Synthesis of dihydrofuran-fused perhydrophenanthrenes having a phenolic hydroxyl group as a novel anti-Alzheimer’s disease agent

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 pe...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-01, Vol.22 (1), p.449-452
Main Authors: Sugimoto, Kenji, Tamura, Kosuke, Ohta, Naoki, Tohda, Chihiro, Toyooka, Naoki, Nemoto, Hideo, Matsuya, Yuji
Format: Article
Language:English
Subjects:
Alzheimer disease
Alzheimer Disease - drug therapy
Benzocyclobutenes
Biological and medical sciences
Catechols - chemistry
Chemistry, Pharmaceutical - methods
Drug Design
Humans
Medical sciences
Models, Chemical
Molecular Structure
Neuronal regeneration activity
neurons
Neutrons
o-Quinodimethane
oxidation
Oxygen - chemistry
Perhydrophenanthrenes
Pharmacology. Drug treatments
Phenanthrenes - chemistry
Phenol - chemistry
Phenolic oxidation
Phenols - chemistry
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Summary: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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2011.10.127