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Research of retinoic acid-modified nuclear receptor agonist

Research Project

Project/Area Number 20790105
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Drug development chemistry
Research InstitutionKobe Pharmaceutical University

Principal Investigator

OKITSU Takashi  Kobe Pharmaceutical University, 薬学部, 助教 (50441209)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2009: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2008: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Keywords医薬分子設計 / 核内受容体 / レチノイド / RXR / RAR / テルペノイド / メタボリック症候群 / 癌 / Stilleカップリング / Stileカップリング
Research Abstract

The ligand molecules of retinoid X receptors (RXRs) are candidates for therapeutic agents of metabolic syndrome such as dyslipidemia and type II diabete. The natural ligand of RXR is 9Z-retinoic acid so that I have developed an efficient synthesis of 9Z-rerinoic acid and its analogs. Among them, (-)-menthol congener had strong RXRα agonist activity. It is noteworthy that an analog having indole showed isotype selectivity (RXRα>γ). In the process of my project, I also discovered novel iodocyclizations leading to benzofurans and spiro compounds.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (47 results)

All 2010 2009 2008 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (30 results) Remarks (3 results)

  • [Journal Article] Synthesis and biological evaluation of 9Z-retinoic acid analogs having 2-substituted benzo[b]furan2010

    • Author(s)
      Okitsu, T.; Nakazawa, D.; Nakagawa, K.; Okano, T.; Wada, A.
    • Journal Title

      Chem. Pharm. Bull. 58

      Pages: 418-422

    • NAID

      130000255927

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] ipso-Iodocyclization of ethoxyethyl ethers to alkynes at the ortho-position: an efficient synthesis of functionalized spiro compounds2010

    • Author(s)
      Okitsu, T.; Nakazawa, D.; Kobayashi, A.; Mizohata, M.; In, Y.; Ishida, T.; Wada, A.
    • Journal Title

      Synlett

      Pages: 203-206

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] ipso-Iodocyclization of ethoxyethyl ethers to alkynes at the ortho-position : an efficient synthesis of functionalized spiro compounds2010

    • Author(s)
      Okitsu, T., Nakazawa, D., Kobayashi, A., Mizohata, M., In, Y., Ishida, T., Wada, A.
    • Journal Title

      Synlett

      Pages: 203-206

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and biological evaluation of 9Z-retinoic acid analogs having 2-substituted benzo[b]furan2010

    • Author(s)
      Okitsu, T., Nakazawa, D., Nakagawa, K., Okano, T., Wada, A.
    • Journal Title

      Chem.Pharm.Bull. 58

      Pages: 418-422

    • NAID

      130000255927

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organic chemistry using weakly electrophilic salts: the reaction with nitrogen nucleophiles2009

    • Author(s)
      Fujioka, H.; Kubo, O.; Senami, K.; Okamoto, K.; Okitsu, T.; Kita, Y.
    • Journal Title

      Heterocycles 79

      Pages: 1113-1120

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Mild and efficient deprotection of acetal-type protecting groups of hydroxyl functions by triethylsilyl triflate-2, 4, 6-collidine combination2009

    • Author(s)
      Fujioka, H.; Kubo, O.; Okamoto, K.; Senami, K.; Okitsu, T.; Ohnaka, T.; Sawama, Y.; Kita, Y.
    • Journal Title

      Heterocycles 77

      Pages: 1089-1103

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Mild and efficient deprotection of acetal-type protecting groups of hydroxyl functions by triethylsilyl triflate-2, 4, 6-collidine combination2009

    • Author(s)
      Fujioka, H., Kubo, O., Okamoto, K., Senami, K., Okitsu, T., Ohnaka, T., Sawama, Y., Kita, Y.
    • Journal Title

      Heterocycles 77

      Pages: 1089-1103

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organic chemistry using weakly electrophilic salts : the reaction with nitrogen nucleophiles2009

    • Author(s)
      Fujioka, H., Kubo, O., Senami, K., Okamoto, K., Okitsu, T., Kita, Y.
    • Journal Title

      Heterocycles 79

      Pages: 1113-1120

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Steric constraint in the primary photoproduct of sensory rhodopsin II is a prerequisite for light-signal transfer to HtrII2008

    • Author(s)
      Ito, M.; Sudo, Y.; Furutani, Y.; Okitsu, T.; Wada, A.; Homma, M.; Spudich, J.L.; Kandori, H.
    • Journal Title

      Biochemistry 47

      Pages: 6208-6215

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Caesium fluoride-promoted Stille coupling reaction: An efficient synthesis of 9Z-retinoic acid and its analogues using a practical building block2008

    • Author(s)
      Okitsu, T.; Iwatsuka, K.; Wada, A.
    • Journal Title

      Chem. Commun.

