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2011 Fiscal Year Final Research Report

Fluorinated Medicines : Drug Development based on Functional Groups

Research Project

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Project/Area Number 21390030
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Drug development chemistry
Research InstitutionNagoya Institute of Technology

Principal Investigator

SHIBATA Norio  名古屋工業大学, 大学院・工学研究科, 教授 (40293302)

Project Period (FY) 2009 – 2011
Keywords医薬品化 / 有機化学 / フッ素 / 創薬 / 不斉合成 / 生理活性物質
Research Abstract

We have developed the novel trifluoromethylation and monofluoromethylation reaction toward for drug development and the methods were applied to the synthesis of biologically attractive molecules.

  • Research Products

    (47 results)

All 2011 2010 2009

All Journal Article (45 results) (of which Peer Reviewed: 45 results) Presentation (2 results)

  • [Journal Article] Influence of New Fullerene Derivatives with Fluorocarbon Substituent on Performance of Polymer Solar Cells2011

    • Author(s)
      Ichiko Yamada, Manoj Pandey, Yasuhiko Hayashi, Norio Shibata, Tesuo Saga, Takeshi Torub
    • Journal Title

      Physics Procedia

      Volume: 14 Pages: 192-197

    • Peer Reviewed
  • [Journal Article] A New Synthetic Approach to Efavirenz through Enantioselective Trifluorome thylation by Using the Ruppert Prakash Reagent2011

    • Author(s)
      Hiroyuki Kawai, Takashi Kitayama, Etsuko Tokunaga, Norio Shibata
    • Journal Title

      Eur. J. Org. Chem

      Volume: 30 Pages: 5959-5961

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Chiral Trifluoromethylated Heliotridane via Highly Catalytic Asymmetric Frieder-Crafts Alkylation with ls-Trifluorome thylated Acrylates and Pyrroles2011

    • Author(s)
      Yiyong Hwang, Satoru Suzuki, Guokai Lin, Etsuko Tokunaga, Mo too Shire and Norio Shibata
    • Journal Title

      New. J. Chem

      Volume: 35 Pages: 2614-2621

    • Peer Reviewed
  • [Journal Article] AsymmetricAllylic Monofluorome thylationand Methylation of Morita-Baylis-Hillman Carbonates with FBSM and BSM by Cooperative Cinchona Alkaloid/FeCl2 Catalysis2011

    • Author(s)
      Tatsuya Furukawa, Jumper Kawazoe, wet Zhang, Takayuki Nishimine, Etsuko Tokunaga, Takashi Matsumoto, Dr. Mo too Shire, Prof. Norio Shibata
    • Journal Title

      Angew. Chem. Mt. Ed

      Volume: 50(41) Pages: 9684-9688

    • Peer Reviewed
  • [Journal Article] Organocatalyzed Regia and Enantioselective Allylic Trifluoromethylation of Morita-Baylis Hillman Adducts Using Ruppert Prakash Reagent2011

    • Author(s)
      Tatsuya Furukawa, Takayuki Nishimine, Etsuko Tokunaga, Kimiko Hasegawa, Mo too Shire, and Norio Shibata
    • Journal Title

      Org. Left

      Volume: 13(15) Pages: 3972-3975

    • Peer Reviewed
  • [Journal Article] Construction of Trifluorome thyl Bearing Quaternary Carbon Centers by Intramolecular Decarboxylative Allylation of a Trifluoromethyl 6-Keto Esters2011

    • Author(s)
      Norio Shibata, Satoru Suzukil, Tatsuya Furukawa, Hiroyuki Kawai, Etsuko Tokunaga, Zhe Yuan, Dominique Canard
    • Journal Title

      Adv. Synth. Catal

      Volume: 353(11-12) Pages: 2037-2041

    • Peer Reviewed
  • [Journal Article] A Characterization of Maternal and Developmental Toxicity in Rabbits and Mice2011

    • Author(s)
      Crystal J. J. Lee, Norio Shibata, Michael J. Wiley and Peter G. wellst
    • Journal Title

      Toxicol. Sci

      Volume: 122(1) Pages: 157-169

    • Peer Reviewed
  • [Journal Article] Cu Mediated Chemo-selective Trifluoromethylation of Benzyl Bromides using Shelf-stable Electrophilic Trifluoromethylating Reagents2011

