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

Kenji Sugimoto; Kosuke Tamura; Naoki Ohta; Chihiro Tohda; Naoki Toyooka; Hideo Nemoto; Yuji Matsuya

doi:10.1016/j.bmcl.2011.10.127

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

Kenji Sugimoto, Kosuke Tamura, Naoki Ohta, Chihiro Tohda, Naoki Toyooka, Hideo Nemoto, Yuji Matsuya^*

^*Corresponding author for this work

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

32 Scopus citations

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.

Original language	English
Pages (from-to)	449-452
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2011.10.127
State	Published - 2012/01/01

Keywords

Benzocyclobutenes
Neuronal regeneration activity
Perhydrophenanthrenes
Phenolic oxidation
o-Quinodimethane

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2011.10.127

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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.",

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author = "Kenji Sugimoto and Kosuke Tamura and Naoki Ohta and Chihiro Tohda and Naoki Toyooka and Hideo Nemoto and Yuji Matsuya",

note = "Funding Information: This work was financially supported by the Ministry of Education, Culture, Sports, and Technology, Japan, the KAKENHI, a Grant-in-Aid for Scientific Research (C: 19590099). ",

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AU - Sugimoto, Kenji

AU - Tamura, Kosuke

AU - Ohta, Naoki

AU - Tohda, Chihiro

AU - Toyooka, Naoki

AU - Nemoto, Hideo

AU - Matsuya, Yuji

N1 - Funding Information: This work was financially supported by the Ministry of Education, Culture, Sports, and Technology, Japan, the KAKENHI, a Grant-in-Aid for Scientific Research (C: 19590099).

PY - 2012/1/1

Y1 - 2012/1/1

N2 - 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.

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KW - Benzocyclobutenes

KW - Neuronal regeneration activity

KW - Perhydrophenanthrenes

KW - Phenolic oxidation

KW - o-Quinodimethane

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

Abstract

Keywords

ASJC Scopus subject areas

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