Structure-activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer's disease agent

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

doi:10.1016/j.bmc.2013.05.059

Structure-activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer's disease agent

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

^*Corresponding author for this work

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

26 Scopus citations

Abstract

As an extended study on development of anti-Alzheimer's disease agent, we newly synthesized various dihydrofuran-fused perhydrophenanthrenes via o-quinodimethane chemistry. This study revealed that the introduction of carbon side-chain on 8-position or removal of the acetal moiety on 3-position arose a cytotoxicity on rat cortical neurons. On the other hand, the ethereal or thio-ethereal substituent on 8-position enhanced the elongation effect on Aβ-damaged neurons. The necessity of the cyano group on 10b position was also proved in this structure-activity-relationship study.

Original language	English
Pages (from-to)	4459-4471
Number of pages	13
Journal	Bioorganic and Medicinal Chemistry
Volume	21
Issue number	15
DOIs	https://doi.org/10.1016/j.bmc.2013.05.059
State	Published - 2013/08/01

Keywords

Benzocyclobutenes o-Quinodimethane
Dendritic regeneration activity
Perhydrophenanthrenes

ASJC Scopus subject areas

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

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10.1016/j.bmc.2013.05.059

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title = "Structure-activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer's disease agent",

abstract = "As an extended study on development of anti-Alzheimer's disease agent, we newly synthesized various dihydrofuran-fused perhydrophenanthrenes via o-quinodimethane chemistry. This study revealed that the introduction of carbon side-chain on 8-position or removal of the acetal moiety on 3-position arose a cytotoxicity on rat cortical neurons. On the other hand, the ethereal or thio-ethereal substituent on 8-position enhanced the elongation effect on Aβ-damaged neurons. The necessity of the cyano group on 10b position was also proved in this structure-activity-relationship study.",

keywords = "Benzocyclobutenes o-Quinodimethane, Dendritic regeneration activity, Perhydrophenanthrenes",

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

note = "Funding Information: This work was financially supported by the MEXT, KAKENHI, a Grant-in-Aid for Scientific Research (C: 19590099 ). ",

year = "2013",

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doi = "10.1016/j.bmc.2013.05.059",

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T1 - Structure-activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer's disease agent

AU - Sugimoto, Kenji

AU - Tamura, Kosuke

AU - Tohda, Chihiro

AU - Toyooka, Naoki

AU - Nemoto, Hideo

AU - Matsuya, Yuji

N1 - Funding Information: This work was financially supported by the MEXT, KAKENHI, a Grant-in-Aid for Scientific Research (C: 19590099 ).

PY - 2013/8/1

Y1 - 2013/8/1

N2 - As an extended study on development of anti-Alzheimer's disease agent, we newly synthesized various dihydrofuran-fused perhydrophenanthrenes via o-quinodimethane chemistry. This study revealed that the introduction of carbon side-chain on 8-position or removal of the acetal moiety on 3-position arose a cytotoxicity on rat cortical neurons. On the other hand, the ethereal or thio-ethereal substituent on 8-position enhanced the elongation effect on Aβ-damaged neurons. The necessity of the cyano group on 10b position was also proved in this structure-activity-relationship study.

AB - As an extended study on development of anti-Alzheimer's disease agent, we newly synthesized various dihydrofuran-fused perhydrophenanthrenes via o-quinodimethane chemistry. This study revealed that the introduction of carbon side-chain on 8-position or removal of the acetal moiety on 3-position arose a cytotoxicity on rat cortical neurons. On the other hand, the ethereal or thio-ethereal substituent on 8-position enhanced the elongation effect on Aβ-damaged neurons. The necessity of the cyano group on 10b position was also proved in this structure-activity-relationship study.

KW - Benzocyclobutenes o-Quinodimethane

KW - Dendritic regeneration activity

KW - Perhydrophenanthrenes

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ER -

Structure-activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer's disease agent

Abstract

Keywords

ASJC Scopus subject areas

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