    • Author(s)
      Hiroyuki Kawai, Tatsuya Furukawa, Yoshinori Nomura, Etsuko Tokunaga, and Norio Shibata
    • Journal Title

      Org. Left

      Volume: 13(14) Pages: 3596-3599

    • Peer Reviewed
  • [Journal Article] Trifluoromethylation of Aromatic Isoxazoles : Regia and Di istereoselective Route to 5-Trifluoromethyl-2-isoxazolines2011

    • Author(s)
      Hiroyuki Kawai, Kentaro Tachi, Etsuko Tokunaga, Dr. Motoo Shire, Prof. Norio Shibata
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 123(34) Pages: 7949-7952

    • Peer Reviewed
  • [Journal Article] In vive Formation of a Glutathione Conjugate Derived from Thalidomide in Humanized uPA-NOG Mice2011

    • Author(s)
      Hiroshi Yamazaki, Hiroshi Suemizu, She Igaya, Makiko Shimizu, Norio Shibata
    • Journal Title

      Chem. Res. Toxicol

      Volume: 24(3) Pages: 287-289

    • Peer Reviewed
  • [Journal Article] Robust Synthesis of Trifluoromethionine and Its Derivatives by Reductive Trifluoromethylation of Amino Acid Disulfides by CFsI/NaILiq. NH3 system2011

    • Author(s)
      Hiroyuki Yasui, Takeshi Yamamoto, Etsuko Tokunaga, Norio Shibata
    • Journal Title

      J Fluorine Chem

      Volume: 132(3) Pages: 186-189

    • Peer Reviewed
  • [Journal Article] A sterically Demanding Electrophilic Fluorinating Reagent for Enantioselective Fluorination2011

    • Author(s)
      Hiroyuki Yasui, Takeshi Yamamoto, Takehisa Ishimaru, Takeo Fukuzumi, Etsuko Tokunaga, Kakehi Akikazu, Mo too Shire, Norio Shibata
    • Journal Title

      J. Fluorine Chem

      Volume: 132(3) Pages: 222-225

    • Peer Reviewed
  • [Journal Article] Catalyst-Free and Catalytic Friedel Crafts Alkylations of Indoles in Solkane(R) 365mfc, an Environmentally Benign Alternative Solvent2011

    • Author(s)
      Xiu-Hua Xu, Akihiro Kusuda, Etsuko Tokunaga and Norio Shibata
    • Journal Title

      Green Chem

      Volume: 13 Pages: 46-50

    • Peer Reviewed
  • [Journal Article] Organic Reaction in Solkane(R) 365mfc : Homocoupling Reaction of Terminal Alkynes2011

    • Author(s)
      Akihiro Kusuda, Xiu-Hua Xu, Xin Wang, Etsuko Tokunaga and Norio Shibata
    • Journal Title

      Green Chem

      Volume: 13 Pages: 843-846

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Both Mirror Images of s' Fluorothalidomideby Enantiodivergent Fluorination Using a Single2011

    • Author(s)
      Takeshi Yamamoto, Yuka Suzuki, Emi Ita, Etsuko Tokunaga, and Norio Shibata
    • Journal Title

      Org. Lef

      Volume: 13(3) Pages: 470-473

    • Peer Reviewed
  • [Journal Article] Inherent Oxygen Preference in Enolate Monofluoromethylation and a Synthetic Entry to Monofluoromethyl Ethers2011

    • Author(s)
      Yoshinori Nomura, Etsuko Tokunaga, Prof. Norio Shibata
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 1885-1889

    • Peer Reviewed
  • [Journal Article] A sterically Demanding Electrophilic Fluorinating Reagent for Enantioselective Fluorination2011

    • Author(s)
      Hiroyuki Yasui, Takeshi Yamamoto, Takehisa Ishimaru, Takeo Fukuzumi, Etsuko Tokunaga, Kakehi Akikazu, Mo too Shire, Norio Shibata
    • Journal Title

      J. Fluorine Chem.

      Volume: 132(3) Pages: 222-225

    • Peer Reviewed
  • [Journal Article] Robust Synthesis of Trifluoromethionine and Its Derivatives by Reductive Trifluoromethylation of Amino Acid Disulfides by CFsI/Na/Liq. NH3 system2011

    • Author(s)
      Hiroyuki Yasui, Takeshi Yamamoto, Etsuko Tokunaga, Norio Shibata
    • Journal Title

      J. Fluorine Chem.

      Volume: 132(3) Pages: 186-189

    • Peer Reviewed
  • [Journal Article] Catalyst-Free and Catalytic Frieder-Crafts Alkylations of Indoles in Solkane(R) 365mfc, an Environmentally Benign Alternative Solvent2011

    • Author(s)
      Xiu-Hua Xu, Akihiro Kusuda, Etsuko Tokunaga, Norio Shibata
    • Journal Title

      Green Chem.

