title: Synthesis of dihydrofuran-fused perhydrophenanthrenes having a phenolic hydroxyl group as a novel anti-Alzheimer's disease agent.
abstract: As a part of our research program on developing novel anti-Alzheimer's disease medicines, several dihydrofuran-fused perhydrophenanthrenes (DFs) possessing a phenolic hydroxyl group were found to exhibit potent dendritic and axonal regeneration activities. Introduction of a methoxy group into the perhydrophenanthrene skeleton was successfully achieved via a PhI(OAc)(2)-mediated phenolic oxidation of a benzocyclobutene nucleus and subsequent tandem intramolecular electrocyclic reactions based on o-quinodimethane chemistry. We could reveal that a new methoxy derivative having a phenolic hydroxyl group exerted the most significant effects on the dendritic and axonal extensions in the damaged neurons, among DFs examined in this study.
authors.affiliation: Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Sugimoto
authors.forename: Kosuke
authors.initials: K
authors.lastname: Tamura
authors.forename: Naoki
authors.initials: N
authors.lastname: Ohta
authors.forename: Chihiro
authors.initials: C
authors.lastname: Tohda
authors.forename: Naoki
authors.initials: N
authors.lastname: Toyooka
authors.forename: Hideo
authors.initials: H
authors.lastname: Nemoto
authors.forename: Yuji
authors.initials: Y
authors.lastname: Matsuya
mesh_terms: D000544:Alzheimer Disease / Q000188:drug therapy*; D002396:Catechols / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D006801:Humans; D008956:Models, Chemical; D015394:Molecular Structure; D009502:Neutrons; D010100:Oxygen / Q000737:chemistry; D010616:Phenanthrenes / Q000737:chemistry*; D019800:Phenol / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry
chemical_list: D002396:Catechols; D010616:Phenanthrenes; D010636:Phenols; D019800:Phenol; C034221:catechol; D010100:Oxygen