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Research for the function of nuclear receptors using 9Z-retinoic acid analogs

Research Project

Project/Area Number 12672165
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 医薬分子機能学
Research InstitutionKobe Pharmaceutical University

Principal Investigator

ITO Masayoshi  Kobe Pharm Univ., Professor, 薬学部, 教授 (20068331)

Co-Investigator(Kenkyū-buntansha) WADA Akimori  Kobe Pharm Univ., Associate Professor, 薬学部, 助教授 (80158683)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2002: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2001: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2000: ¥1,400,000 (Direct Cost: ¥1,400,000)
Keywordsretinoic acid analog / nuclear receptor / RXR / RAR / Stereoselective synthesis / coupling reaction / stannyl olefin / enol triflate / ノナフレート / 9cis-レチノイン酸アナログ / パラジウム触媒 / ビニルトリフレート
Research Abstract

Stereoselective synthesis of di- and tri-substituted olefins was investigated.
A Palladium catalyzed cross coupling reactions of vinyl triflate and Z-alkenyl stannanes afforded stereoselectively the trisubstituted Z-olefins in high yields, which were converted to the corresponding 9Z-retinoic acids via Emmons-Horner reaction and subsequent basic hydrolysis in excellent yields.
On the contrary, a palladium catalyzed cross coupling reactions of E-tetraenyl stannanes, derived from the terminal acetylenes, with E- or Z-vinyl triflates afforded the novel method for the stereoselective synthesis of all-E-, 13Z- and 9Z- retinoic acid esters in good yields. Applying this methodology, 13-substituted all-E- and 9Z- retinoic acids were prepared in satisfactory yields.
Now, the structural and biological activity relationship of these analogs is in progress.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] A.Wada: "A Higly Stereoselective Synthesis of 11Z-retinal Using Tricarbony Iron Complex and Acetylenes"I.Org.Chem. 69(8). 2438-2443 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A.Wada: "Synthesis of 9Z-9-Substituted Retinoic Acids by Palladium Catalyzed Coupling Reaction of a Vinyl Triflate with Alkenyl Stannanes"Chem.Pharma.Bull.. 48(9). 1391-1394 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A.Wada: "Synthesis of 11Z-9-Demethyl-9-((3-indolyl)methyl)retinal"J.Heterocyclic Chem.. 38. 259-264 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A.Wada: "Stereocontrolled Synthesis of 13-Substituted Retinoic Acids by Palladium-Catalyzed Coupling Reaction of Alkenyl Stannane with Vinyl Triflate"Synlett. 800-802 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A.Wada: "Synthesis of all-E-and 9Z-Heteroaryl-retinoic Acid Applying Palladium Catalyzed Coupling Reaction"Synlett. 1759-1762 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A.Wada: "Palladium Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes"Synlett. 1061-1064 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A. Wada, N. Fujioka, Y. Tanaka, M. Ito: "A Highly Stereoselective Synthesis of 11Z-retinal Using Tricarbonyl Iron Complex"J. Org. Chem.. 65(8). 2438-2443 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A. Wada, Y. Nomoto, K. Tano, E. Yamashita, M. Ito: "Synthesis of 9Z-9-Substituted Retinoic Acids by Palladium Catalyzed Coupling Reaction of a Vinyl Triflate with Alkenyl Stannanes"Chem. Pharma. Bull. 48(9). 1391-1394 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A. Wada, N. Fujioka, M. Ito: "Synthesis of 11Z-9-Demethyl-9-((3-indolyl)methyl)retinal"J. Heterocyclic Chem.. 38. 259-264 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A. Wada, K. Fukunaga, M. Ito: "Stereocontrolled Synthesis of 13-Substituted Retinoic Acids by Palladium-Catalyzed Coupling Reaction of Alkenyl Stannane with Vinyl Triflate"Synlett. 800-802 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A. Wada, G. Babu, S. Shimomoto, M. Ito: "Synthesis of all-E- and 9Z-Heteroaryl-retinoic Acid Applying Palladium Catalyzed Coupling Reaction of (Arylvinyl)tributyl-stannane with Vinyl Triflate"Synlett. 1759-1762 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A. Wada, Y. Ieki, M. Ito: "Palladium Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes"Synlett. 1061-1064 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A.Wada: "Palladium Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes"Synlett. 1061-1064 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] A.Wada: "Synthesis of 11Z-9-Demethyl-9-((3-indolyl)methyl)retinal"J. Heterocyclic Chem.. 38(1). 259-264 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] A.Wada: "Stereocontrolled Synthesis of 13-Substituted Retinoic Acids by Palladium-Catalyzed Coupling Reaction of Alkenyl Stannane with Vinyl Triflate"Synlett. (5). 800-802 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] A.Wada: "Synthesis of all-E-and 9Z-Heteroaryl-retinoic Acid Applying Palladium Catalyzed Coupling Reaction of (Arylvinyl)tributylstannane with Vinyl Triflate"Synlett. (11). 1759-1762 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] A.Wada,: "A Higly Stereoselective Synthesis of 11Z-retinal Using Tricarbonyl Iron Complex"J.Org.Chem.,. 65(8),. 2438-2443 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Wada,: "Synthesis of 9Z-9-Substituted Retinoic Acids by Palladium Catalyzed Coupling Reaction of a Vinyl Triflate with Alkenyl Stannanes"Chem.Pharma.Bull.,. 48(9),. 1391-1394 (2000)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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