大阪大学薬学部 医薬合成化学分野

2021 Publications

I. Paper
1 Selective Reduction and Dihydroxylation of α,β-Unsaturated Esters in The Presence of Enals: One-Pot Synthesis of A 2,5-Disbstituted Tetrahydrofuran
Kenta Morita, Kenichi Murai, Mitsuhiro Arisawa, and Hiromichi Fujioka*
Heterocycles 2021103, 311-321.
DOI: 10.3987/COM-20-S(K)15

2 Conjugate Addition Reaction of Indole to Protected 2-Amino-1-Nitroethenes Mediated by Silica Gel
Kenichi Murai,* Shuji Miyazaki, and Hiromichi Fujioka*
Heterocycles 2021103, 459-464.
DOI: 10.3987/COM-20-S(K)5
3 Design, Synthesis, Physical Properties and Indoleamine 2, 3-Dioxygenase 1 Inhibitory Activity of Substituted Indole Derivatives with N-H, N-Metohymethyl, or N-Mehylthiomethyl Group toward Fragment-Based Drug Discovery
Kenta Hayami#, Yuichi Kuboki#, Katsumi Ohta, Bangzhong Lin, Megumi Fumimoto, Kazuto Nunomura, Jun-Ichi Haruta , Kenichi Murai, Hiromichi Fujioka, Akira Asai, and Mitsuhiro Arisawa*
# Equal contribution
Heterocycles 2021, 103, 511-525.
DOI: 10.3987/COM-20-S(K)35
4 Total Synthesis and Biological Evaluation of the Potent HIV Latency-Reversing Agent Ansellone A and its Analogues
Mizushi Yanagihara, Kenichi Murai*, Naoki Kishimoto, Towa Abe, Shogo Misumi, Mitsuhiro Arisawa*
Org. Lett. 2021, 23, 1720–1725.
DOI: 10.1021/acs.orglett.1c00151
5 Structure-activity Relationship of Indomethacin Derivatives as IDO1 Inhibitors
Tohru Obata, Sara Shiratani, Tomomi Nada, Yayoi Kasaya, Mitsuhiro Arisawa, Satoshi Shuto, Motohiro Tanaka
Anticancer Res. 2021, 41, 2287-2296.
DOI: 10.21873/anticanres.15004
6 Iridium-Catalyzed Isomerization/Cycloisomerization/Aromatization of N-Allyl-N-sulfonyl-o-(λ1-silylethynyl)aniline Derivatives to Give Substituted Indole Derivatives
Jiawei Qiu, Makoto Sako, Tomoyuki Tanaka, Tsuyoshi Matsuzaki, Tsunayoshi Takehara, Takeyuki Suzuki, Shohei Ohno, Kenichi Murai, Mitsuhiro Arisawa*
Org. Lett. 2021,  23, 4284–4288.
DOI: 10.1021/acs.orglett.1c01231
7

Revisiting Chiral Recognition Mechanism on Chicken Alpha 1-Acid Glycoprotein: Location of Chiral Binding Sites and Insight into Chiral Binding Mechanism
Jun Haginaka,* Taku Yamashita, Hirofumi Tsujino, and Mitsuhiro Arisawa
Separations 2021, 8, 73.
DOI: 10.3390/separations8060073