      Pages: 6330-6332

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iodocyclization of ethoxyethyl ethers to alkynes: A broadly applicable synthesis of 3-iodobenzo[b]furans2008

    • Author(s)
      Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A.
    • Journal Title

      Org. Lett. 10

      Pages: 4967-4970

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Caesium fluoride-promoted Stifle coupling reaction : An efficient synthesis of 9Z-retinoic acid and its analogues using a practical building block2008

    • Author(s)
      Okitsu, T.; Iwatsuka, K.; Wada, A.
    • Journal Title

      Chem. Commun

      Pages: 6330-6332

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iodocyclization of ethoxyethyl ethers to alkynes : A broadly applicable synthesis of 3-iodobenzo [b]furans2008

    • Author(s)
      Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A.
    • Journal Title

      Org. Lett 10

      Pages: 4967-4970

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Steric constraint in the primary photoproduct of sensory rhodopsin II is a prerequisite for light-signal transfer to HtrII2008

    • Author(s)
      Ito, M.; Sudo, Y.; Furutani, Y.; Okitsu, T.; Wada, A.; Homma, M.; Spudich, J. L.; Kandori, H.
    • Journal Title

      Biochemistry 47

      Pages: 6208-6215

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] ヒドラジドを求核種とするヨード環化反応の開発2010

    • Author(s)
      沖津貴志, 佐藤可奈, 和田昭盛
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] アルコキシアミン類を求核種とするヨード環化反応の開発2010

    • Author(s)
      沖津貴志, Potewar, TM., 佐藤可奈, 和田昭盛
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] 9Z-レチノイン酸及び誘導体の高効率的合成と転写活性2009

    • Author(s)
      沖津貴志, 岩塚欣也, 澤田夏美, 中川公恵, 岡野登志夫, 和田昭盛
    • Organizer
      第28回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2009-11-25
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] テルペノイド由来疎水性ユニットを組み込んだ9Z-レチノイン酸の合成と転写活性2009

    • Author(s)
      沖津貴志, 佐藤可奈, 澤田夏美, 中川公恵, 岡野登志夫, 和田昭盛
    • Organizer
      第28回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2009-11-25
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] ヨード環化反応を利用したジヒドロピラゾール及びピラゾールの選択的合成2009

    • Author(s)
      沖津貴志, 佐藤可奈, 和田昭盛
    • Organizer
      第29回有機合成若手セミナー
    • Place of Presentation
      神戸
    • Year and Date
      2009-11-24
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] 9Z-レチノイン酸の効率的合成とその応用2009

    • Author(s)
      沖津貴志, 岩塚欣也, 和田昭盛, 中川公恵, 岡野登志夫
    • Organizer
      第20回日本レチノイド研究会
    • Place of Presentation
      東京
    • Year and Date
      2009-11-21
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] ヨウ素環化反応を機軸とするスピロ環の合成2009

    • Author(s)
      沖津貴志, 中澤大祐, 小林亮広, 溝畑雅裕, 和田昭盛
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-16
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] Concise Construction of 3-Iodobenzo[b]furans by Iodocyclization2009

    • Author(s)
      Okitsu, T.; Nakazawa, D.; Wada, A.
    • Organizer
      The Eleventh International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2009-11-10
    • Related Report
      2009 Final Research Report
  • [Presentation] Concise Construction of 3-Iodobenzo[b]furans by lodocyclization2009

    • Author(s)
      沖津貴志, 中澤大祐, 和田昭盛
    • Organizer
      The Eleventh International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2009-11-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] 重水素標識したゲラニルゲラニオールおよびビタミンKの合成2009

    • Author(s)
      和田昭盛, 須原義智, 山野由美子, 沖津貴志
    • Organizer
      第53回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      生駒
    • Year and Date
      2009-11-07
    • Related Report
      2009 Final Research Report
  • [Presentation] 重水素標織したゲラニルゲラニオールおよびビタミンKの合成2009

    • Author(s)
      和田昭盛, 須原義智, 山野由美子, 沖津貴志
    • Organizer
      第53回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      生駒
    • Year and Date
      2009-11-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] ヨウ素環化反応を用いるベンゾフラン類の網羅的合成2009

    • Author(s)
      沖津貴志, 中澤大祐, 和田昭盛
    • Organizer
      第59回日本薬学会近畿支部総会・大会
    • Place of Presentation
      東大阪
    • Year and Date
      2009-10-24
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] ヒドラジン誘導体を求核種とするヨウ素環化反応の開発2009

    • Author(s)
      沖津貴志, 佐藤可奈, 和田昭盛
    • Organizer
      第59回日本薬学会近畿支部総会・大会
    • Place of Presentation
      東大阪
    • Year and Date
      2009-10-24
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] ヨウ素環化反応を活用する多官能性スピロ複素環の合成2009

    • Author(s)
      沖津貴志, 中澤大祐, 小林亮広, 溝畑雅裕, 尹康子, 石田寿昌, 和田昭盛
    • Organizer
      第59回日本薬学会近畿支部総会・大会
    • Place of Presentation
      東大阪
    • Year and Date
      2009-10-24
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] Domino process of iodocyclization and Diels-Alder reaction for the construction of bridgehead-spiro heterocycles2009

    • Author(s)
      Okitsu, T.; Nakazawa, D.; Wada A.
    • Organizer
      22nd International Congress on Heterocyclic Chemistry
    • Place of Presentation
      St. John's
    • Year and Date
      2009-08-04
    • Related Report
      2009 Final Research Report
  • [Presentation] Domino process of iodocyclization and Diels-Alder reaction for the construction of bridgehead-spiro heterocycles2009

