研究者詳細 - 菅　誠治

論文 - 菅　誠治

分割表示 154 件中 41 - 60 件目／全件表示 >>

Synthesis and Properties of Dithieno-Fused 1,4-Azaborine Derivatives 査読

Koichi Mitsudo, Keisuke Shigemori, Hiroki Mandai, Atsushi Wakamiya, Seiji Suga

Organic Letters 20 ( 22 ) 7336 - 7340 2018年11月

Efficient Synthesis and Properties of [1]Benzothieno[3,2-b]thieno[2,3-d]furans and [1]Benzothieno[3,2-b]thieno[2,3-d]thiophenes 査読

Yuji Kurimoto, Koichi Mitsudo, Hiroki Mandai, Atsushi Wakamiya, Yasujiro Murata, Hiroki Mori, Yasushi Nishihara, Seiji Suga

ASIAN JOURNAL OF ORGANIC CHEMISTRY 7 ( 8 ) 1635 - 1641 2018年8月

Cu/Fe/O=PPh3-Catalyzed Etherification for the Synthesis of Aryl 3-Benzo[b]thienyl Ethers 査読

Koichi Mitsudo, Takuya Asada, Tomohiro Inada, Yuji Kurimoto, Hiroki Mandai, Seiji Suga

Chemistry Letters 47 ( 8 ) 1044 - 1047 2018年8月

Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1 '-Binaphthyl Unit: Importance of Amide Groups 査読

Hiroki Mandai, Kohei Hongo, Takuma Fujiwara, Kazuki Fujii, Koichi Mitsudo, Seiji Suga

Organic Letters 20 ( 16 ) 4811 - 4814 2018年8月

SYNTHESIS OF OXAZOLINES FROM N-ALLYLAMIDES USING AN ELECTROCHEMICALLY GENERATED ArS(ArSSAr)(+) POOL 査読

Yu Miyamoto, Naoya Mitani, Rina Yanagi, Shigenori Kashimura, Seiji Suga, Jun-ichi Yoshida, Kouichi Matsumoto

HETEROCYCLES 96 ( 8 ) 1373 - 1382 2018年8月

Miniaturization and Combinatorial Approach in Organic Electrochemistry 招待査読

Koichi Mitsudo, Yuji Kurimoto, Kazuki Yoshioka, Seiji Suga

CHEMICAL REVIEWS 118 ( 12 ) 5985 - 5999 2018年6月

Recent topics in enantioselective acyl transfer reactions with dialkylaminopyridine-based nucleophilic catalysts 招待査読

Hiroki Mandai, Kazuki Fujii, Seiji Suga

TETRAHEDRON LETTERS 59 ( 19 ) 1787 - 1803 2018年5月

Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations 招待査読

Koichi Mitsudo, Junya Yamamoto, Tomoya Akagi, Atsuhiro Yamashita, Masahiro Haisa, Kazuki Yoshioka, Hiroki Mandai, Koji Ueoka, Christian Hempel, Jun-ichi Yoshida, Seiji Suga

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 14 1192 - 1202 2018年5月

Combinatorial electrochemistry for organic synthesis 招待査読

Koichi Mitsudo, Yuji Kurimoto, Kazuki Yoshioka, Seiji Suga

CURRENT OPINION IN ELECTROCHEMISTRY 8 8 - 13 2018年3月

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts 査読

Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai, Seiji Suga

ADVANCED SYNTHESIS & CATALYSIS 359 ( 16 ) 2778 - 2788 2017年8月

Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of the Hydroxy Groups 査読

Hiroki Mandai, Hiroshi Yasuhara, Kazuki Fujii, Yukihito Shimomura, Koichi Mitsudo, Seiji Suga

JOURNAL OF ORGANIC CHEMISTRY 82 ( 13 ) 6846 - 6856 2017年7月

Development of Efficient and Effective Rate Acceleration Systems in Organocatalysis

Hiroki Mandai, Kazuki Fujii, Seiji Suga

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 75 ( 6 ) 632 - 649 2017年6月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：SOC SYNTHETIC ORGANIC CHEM JPN

Catalysts that can promote acyl transfer processes are important for enantioselective synthesis and their development has received significant attention in recent years. Very recently, we developed a method for the synthesis of chiral DMAP derivatives starting from an alpha-amino acid as a chiral source using a diastereoselective Ugi multicomponent reaction, and the protocol allowed us to access a variety of chiral catalysts in a one-step and one-pot manner. Such catalysts could be applied to various enantioselective acyl transfer reactions. In addition, we also reported a conceptually new type of kinetic resolution of secondary alcohols with a chiral phosphoric acid for the first time. Finally, we developed a binaphthyl-based chiral DMAP derivatives utilizing H-bonding interactions for enantioselective intra- and intermolecular acyl transfer reactions with high enantioselectivity. tert-Alcohol units of the catalyst play important roles in the acceleration of the rate of the reaction and achieving high enantioselectivity.

