 10, 15.05.2011, p. 3156-3172.

Research output: Contribution to journal › Article › peer-review

Motoshima, K, Ishikawa, M, Hashimoto, Y & Sugita, K 2011, 'Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity', Bioorganic and Medicinal Chemistry, vol. 19, no. 10, pp. 3156-3172. https://doi.org/10.1016/j.bmc.2011.03.065

Motoshima K, Ishikawa M, Hashimoto Y, Sugita K. Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity. Bioorganic and Medicinal Chemistry. 2011 May 15;19(10):3156-3172. https://doi.org/10.1016/j.bmc.2011.03.065

Motoshima, Kazunori ; Ishikawa, Minoru ; Hashimoto, Yuichi ; Sugita, Kazuyuki. / Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists : Relationship between absolute configuration and subtype selectivity. In: Bioorganic and Medicinal Chemistry. 2011 ; Vol. 19, No. 10. pp. 3156-3172.

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