      Volume: 13 Pages: 46-50

    • Peer Reviewed
  • [Journal Article] Inherent Oxygen Preference in Enolate Monofluorome thylation and a Synthetic Entry to Monofluoromethyl Ethers2011

    • Author(s)
      Yoshinori Nomura, Etsuko Tokunaga, Norio Shibata
    • Journal Title

      Angew Chem. Int. Ed.

      Volume: 50 Pages: 1885-1889

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Both Mirror Images of s' Fluorothalidomide by Enantiodivergent Fluorination Using a Single2010

    • Author(s)
      Takeshi Yamamoto, Yuka Suzuki, Emi Ita, Etsuko Tokunaga, Norio Shibata
    • Journal Title

      Org. Left.

      Volume: 12(22) Pages: 5104-5107

    • Peer Reviewed
  • [Journal Article] Cinchona Alkaloid Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane2010

    • Author(s)
      Hiroyuki Kawai, Kentaro Tachi, Etsuko Tokunaga, Mo too Shire, Norio Shibata
    • Journal Title

      Org. Left.

      Volume: 12(22) Pages: 5104-5107

    • Peer Reviewed
  • [Journal Article] Expeditious Synthesis of Trifluoromethylated Heterocycles : Noncatalytic 1, sDipolar Cyclization of Azomethine Imines with(aTrifluoromethyl) acrylates2010

    • Author(s)
      Shinichi Ogawa, Takayuki Nishimine, Etsuko Tokunaga, Norio Shibata
    • Journal Title

      Synthesis

      Volume: 19 Pages: 3274-3281

    • Peer Reviewed
  • [Journal Article] Enantioselective Syntehsis of Trifluoromethyl Substituted 2 Isoxazolines : Asymmetric Hydroxylamine/Enone Cascade Reaction2010

    • Author(s)
      Kazutaka Matoba, Hiroyuki Kawai, Tatsuya Furukawa, Akihiro Kusuda, Etsuko Tokunaga, Shuichi Nakamura, Mo too Shire, Norio Shibata
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 49(33) Pages: 5762-5766

    • Peer Reviewed
  • [Journal Article] Trifluoroethoxy Coating Improves the Axal Ligand Substitution of Subphthalocyanine2010

    • Author(s)
      Norio Shibata, Banibrata Das, Etsuko Tokunaga, Mo too Shire, Nagao Kobayashi
    • Journal Title

      Chem. Eur : J

      Volume: 16(25) Pages: 7554-7562

    • Peer Reviewed
  • [Journal Article] Chinchona alkaloid/Ti' vCatalyzed Enantioselective Enamine Trifluoropyruvate Condensation Cyclization Reaction anc Its Application to Drug-like Heterocycles2010

    • Author(s)
      Shinichi Ogawa, Norihito Iida, Etsuko Tokunaga, Mo too Shire, Norio Shibata
    • Journal Title

      Chem. Eur J

      Volume: 16(24) Pages: 7090-7095

    • Peer Reviewed
  • [Journal Article] Perfluoroisopropyl Zinc Phthalocyaines Conjugated with Deoxyribonucleosides : Synthesis, Photophysical Properties and In Vitro PHotodynamic Activities2010

    • Author(s)
      Banibrata Das, Etsuko Tokunaga, Motohiro Tanaka, Takuma Sasaki, Norio Shibata
    • Journal Title

      Eur J. Org. Chem

      Volume: 15 Pages: 2878-2884

    • Peer Reviewed
  • [Journal Article] Solubility of Trifluoroethoxyphthalocyanines and Subphthalocyanines in Liquid and Supercritical Carbon Dioxide2010

    • Author(s)
      Banibrata Das, Etsuko Tokunaga, Norio Shibata, Nagao Kobayashi
    • Journal Title

