Yuji Matsuya

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Organization: University of Toyama

Department: Graduate School of Medicine and Pharmaceutical Sciences

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Organic Chemistry

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Chemicals
References

Highly Efficient Access to Both Geometric Isomers of Silyl Enol Ethers: Sequential 1,2-Brook/Wittig Reactions

Co-reporter:Dr. Yuji Matsuya;Kentaro Wada;Dr. Daishiro Minato ;Dr. Kenji Sugimoto

Angewandte Chemie International Edition 2016 Volume 55( Issue 34) pp:10079-10082

Publication Date(Web):

DOI:10.1002/anie.201604945

Abstract

Novel sequential 1,2-Brook/Wittig reactions were developed for the preparation of silyl enol ethers. This method enables highly selective preparation of both geometric isomers of glyoxylate silyl enol ethers, using aldehydes (E-selective) and tosylimines (Z-selective) as a Wittig electrophile. The salt-free conditions of this reaction system are likely to be advantageous for switching the selectivity. The optimal reaction conditions and generality of the reaction were investigated, and plausible explanations for the observed selectivity were also discussed.

Highly Efficient Access to Both Geometric Isomers of Silyl Enol Ethers: Sequential 1,2-Brook/Wittig Reactions

Co-reporter:Dr. Yuji Matsuya;Kentaro Wada;Dr. Daishiro Minato ;Dr. Kenji Sugimoto

Angewandte Chemie 2016 Volume 128( Issue 34) pp:10233-10236

Publication Date(Web):

DOI:10.1002/ange.201604945

Abstract

Synthesis of Denosomin–Vitamin D3 Hybrids and Evaluation of Their Anti-Alzheimer’s Disease Activities

Co-reporter:Kenji Sugimoto, Hisanari Yajima, Yusuke Hayashi, Daishiro Minato, Sayuri Terasaki, Chihiro Tohda, and Yuji Matsuya

Organic Letters 2015 Volume 17(Issue 23) pp:5910-5913

Publication Date(Web):November 20, 2015

DOI:10.1021/acs.orglett.5b03138

As an extension of previously conducted studies on developing an anti-Alzheimer’s disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D3-membrane-associated, rapid response steroid-binding protein (1,25D3-MARRS) pathway. The biological assay revealed that the hybridization of characteristic δ-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid β (Aβ)-damaged neurons.

Three-Component Domino Process for the Pyrrolizine Skeleton via [3+2]-Cycloaddition–Enamine Cyclization Triggered by a Gold Catalyst

Co-reporter:Kenji Sugimoto, Nozomi Yamamoto, Daisuke Tominaga, and Yuji Matsuya

Organic Letters 2015 Volume 17(Issue 5) pp:1320-1323

Publication Date(Web):February 20, 2015

DOI:10.1021/acs.orglett.5b00320

Pyrrolizines are bicyclic fused azaheterocycles with a bridgehead nitrogen contained in a core skeleton and are often found in biologically active compounds. Despite their importance, there have been few reports on concise and flexible syntheses of pyrrolizines. A novel one-pot, convergent method is described for pyrrolizines by simple mixing of iminoesters, acetylenes, and dipolarophiles in the presence of a cationic gold catalyst and an acid additive. This domino process affords multisubstituted pyrrolizines without handling unstable intermediates.

Stereoselective approach to potential scaffold of A-nor B-aromatic OSW-1 analogues via [4+2] cycloaddition of o-quinodimethane

Co-reporter:Bozhi Li, Seiji Masuda, Daishiro Minato, Dejun Zhou, Kenji Sugimoto, Hideo Nemoto, Yuji Matsuya

Tetrahedron 2014 70(26) pp: 3981-3987

Publication Date(Web):

DOI:10.1016/j.tet.2014.04.079

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

Co-reporter:Kenji Sugimoto, Kosuke Tamura, Chihiro Tohda, Naoki Toyooka, Hideo Nemoto, Yuji Matsuya

Bioorganic & Medicinal Chemistry 2013 Volume 21(Issue 15) pp:4459-4471

Publication Date(Web):1 August 2013

DOI:10.1016/j.bmc.2013.05.059

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.

Search for a novel SIRT1 activator: Structural modification of SRT1720 and biological evaluation

Co-reporter:Yuji Matsuya, Yuta Kobayashi, Sayumi Uchida, Yukihiro Itoh, Hideyuki Sawada, Takayoshi Suzuki, Naoki Miyata, Kenji Sugimoto, Naoki Toyooka

Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 17) pp:4907-4910

Publication Date(Web):1 September 2013

DOI:10.1016/j.bmcl.2013.06.070

Syntheses and biological evaluation of novel SRT1720 derivatives are described in search for new candidates of SIRT1 activator. Several parts of the SRT1720 structure, including piperazine moiety, quinoxaline ring on the amide group, and position of the amide function, were modified, and the assay results indicated that transfer of the ortho amide-substituent regarding to the imidazo[1,2-b]thiazole core onto the meta position resulted in improvement of SIRT1 activation ability. Modeling analyses of SRT1720 and the most potent derivative bound to model complex of SIRT1 with peptide substrate were also performed.

