title: Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRalpha agonists.
abstract: Riccardin C, a nuclear receptor LXRalpha selective agonist, is an 18-membered macrocyclic bisbibenzyl isolated from several liverworts. Synthesis of riccardin C and its seven O-methylated derivatives was accomplished. The synthetic sequence highlights an intramolecular Suzuki-Miyaura coupling in the formation of the 18-membered biaryl linkage present in riccardin C. The structure-activity relationship of these compounds suggests that all of the phenolic hydroxy groups present in riccardin C are essential for the activation of LXRalpha.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Hioki
authors.forename: Naoki
authors.initials: N
authors.lastname: Shima
authors.forename: Kota
authors.initials: K
authors.lastname: Kawaguchi
authors.forename: Kenich
authors.initials: K
authors.lastname: Harada
authors.forename: Miwa
authors.initials: M
authors.lastname: Kubo
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Esumi
authors.forename: Tomoko
authors.initials: T
authors.lastname: Nishimaki-Mogami
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Sawada
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Hashimoto
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Asakawa
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Fukuyama
mesh_terms: D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D000071518:Liver X Receptors; D008956:Models, Chemical; D015394:Molecular Structure; D057093:Orphan Nuclear Receptors / Q000037:antagonists & inhibitors*; D019800:Phenol / Q000737:chemistry; D013053:Spectrophotometry / Q000379:methods; D013329:Structure-Activity Relationship
chemical_list: D004988:Ethers, Cyclic; D000071518:Liver X Receptors; C000605213:NR1H3 protein, human; D057093:Orphan Nuclear Receptors; C505660:riccardin C; D019800:Phenol