title: Synthesis and structure-activity relationships of radicicol derivatives and WNT-5A expression inhibitory activity.
abstract: WNT-5A, a secretory glycoprotein, is related to the proliferation of dermal papilla cells. To develop a hair-growth stimulant, we have been searching for inhibitors of WNT-5A expression. We identified radicicol (1) as an active compound, and synthesized several radicicol derivatives. Among them, 6,7-dihydro-10alpha-hydroxy radicicol (31) was found to function as a new potent WNT-5A expression inhibitor with relatively low toxicity and excellent stability.
authors.affiliation: Medicinal Chemistry Laboratories, Taisho Pharmaceutical Co, Ltd, Saitama-shi, Saitama, Japan. h.shinonaga@po.rd.taisho.co.jp
authors.forename: Hideki
authors.initials: H
authors.lastname: Shinonaga
authors.forename: Toshiya
authors.initials: T
authors.lastname: Noguchi
authors.forename: Akiko
authors.initials: A
authors.lastname: Ikeda
authors.forename: Mari
authors.initials: M
authors.lastname: Aoki
authors.forename: Natsuko
authors.initials: N
authors.lastname: Fujimoto
authors.forename: Akira
authors.initials: A
authors.lastname: Kawashima
mesh_terms: D020405:Dermis / Q000166:cytology / Q000187:drug effects*; D015870:Gene Expression / Q000187:drug effects*; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D008958:Models, Molecular; D015394:Molecular Structure; D011518:Proto-Oncogene Proteins / Q000037:antagonists & inhibitors* / Q000235:genetics*; D013329:Structure-Activity Relationship; D051153:Wnt Proteins / Q000037:antagonists & inhibitors* / Q000235:genetics*; D000071818:Wnt-5a Protein
chemical_list: D018942:Macrolides; D011518:Proto-Oncogene Proteins; C085389:WNT5A protein, human; D051153:Wnt Proteins; D000071818:Wnt-5a Protein; C035359:monorden