      J. Fluorine Chem

      Volume: 131(5) Pages: 652-654

    • Peer Reviewed
  • [Journal Article] Enantioselective Frieder-Crafts Reaction of lsTrifluoromethylated Acrylates with Pyrroles and Its Application to the Synthesis of Trifluorinated Heliotridane2010

    • Author(s)
      Yiyong Hwang, Etsuko Tokunaga, Satoru Suzuki, Mo too Shire, Norio Shibata
    • Journal Title

      Org. Left

      Volume: 12(5) Pages: 1136-1138

    • Peer Reviewed
  • [Journal Article] Synthesis of Benzenecentered Trinuclear Phthalocyanines by Triple-click Chemistry2010

    • Author(s)
      Banibrata Das, Masashi Umeda, Etsuko Tokunaga, Takeshi Torn, Norio Shibata
    • Journal Title

      Chem. Left

      Volume: 39(4) Pages: 337-338

    • Peer Reviewed
  • [Journal Article] Self Disproportionation of Enantiomers of Heterocyclic Compounds Having a Tertiary Trifluoromethyl Alcohol Center on Chromatography with a Non Chiral System2010

    • Author(s)
      Shinichi Ogawa, Takayuki Nishimine, Etsuko Tokunaga, Shuichi Nakamura Norio Shibata
    • Journal Title

      J Fluorine Chem

      Volume: 131(4) Pages: 521-524

    • Peer Reviewed
  • [Journal Article] 2-Fluoro-1, 3-benzodithiole-1, 1, 3, 3-tetraoxide : A Reagent for Nucleophilic Monofluoromethylation of Aldehydes2010

    • Author(s)
      Tatsuya Furukawa, Yosuke Goto, Jumper Kawazoe, Etsuko Tokunaga, Shuichi Nakamura, Yudong Yang, Hongguang Du, Akikazu Kakehi, Mo too Shire, Norio Shibata
    • Journal Title

      Angew. Chem. Mt. Ed

      Volume: 49(9) Pages: 1642-1647

    • Peer Reviewed
  • [Journal Article] Efficient Access to Extended Yagupolskii Umemoto-Type Reagents : Triflic Acid Catalyzed Intramolecular Cyclization of or the Ethynylaryltrifluoromethylsulfanes2010

    • Author(s)
      Andrej Matsnev, Shun Noritake, Yoshinori Nomura, Etsuko Tokunaga, Shuichi Nakamura, Norio Shibata
    • Journal Title

      Angew. Chem. Mt. Ed

      Volume: 49(3) Pages: 572-576

    • Peer Reviewed
  • [Journal Article] Synthesis of Fluorinated Alienes via Palladium Catalyzed Monofluoromethylation Using FBSM2009

    • Author(s)
      Masamichi Ogasawara, HidetoshiMurakami, Tatsuya Furukawa, Tamotsu Takahashi, Norio Shibata
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 7366-7368

    • Peer Reviewed
  • [Journal Article] Construction of Nonadjacent Stereocenters Containing a Trifluoromethylated Carbon by Organocatalyzed Michael Addition of lsKetoesters to 2(Trifluoromethyl) acrylate2009

    • Author(s)
      Shinichi Ogawa, Hiroyuki Yasui, Shuichi Nakamura, Norio Shibata
    • Journal Title

      Chem. Left

      Volume: 10 Pages: 1006-1007

    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Thalidomide Deoxyribonucleoside Chimeras2009

    • Author(s)
      Shigeru Suzuki, Takeshi Yamamoto, Etsuko Tokunata, Shuichi Nakamura, Motohiro Tanaka, Takuma Sasaki, Norio Shibata
    • Journal Title

      Chem. Lef

      Volume: 11 Pages: 1046-1047

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of a Sulfenyl(sketoesters Using DBFOXPh/Ni(II) complex2009

    • Author(s)
      Takehisa Ishimaru, Shinichi Ogawa, Etsuko Tokunaga, Shuichi Nakamura, Norio Shibata
    • Journal Title

      J. Fluorine Chem

      Volume: 130(11) Pages: 1049-1053

    • Peer Reviewed
  • [Journal Article] Solkane(R) 365mfc is an Environmentally Benign Alternative Solvent for Trifluoromethylation Reaction2009

    • Author(s)
      Akihiro Kusuda, Hiroyuki Kawai, Shuichi Nakamura, Norio Shibata
    • Journal Title