8 A New Bitterness Evaluation Index Obtained Using the Taste Sensor for 48 Active Pharmaceutical Ingredients of Pediatric Medicines
Honami Kojima, Toshio Kurihara, Miyako Yoshida, Tamami Haraguchi, Haruka Nishikawa, Saeri Ikegami, Takayoshi Okuno, Taku Yamashita, Junichi Nishikawa, Hirofumi Tsujino, Mitsuhiro Arisawa, Masaaki Habara, Hidekazu Ikezaki, Takahiro Uchida*
Chem. Pharm. Bull. 2021, 69, 537-547.
DOI: 10.1248/cpb.c20-01014
9 Chemo- and Enantioselective Hetero-coupling of Hydroxycarbazoles Catalyzed by a Chiral Vanadium(v) Complex
Makoto Sako, Keigo Higashida, Ganesh Tatya Kamble, Kevin Kaut, Ankit Kumar, Yuka Hirose, Dayang Zhou, Takeyuki Suzuki, Magnus Rueping, Tomohiro Maegawa, Shinobu Takizawa*, Hiroaki Sasai*
Org. Chem. Front. 2021, 8, 4878-4885.
DOI: 10.1039/D1QO00783A
10 Preparation of a Platinum Nanoparticle Catalyst Located Near Photocatalyst Titanium Oxide and Its Catalytic Activity to Convert Benzyl Alcohols to the Corresponding Ethers
Yuki Wada, Toshiki Akiyama, Kazuo Harada, Tetsuo Honma, Hiroshi Naka, Susumu Saito, Mitsuhiro Arisawa*
RSC Adv. 2021, 11, 22230–22237.
DOI: 10.1039/d1ra00988e
11 Carbon-Carbon Bond Formation Between Nitrogen-Containing Heterocyclic Carbene (NHC) Ligand on Ruthenium Carbene Catalysts and 1,4-Naphthoquinone via Intramo-lecular Carbon(sp3)-Hydrogen Bond Activation
Yuki Wada, Tsunayoshi Takehara, Takeyuki Suzuki, Satoshi Aoki, Takayuki Hibi, Makoto Sako, Hirofumi Tsujino, Yasuo Tsutsumi, Mitsuhiro Arisawa*
Organometallics 2021, 40, 2901-2908.
DOI: 10.1021/acs.organomet.1c00350
12 Design, Synthesis, and Monoamine Oxidase Inhibitory Activity of (+)-Cinchonaminone and Its Simplified Derivatives
Yuta Sato#, Naoko Oyobe#, Takao Ogawa, Sayo Suzuki, Hiroshi Aoyama, Tomonori Nakamura, Hiromichi Fujioka, Satoshi Shuto, Mitsuhiro Arisawa*
# Equal contribution
ACS Med. Chem. Lett. 2021, 12, 1464–1469.
DOI: 10.1021/acsmedchemlett.1c00310
13 Inhibitory Activity and Proposed Binding Model of γ-Glutamyl Cysteine, the Precursor of Glutathione, on Angiotensin Converting Enzyme
Chisato Okajima, Naoki Imakawa, Kazuya Nagano*, Masayoshi Arai, Mitsuhiro Arisawa, Misa Muraoka, Hirofumi Tsujino, Yoshihiko Hirata, Kazumasa Hirata*
BPB Reports 2021, 4, 116-119.
DOI: 10.1248/bpbreports.4.4_116
14 Product Selective Reaction Controlled by the Combination of a Palladium Nanoparticles, Continuous Microwave Irradiation, and a Co-existing Solid; Ligand-Free Buchwald–Hartwig Amination vs Aryne Amination
Makito Yamada, Ryousuke Ohta, Kazuo Harada, Tsunayoshi Takehara, Hitoshi Haneoka, Yosuke Murakami, Takeyuki Suzuki, Yuuta Ohki, Naoyuki Takahashi, Toshiki Akiyama, Natchanun Sirimangkalakitti, Makoto Sako, Kenichi Murai, Masayoshi Arai, Mitsuhiro Arisawa*
Green. Chem. 2021, 8131-8137.
DOI: 10.1039/D1GC01782A【Open Access】
15 Chemo- and Regioselective Cross-dehydrogenative Coupling Reaction of 3-Hydroxycarbazoles with Arenols Catalyzed by a Mesoporous Silica-supported Oxovanadium
Kengo Kasama, Kyohei Kanomata, Yuya Hinami, Karin Mizuno, Yuta Uetake, Toru Amaya, Makoto Sako, Shinobu Takizawa, Hiroaki Sasai, Shuji Akai*
RSC Adv. 2021, 11, 35342-35350.
DOI: 10.1039/D1RA07723F 【Open Access】
Ⅱ. Review
1 “ヘテロ原子が直接結合したオレフィンを反応点とする炭素環・ヘテロ環合成法;芳香環につながれた2つの多重結合間での反応”
大野 祥平, 有澤 光弘*
有機合成化学協会誌,Vol. 79, No.1 (2021), 22-33.
“Carbo─ and Heterocycle Syntheses via Reactions between Two Multiple Bonds; Involving Heteroatom─Substituted Unsaturated Bonds”
Shohei Ohno, Mitsuhiro Arisawa*
J. Synth. Org. Chem. Jpn. 2021, 79, 22-33.
DOI: 10.5059/yukigoseikyokaishi.79.22
2

Non-directed β- or γ-C(sp3)-H Functionalization of Saturated Nitrogen-containing Heterocycles
Shohei Ohno, Makoto Miyoshi, Kenichi Murai, Mitsuhiro Arisawa*
Synthesis 2021, 53, 2947-2960.
DOI: 10.1055/a-1483-4575

3 Recent Advances in Metal Nanoparticle-catalyzed Coupling Reactions Assisted by Microwave Irradiation
Makoto Sako, Mitsuhiro Arisawa*
Synthesis 2021, 53, 3513-3521.
DOI: 10.1055/a-1505-0916
4 C-F結合活性化によるジフルオロメチレン基の不斉非対称化
山田 真希人
ファルマシア, Vol. 57, No.6 (2021), 542.
DOI: 10.14894/faruawpsj.57.6_542
5 N-保護アミノ酸を配位子として用いた炭素(sp3)-水素結合活性化反応
吉岡 祥平
有機合成化学協会誌, Vol. 79, No. 7 (2021), 694-695.
DOI: 10.5059/yukigoseikyokaishi.79.694
6 アーヘン工科大学での研究と生活
佐古 真
Organometallic News, No. 3 (2021), 82-83.
https://kinka.or.jp/om/omnews_archive/2021_03.html
7 (注目の論文)分子から窒素を引っこ抜け!第二級アミンの分子骨格編集反応の開発
佐古 真
化学, Vol. 76, No. 10 (2021), 70-71.
https://www.kagakudojin.co.jp/book/b591529.html
Ⅲ. Winning Prize
1 第5回 Yoshida Prize Symposium Distinguished Lecture
有澤教授が国際有機化学財団(International Organic Chemistry Foundation; IOCF)第5回吉田賞シンポジウムで、Distinguished Lectureを受賞しました。
「Self-Assembled Multilayer-Stabilized Metal Nanoparticle Catalyst for Functional Molecular Synthesis: in-situ Metal Nanoparticle and Nanospace Simultaneous Organization」
https://iocf.sbchem.kyoto-u.ac.jp