DOI： 10.5059/yukigoseikyokaishi.75.632

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Synthesis of 3-Benzo[b]thienyl 3-Thienyl Ether via an Addition-Elimination Reaction and Its Transformation to an Oxygen-Fused Dithiophene Skeleton: Synthesis and Properties of Benzodithienofuran and Its pi-Extended Derivatives 査読

Koichi Mitsudo, Yuji Kurimoto, Hiroki Mandai, Seiji Suga

Organic Letters 19 ( 11 ) 2821 - 2824 2017年6月

Rh-Catalyzed Dehydrogenative Cyclization Leading to Benzosilolothiophene Derivatives via Si-H/C-H Bond Cleavage 査読

Koichi Mitsudo, Seiichi Tanaka, Ryota Isobuchi, Tomohiro Inada, Hiroki Mandai, Toshinobu Korenaga, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

Organic Letters 19 ( 10 ) 2564 - 2567 2017年5月

Magnetic Attachment of Lipase Immobilized on Bacteriogenic Iron Oxide Inside a Microtube Reactor for the Kinetic Resolution of Secondary Alcohols 査読

Kyoko Mandai, Takehiro Fukuda, Yuki Miyazaki, Hideki Hashimoto, Hiroki Mandai, Tadashi Ema, Jun Takada, Seiji Suga

Synlett 28 ( 7 ) 805 - 810 2017年4月

AN INTRAMOLECULAR NUCLEOPHILE-CATALYZED ALDOL-LACTONIZATION (NCAL) REACTION OF S-ARYL-(E)-6-OXOHEX-2-ENETHIOATE WITH N,N-4-DIMETHYLAMINOPYRIDINE N-OXIDE 査読

Hiroki Mandai, Keita Shimowaki, Kohei Hongo, Koichi Mitsudo, Seiji Suga

HETEROCYCLES 94 ( 3 ) 492 - 502 2017年3月

Facile Synthesis of Naphthothiophenone Derivatives and Anthradithiophenedione via Friedel-Crafts Acylation and Their Fundamental Properties

Koichi Mitsudo, Takashi Murakami, Takuya Shibasaki, Tomohiro Inada, Hiroki Mandai, Hiromi Ota, Seiji Suga

SYNLETT 27 ( 16 ) 2327 - 2332 2016年10月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：GEORG THIEME VERLAG KG

Facile synthetic methods for constructing naphthothiophenone and its -extended derivatives were developed. Naphthothiophenone and anthradithiophenedione were synthesized by the S-acylation of thiol to form chlorothioformate and subsequent Friedel-Crafts acylation. A bromination reaction of naphthothiophenone and its application to Suzuki-Miyaura cross-coupling was also carried out. The fundamental physical properties of these compounds were also investigated.

DOI： 10.1055/s-0035-1562470

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Kinetic Resolution of Secondary Carbinols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1 '- Binaphthyl Unit: Hydrogen Bonding Affects Catalytic Activity and Enantioselectivity

Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai, Seiji Suga

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 89 ( 9 ) 1081 - 1092 2016年9月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：CHEMICAL SOC JAPAN

We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d' or DMAP. Hydrogen bonding between tert-alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.

DOI： 10.1246/bcsj.20160135

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Synthetic Terrein Inhibits Progression of Head and Neck Cancer by Suppressing Angiogenin Production

Akane Shibata, Soichiro Ibaragi, Hiroki Mandai, Toki Tsumura, Koji Kishimoto, Tatsuo Okui, Nur Mohammad Monsur Hassan, Tsuyoshi Shimo, Kazuhiro Omori, Guo-Fu Hu, Shogo Takashiba, Seiji Suga, Akira Sasaki

ANTICANCER RESEARCH 36 ( 5 ) 2161 - 2168 2016年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：INT INST ANTICANCER RESEARCH

Background/Aim: Head and neck cancers are the fifth most common cancer type worldwide, affecting more than half a million patients annually. Development of effective therapeutic drugs is, therefore, required for this type of disease. This study assessed the effects of synthetic terrein on head and neck cancer. Materials and Methods: Synthetic terrein was prepared by using the modified Altenhach's procedure. The effect of synthetic terrein on cell proliferation of head and neck cancer cells and HUVECs was assessed. Angiogenin secretion and ribosome biogenesis were examined by ELISA and silver staining of the nucleolar organizer region. A mouse xenograft model was prepared by inoculating mice with suspensions of cells of the human head and neck cancer cell line OSC-19 subcutaneously into the dorsal region of each mouse. Ki-67, CD31 and angiogenin expression in xenografted tumors was examined by immunohistochemistry. Results: Synthetic terrein inhibited the growth of various head and neck cancer cells. In addition, an in vivo experiment revealed that synthetic terrein inhibited a xenograft tumor growth in athymic mice. Immunohistochemical analysis revealed that expression of Ki-67, CD31 and ANG was down-regulated in synthetic terrein-treated tumors, compared to controls. Synthetic terrein suppressed the ANG secretion and ribosome biogenesis in cancer cells, and cell proliferation in vascular endothelial cells. Conclusion: The mechanism underlying the anti-tumor effects of synthetic terrein against head and neck cancer consists of the inhibition of both tumor cell proliferation and angiogenesis via the suppression of ANG production.

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Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions

Hiroki Mandai, Kazuki Fujii, Hiroshi Yasuhara, Kenko Abe, Koichi Mitsudo, Toshinobu Korenaga, Seiji Suga

NATURE COMMUNICATIONS 7 2016年4月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：NATURE PUBLISHING GROUP

Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts that are robust, efficient, recyclable and promote reactions with high enantioselectivity can be easily and cost-effectively prepared in significant quantities (that is, >10 g) has remained elusive. Here, we demonstrate that by attaching a binaphthyl moiety, appropriately modified to establish H-bonding interactions within the key intermediates in the catalytic cycle, and a 4-aminopyridyl unit, exceptionally efficient organic molecules can be prepared that facilitate enantioselective acyl transfer reactions. As little as 0.5 mol% of a member of the new catalyst class is sufficient to generate acyl-substituted all-carbon quaternary stereogenic centres in quantitative yield and in up to 98: 2 enantiomeric ratio (er) in 5 h. Kinetic resolution or desymmetrization of 1,2-diol can be performed with high efficiency and enantioselectivity as well.

DOI： 10.1038/ncomms11297

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