Synthesis and antitumor activity of des-AB analogue of steroidal saponin OSW-1

Co-reporter:Daishiro Minato, Bozhi Li, Dejun Zhou, Yasumi Shigeta, Naoki Toyooka, Hiroaki Sakurai, Kenji Sugimoto, Hideo Nemoto, Yuji Matsuya

Tetrahedron 2013 69(37) pp: 8019-8024

Publication Date(Web):

DOI:10.1016/j.tet.2013.06.105

Efficient Approach to 1,2-Diazepines via Formal Diazomethylene Insertion into the C–C bond of Cyclobutenones

Co-reporter:Kenji Sugimoto, Rie Hayashi, Hideo Nemoto, Naoki Toyooka, and Yuji Matsuya

Organic Letters 2012 Volume 14(Issue 13) pp:3510-3513

Publication Date(Web):June 21, 2012

DOI:10.1021/ol301474g

Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C–C bond of cyclobutenone.

Novel sequential 1,4-Brook rearrangement–Wittig reaction: new one-pot approach for silyl dienol ethers

Co-reporter:Yuji Matsuya, Azusa Koiwai, Daishiro Minato, Kenji Sugimoto, Naoki Toyooka

Tetrahedron Letters 2012 Volume 53(Issue 44) pp:5955-5957

Publication Date(Web):31 October 2012

DOI:10.1016/j.tetlet.2012.08.114

A novel one-pot synthetic method of silyl dienol ethers via 1,4-Brook rearrangement–Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.

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

Co-reporter:Kenji Sugimoto, Kosuke Tamura, Naoki Ohta, Chihiro Tohda, Naoki Toyooka, Hideo Nemoto, Yuji Matsuya

Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 1) pp:449-452

Publication Date(Web):1 January 2012

DOI:10.1016/j.bmcl.2011.10.127

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.

Syntheses of aza-analogues of macrosphelides via RCM strategy and their biological evaluation

Co-reporter:Kenji Sugimoto, Yuta Kobayashi, Ayana Hori, Takashi Kondo, Naoki Toyooka, Hideo Nemoto, Yuji Matsuya

Tetrahedron 2011 67(40) pp: 7681-7685

Publication Date(Web):

DOI:10.1016/j.tet.2011.08.014

Synthesis and anti-influenza virus activity of dihydrofuran-fused perhydrophenanthrenes with a benzyloxy-type side-chain

Co-reporter:Yuji Matsuya, Nozomi Suzuki, Shin-ya Kobayashi, Tatsuro Miyahara, Hiroshi Ochiai, Hideo Nemoto

Bioorganic & Medicinal Chemistry 2010 Volume 18(Issue 4) pp:1477-1481

Publication Date(Web):15 February 2010

DOI:10.1016/j.bmc.2010.01.014

As one of our ongoing research project concerning development of a novel anti-influenza virus agent, dihydrofuran-fused perhydrophenanthrenes were derivatized by means of Williamson ether synthesis and Suzuki–Miyaura cross coupling reactions. Newly synthesized compounds were subjected to evaluation of anti-influenza virus activity using influenza A/Aichi/2/68 (H3N2 subtype) virus strain by a plaque titration method. These investigations revealed that incorporation of benzyl-type ether substituents was effective for exerting the inhibition activity of influenza virus proliferation.Novel dihydrofuran-fused tetracyclic compounds (2) with a benzyl-type ether side-chain were found to exhibit potent anti-influenza virus activity comparable to the previously reported derivative 1.

Synthesis of Sominone and Its Derivatives Based on an RCM Strategy: Discovery of A Novel Anti-Alzheimer’s Disease Medicine Candidate “Denosomin”

Co-reporter:Yuji Matsuya, Yu-ichiro Yamakawa, Chihiro Tohda, Kiyoshi Teshigawara, Masashi Yamada and Hideo Nemoto

Organic Letters 2009 Volume 11(Issue 17) pp:3970-3973

Publication Date(Web):August 4, 2009

DOI:10.1021/ol901553w

Synthesis of sominone was achieved starting from dehydroepiandrosterone on the basis of an RCM strategy for the construction of a δ-lactone side chain. This synthetic protocol was applied for the synthesis of several analogous derivatives including 1-deoxy-24-norsominone (denosomin), which was revealed to exhibit notable bioactivities for new antidementia chemotherapy, exceeding the original natural compound sominone.

Design, Synthesis, and Biological Evaluation of Artificial Macrosphelides in the Search for New Apoptosis-Inducing Agents

Co-reporter:Yuji Matsuya Dr.;Yuta Kobayashi;Takanori Kawaguchi;Ayana Hori;Yuka Watanabe;Kentaro Ishihara;Kanwal Ahmed;Zheng-Li Wei;Da-Yong Yu;Qing-Li Zhao;Takashi Kondo Dr. ;Hideo Nemoto Dr.

Chemistry - A European Journal 2009 Volume 15( Issue 23) pp:5799-5813

Publication Date(Web):

DOI:10.1002/chem.200802661

Kinetically Controlled Ring-Closing Metathesis: Synthesis of a Potential Scaffold for 12-Membered Salicylic Macrolides

Co-reporter:Yuji Matsuya Dr.;Sho-ichi Takayanagi ;Hideo Nemoto Dr.

Chemistry - A European Journal 2008 Volume 14( Issue 17) pp:5275-5281

Publication Date(Web):

DOI:10.1002/chem.200800249

Abstract

For the synthesis of a 12-membered salicylic macrolide scaffold, ring-closing metathesis (RCM) of a ω-diene compound was planned. The stereochemical outcome of the RCM reaction changed depending on the type of Ru catalyst that was used; a “first-generation” Grubbs catalyst produced exclusively the E isomer and “second-generation” catalysts provided a mixture of the E and Z isomers under kinetic control (not thermodynamic control). Considerations for the E/Z selectivity are described.