    • Author(s)
      沖津貴志, 中澤大祐, 和田昭盛
    • Organizer
      22nd International Congress on Heterocyclic Chemistry
    • Place of Presentation
      St.John's
    • Year and Date
      2009-08-04
    • Related Report
      2009 Annual Research Report
  • [Presentation] ヨウ素環化反応を利用する複素環合成2009

    • Author(s)
      沖津貴志, 中澤大祐, 小林亮広, 溝畑雅裕, 和田昭盛
    • Organizer
      第7回次世代を担う有機化学シンポジウム
    • Place of Presentation
      吹田
    • Year and Date
      2009-07-23
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] 環修飾レチノイン酸アナログの生物活性における置換基効果2009

    • Author(s)
      沖津貴志, 岩塚欣也, 中澤大祐, 和田昭盛, 中川公恵, 岡野登志夫
    • Organizer
      第324回脂溶性ビタミン総合研究委員会
    • Place of Presentation
      神戸
    • Year and Date
      2009-07-10
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] 9Z-レチノイン酸及び誘導体の高効率的合成と生物活性2009

    • Author(s)
      沖津貴志, 岩塚欣也, 中川公恵, 岡野登志夫, 和田昭盛
    • Organizer
      日本ビタミン学会第61回大会
    • Place of Presentation
      亀岡
    • Year and Date
      2009-05-31
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] 4-置換-2H-クロメン環を有するレチノイン酸類の合成と生物活性2009

    • Author(s)
      和田昭盛, 沖津貴志, 岩塚欣也, 中川公恵, 岡野登志夫
    • Organizer
      日本ビタミン学会第61回大会
    • Place of Presentation
      亀岡
    • Year and Date
      2009-05-31
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] ヨウ素環化反応による多官能性スピロ化合物の合成2009

    • Author(s)
      沖津貴志、中澤大祐、小林亮広、溝畑雅裕、尹康子、石田寿昌、和田昭盛
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] ヨウ素環化反応を用いた3-iodobenzo[b]furanの簡便構築法における置換基の効果2009

    • Author(s)
      中澤大祐、沖津貴志、松岡るみ、和田昭盛
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] ヨウ素環化反応による多官能性スピロ化合吻の合成2009

    • Author(s)
      沖津貴志、中澤大祐、小林亮広、溝畑雅裕、弄康子、石田寿昌、和田昭盛
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] 4-置換-2H-クロメン環を有するレチノイン酸類の合成と生物活性について2008

    • Author(s)
      和田昭盛、沖津貴志、岩塚欣也、中川公恵、岡野登志夫
    • Organizer
      日本レチノイド研究会第19回学術集会
    • Place of Presentation
      東京
    • Year and Date
      2008-11-22
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] ヨウ素環化反応を利用するベンゾフラン環の簡便構築法2008

    • Author(s)
      沖津貴志、中澤大祐、谷口理恵、和田昭盛
    • Organizer
      第34回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2008-11-04
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] 3-ヨードベンゾフランの新規合成法2008

    • Author(s)
      沖津貴志、中澤大祐、谷口理恵、和田昭盛
    • Organizer
      第58回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸
    • Year and Date
      2008-10-25
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] 9Z-レチノイン酸の効率的合成とアナログ合成への応用2008

    • Author(s)
      岩塚欣也、沖津貴志、和田昭盛
    • Organizer
      第50回天然有機化合物討論会
    • Place of Presentation
      博多
    • Year and Date
      2008-10-01
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] 9Z-レチノイン酸とその誘導体の効率的合成法2008

    • Author(s)
      岩塚欣也、沖津貴志、和田昭盛
    • Organizer
      第22回カロテノイド研究談話会
    • Place of Presentation
      沖縄
    • Year and Date
      2008-06-28
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] AN EFFICIENT SYNTHESIS OF 9Z-RETINOIC ACID AND ITS ANALOGUES USING A PRACTICAL BUILDING BLOCK2008

    • Author(s)
      Okitsu, T.; Iwatsuka, K.; Wada, A.
    • Organizer
      THE 15th INTERNATIONAL SYMPOSIUM ON CAROTENOIDS
    • Place of Presentation
      沖縄
    • Year and Date
      2008-06-25
    • Related Report
      2009 Final Research Report
  • [Presentation] AN EFFICIENT SYNTHESIS OF 9Z-RETINOIC ACID AND ITS ANALOGUES USING A PRACTICAL BUILDING BLOCK2008

    • Author(s)
      Okitsu, T.; Iwatsuka, K.; Wada, A.
    • Organizer
      THE 15^<th> INTERNATIONAL SYMPOSIUM ON CAROTENOIDS
    • Place of Presentation
      沖縄
    • Year and Date
      2008-06-25
    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.kobepharma-u.ac.jp/~ocls/index.html

    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://www.kobepharma-u.ac.jp/~ocls/index.html

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www.kobepharma-u.ac.jp/~ocls/index.html

    • Related Report
      2008 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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