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Synthetic Organic Chemistry for Drug Development(Chemistry)

Arisawa MitsuhiroProfessor

• Graduated from Faculty of Pharmacy, Department of Pharmaceutical Sciences, Chiba University
• Ph.D., Graduate School of Pharmaceutical Sciences, Osaka University

[Work Experience]
• Assistant Professor, Graduate School of Pharmaceutical Sciences & Faculty of Pharmaceutical Sciences, Chiba University
• Visiting Researcher, Department of Chemistry and Chemical Biology, Harvard University, U.S.A. (Overseas Research Fellowship, Ministry of Education, Culture, Sports, Science and Technology)
School Pharmacist, Chiba University
• Associate Professor, Graduate School of Pharmaceutical Sciences & Faculty of Pharmaceutical Sciences, Hokkaido University
• Associate Professor, Graduate School of Pharmaceutical Sciences & Faculty of Pharmaceutical Sciences, Osaka University

• Award for Encouragement and Promotion of Science, Pharmaceutical Society of Japan
• The Society of Synthetic Organic Chemistry, Japan Takeda Pharmaceutical Research Planning Award, Mitsui Chemicals Research Planning Award
• Osaka University Award, Osaka University President's Encouragement Award
• Nagase Science and Technology Promotion Foundation Nagase Science Promotion Award

Research theme

Design, synthesis, and evaluation of biologically active compounds

Although there are several departments that deal with life phenomena, the approach to life phenomena using organic chemistry is a field in which the Faculty of Pharmaceutical Sciences excels, and it is still an important research area even now that the number of modalities has increased. In this field, we are designing and synthesizing new compounds to overcome central nervous system diseases and cancer. By using organic chemistry, we can logically control not only the main biological activity but also the physical properties. Functional evaluation is conducted through joint research with the Faculty of Pharmacy, Faculty of Medicine, Faculty of Dentistry, pharmaceutical companies, and national laboratories.

Design, synthesis, and evaluation of functional molecules such as medical dyes

We are designing, synthesizing, and functionally evaluating medical dyes that can provide rapid and accurate information about pathological conditions in a living state. Specifically, we are involved in the development of near-infrared dyes and two-photon excitation dyes, and we are also developing new reactions to achieve this goal. The functional evaluation is done in collaboration with the Faculty of Pharmacy, Faculty of Science, chemical companies, and national laboratories.

Synthesis of Heterocyclic Compounds Using Organometallic Catalysts

Tryptophan, an essential amino acid, has an indole skeleton. Indole is a typical nitrogen-containing heterocyclic compound, and in general, heterocyclic compounds are structures that privilege binding to proteins, so many pharmaceuticals have heterocycles. In our field, we are developing new synthetic methods for heterocyclic compounds containing nitrogen, oxygen, sulfur, silicon, and boron using organometallic catalysts.

Development of environmentally friendly catalysts

A large amount of waste is generated behind the production of functional molecules such as pharmaceuticals. In this field, we are developing new catalysts, reactions, and synthesis methods that do not produce waste and are environmentally and hygienically friendly.

Representative achievements

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, 23, 8131-8137

Thermal [2+2]-Cycloaddition between Silyl Alkynes and Allenyl Phenols Followed by the Nucleophilic Addition of Water: Metal-Free and Economical Synthesis of Arylcyclobutenals
Shohei Ohno#, Ramon Francisco Avena#, Hiroshi Aoyama, Hiromichi Fujioka, Mitsuhiro Arisawa, Green Chem. 2020, 22, 1220-1228.

Ligand-free Suzuki–Miyaura coupling reaction of aryl chloride using a continuous irradiation type microwave and palladium nanoparticle catalyst: Effect of a co-existing solid
Makito Yamada, Yasunori Shio, Toshiki Akiyama, Tetsuo Honma, Yuuta Ohki, Naoyuki Takahashi, Kenichi Murai, Mitsuhiro Arisawa, Green Chem. 2019, 21, 4541-4549.

Ligand-Free Suzuki–Miyaura Coupling Using Ruthenium(0) Nanoparticles and a Continuously Irradiating Microwave System
Toshiki Akiyama, Takahisa Taniguchi, Nozomi Saito, Ryohei Doi, Tetsuo Honma, Yusuke Tamenori, Yuuta Ohki, Naoyuki Takahashi, Hiromichi Fujioka, Yoshihiro Sato, Mitsuhiro Arisawa, Green Chem. 2017, 19, 3357-3369.

Suzuki–Miyaura cross-coupling reactions using a low-leaching and highly recyclable gold-supported palladium material and two types of microwave equipments
Mohammad Al-Amin, Masayoshi Akimoto, Tsuyoshi Tameno, Yuuta Ohki, Naoyuki Takahashi, Naoyuki Hoshiya, Satoshi Shuto, Mitsuhiro Arisawa, Green Chem. 2013, 15, 1142-1145.

One-Pot Ring-Closing Metathesis (RCM)/1,3-Dipolar Cycloaddition by an Assisted Tandem Ruthenium Catalysis for the Synthesis of a Novel Dye of Isoindolo[2,1-a]quinoline Structure
Mitsuhiro Arisawa, Yuki Fujii, Hiroshige Kato, Takashi Matsumoto, Mika Ito, Hiroshi Abe, Yoshihiro Ito, Satoshi Shuto, Angew. Chem. Int. Ed. Engl. 2013, 52, 1003-1007. [Highlighted in SYNFACTS 2013, 270.]

Design and Synthesis of Indomethacin Analogues that inhibit P-glycoprotein and/or Multi-drug Resistant Protein without Cox Inhibitory Activity
Mitsuhiro Arisawa, Yayoi Kasaya, Tohru Obata, Takuma Sasaki, Tomonori Nakamura, Takuya Araki, Koujirou Yamamoto, Akito Sasaki, Akihito Yamano, Mika Ito, Hiroshi Abe, Yoshihiro Ito, Satoshi Shuto, J. Med. Chem. 2012, 55, 8152–8163.

Sulfur Modification of Au via Treatment with Piranha Solution Provides Low-Pd Releasing and Recyclable Pd Material, SAPd
Naoyuki Hoshiya, Masahiko Shimoda, Hideki Yoshikawa, Yoshiyuki Yamashita, Satoshi Shuto, Mitsuhiro Arisawa, J. Am. Chem. Soc. 2010, 132, 7270-7272. [Highlighted in SYNFACTS 2010, 1080.]

Cycloisomerization Promoted by the Combination of a Ruthenium Carbene Catalyst and Vinyloxytrimethylsilane, and its Application to the Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans
Yukiyoshi Terada, Mitsuhiro Arisawa, Atsushi Nishida, Angew. Chem. Int. Ed. Engl. 2004, 43, 4063-4067.

Selective Isomerization of Terminal Olefin Catalyzed by a Ruthenium Complex: A Novel Indole Synthesis via Ring-Closing Metathesis (RCM).
Mitsuhiro Arisawa, Yukiyoshi Terada, Masako Nakagawa, Atsushi Nishida, Angew. Chem. Int. Ed. Engl. 2002, 41, 4732-4734.