Chemistry of Functional Molecule (Imagawa Lab.)

Staff
Prof. Dr. Hiroshi Imagawa

Dr. Hirofumi Yamamoto

Dr. Yusuke Kasai

Research project
Research projects of our group are the creation of functional molecules based on the synthetic organic chemistry, and developments of novel catalytic reactions. The major aim of us is to contribute to the development of seed compound for drug discovery, and creation of useful materials having a novel function. In particular, we focus on the development of novel therapeutic agents to treat Alzheimer’s disease, the anticancer drugs based on an immunostimulating activity and anti-infective drugs, which were designed based on mechanism of bacterial toxin. The following projects are currently in progress.

1) Syntheses and mechanistic studies of biologically active natural products.

  • Synthetic study of neovibsanin derivatives
  • Synthesis of thallusin and its analogues

2) Design and syntheses of novel functional molecules for drug discovery.

  • Design and synthesis of novel phosphate ester analog as neutral sphingomyelinase inhibitors
  • Syntheses of TDCM analogues and their interleukin-6 level enhancement activity

3) Development of novel catalyst for organic synthesis.

  • Silaphenylmercuric triflate-catalyzed reactions

Publications

  1. M. Oda, H. Imagawa, R. Kato, K. Yabiku, T. Yoshikawa, T. Takemoto, H. Takahashi, H. Yamamoto, M. Nishizawa, J. Sakurai, M. Nagahama, Novel inhibitor of bacterial sphingomyelinase, SMY-540, developed based on three-dimensional structure analysis, J. Enzyme Inhib. Med. Chem., 2013,Ahead of Print 1-8.
  2. Yamamoto, M. Oda, M. Nakano, K. Yabiku, M. Shibutani, T. Nakanishi, M. Suenaga, M. Inoue, H. Imagawa, M. Nagahama, Y. Matsunaga, S. Himeno, K. Setsu, J. Sakurai, M. Nishizawa, Concise synthesis of a probe molecule enabling analysis and imaging of vizantin, H. Chem. Pharm. Bull. 2013, 61, 452–459.
  3. K. Yoshikawa, K. Koso, M. Shimomura, M. Tanaka, H. Yamamoto, H. Imagawa, S. Arihara, T. Hashimoto, Yellow pigments, fomitellanols A and B, and drimane sesquiterpenoids, cryptoporic acids P and Q, from fomitella fraxinea and their inhibitory activity against COX and 5-LO, Molecules, 2013, 18, 4181-4191.
  4. Development of Vizantin, a Safe Immunostimulant, based on the Structure-Activity Relationship of Trehalose-6,6’-Dicorynomycolate.Yamamoto, H.; Oda, M.; Nakano, M.; Watanabe, N.; Yabiku, K.; Shibutani, M.; Inoue, M.; Imagawa, H.; Nagahama, M.; Himeno, S.; Setsu, K.; Sakurai, J.; Nishizawa, M. J. Med. Chem. 2013, 56, 381–385.
  5. A Carbaboranylmercuric Salt-Catalyzed Reaction; Highly Regioselective Cycloisomerization of 1,3-Dienes. Yamamoto, H.; Sasaki, I.; Shiomi, S.; Yamasaki, N.; Imagawa, H. Org. Lett. 2012, 14, 2266-2269.
  6. Syntheses of Structurally-simplified and Fluorescently-labeled Neovibsanin Derivatives  and Analysis of their Neurite Outgrowth Activity in PC12 cells, H. Imagawa, H. Saijo, H. Yamaguchi, K. Maekawa, T. Kurisaki, H. Yamamoto, M. Nishizawa, M. Oda, M. Kabura, M. Nagahama, J. Sakurai,  M. Kubo, M. Nakai, K. Makino, M. Ogata, H. Takahashi, Y. Fukuyama, Bioorg. Med. Chem. Lett, 2011, 76, 9711-9719.
  7. An Efficient Pyrrole Synthesis via Silaphenylmercuric Triflate-Catalyzed Cyclization of Homopropargyl Azides, H. Yamamoto, I. Sasaki, M. Mitsutake, A. Karasudani, H. Imagawa, M. Nishizawa,  Synlett, 2011,  2815-2818.
  8. Intermolecular Amination of Allyl Alcohols with Sulfamates: Effective Utilization of Mercuric Catalyst. H. Yamamoto, E. Ho, I. Sasaki, M. Mitsutake, Y. Takagi, H. Imagawa, M. Nishizawa,  Eur. J. Org. Chem., 2011, 2417-2420.
  9. Synthesis and Evaluation of Novel Phosphate Ester Analogs as Neutral Sphingomyelinase Inhibitors Imagawa, H.; Oda, M.; Takemoto, T.; Yamauchi, R.; Yoshikawa,  T,;  Yamamoto, H.;  Nishizawa, M.; Takahashi, H.; Hashimoto, M.; Yabiku,  K.; Nagahama, M.: Sakurai, J. Bioorg. Med. Chem. Lett., 2010, 20,3868–3871.
  10. Hg(OTf)2-BINAPHANE-Catalyzed Enantioselective Anilino Sulfonamide Allyl Alcohol Cyclization. H. Yamamoto, E. Ho, K. Namba, H. Imagawa, M. Nishizawa, Chem. Eur. J. 2010, 16, 11271-11274.