      Green Chem

      Volume: 11 Pages: 1733-1735

    • Peer Reviewed
  • [Journal Article] Catalytic Enantioselective Trifluoro methylation of Azomethine Imines With Trimethyl(trifluoromethyl)2009

    • Author(s)
      Hiroyuki Kawai, Akihiro Kusuda, Shuichi Nakamura, Mo too Shire, Norio Shibata
    • Journal Title

      Angew. Chem. Mt. Ed

      Volume: 48(34) Pages: 6324-6327

    • Peer Reviewed
  • [Journal Article] Photophysical and Electrochemical Properties of Perfluoroisopropyl Substituted Binuclear Phthalocyanine Conjugated with a Butadiyne Linker2009

    • Author(s)
      Norio Shibata, Banibrata Das, Masamichi Hayashi, Shuichi Nakamura, Takeshi Torn
    • Journal Title

      J. Fluorine Chem

      Volume: 130(12) Pages: 1164-1170

    • Peer Reviewed
  • [Journal Article] A DBFOXPh-Based Combinatorial Catalyst for Enantioselective Fluorination of Aryl Acetyl and sButenoyl Thiazolidinones2009

    • Author(s)
      hande Sudhakar Reddy, Norio Shibata, Takao Horikawa, Satoru Suzuki, Shuichi Nakamura, Takeshi Torn, Mo too Shire
    • Journal Title

      Chemistry An Asian Journal

      Volume: 4(9) Pages: 1411-1415

    • Peer Reviewed
  • [Journal Article] Synthesis of Novel C2Symmetric Chiral Crown Ethers and Their Applications to Enantioselective Trifluoromethylation of Aldehydes and Ketones2009

    • Author(s)
      Hiroyuki Kawai, Akihiro Kusuda, ShuichiNakamura, Satoshi Mizuta, Yasuhiro Funahashi, Hideki Masuda, Norio Shibata
    • Journal Title

      J. Fluorine Chem

      Volume: 130(8) Pages: 762-765

    • Peer Reviewed
  • [Journal Article] Enantioselective Electrophilic Trifluoro methylation of ls-Keto Esters with Umemoto Reagents Induced by Chiral Nonracemic Guanidine2009

    • Author(s)
      Shun Noritake, Norio Shibata, Yoshinori Nomura, Yiyong Hwang, Andrej Matsnev, Shuichi Nakamura, Takeshi Toni, Dominique Canard
    • Journal Title

      Org. Biomol. Chem

      Volume: 7 Pages: 3599-3604

    • Peer Reviewed
  • [Journal Article] Ionic Liquids as Media for Nucleophilic Ring Opening Fluorination of Aziridines2009

    • Author(s)
      Shun Noritake, Norio Shibata, Hiroyuki Kawai, Pandy Manoj Kumar, Shuichi Nakamura, Takeshi Torn
    • Journal Title

      Heterocycl. Commun

      Volume: 15(2) Pages: 105-113

    • Peer Reviewed
  • [Journal Article] Synthesis of Trifluoroethoxy Coated Binuclear Phthalocyanines with Click Spacers and Investigation of Their Clamshell2009

    • Author(s)
      Behaviour, Yoshiyama, Norio Shibata, Takefumi Sate, Shuichi Nakamura, Takeshi Toru
    • Journal Title

      Org. Biomol. Chem

      Volume: 7(11) Pages: 2265-2269

    • Peer Reviewed
  • [Presentation] Asymmetric Allylic Fluoroalkylation of Morita BaylisHillman Adducts Catalyzed by Cinchona Alkaloid2011

    • Author(s)
      Takayuki Nishimine, Tatsuya Furukawa, Jumper Kawazoe, Wet Zhang, Etsuko Tokunaga, Norio Shibata
    • Organizer
      International Symposium on Catalysis and Fine Chemicals
    • Place of Presentation
      Nara, Japan
    • Year and Date
      20111204-08
  • [Presentation] Palladiumcatalyzed Decarboxylative Allylation of uTrifluoromethyl R-Keto Esters2011

    • Author(s)
      Satoru Suzuki, Etsuko Tokunaga, Norio Shibata
    • Organizer
      International Symposium on Catalysis and Fine Chemicals
    • Place of Presentation
      Nara, Japan
    • Year and Date
      20111204-08

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Published: 2013-07-31  

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