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Characterization and application of hydrophobic functionalities bearing heavier group 14 atoms

Research Project

Project/Area Number 23790128
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Drug development chemistry
Research InstitutionTokyo Medical and Dental University

Principal Investigator

FUJII Shinya  東京医科歯科大学, 生体材料工学研究所, 助教 (60389179)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords医薬品化学 / 疎水性相互作用 / 有機元素化学 / エストロゲン / 定量的構造活性相関 / 疎水性 / ケイ素 / ゲルマニウム / 分配係数 / 構造活性相関
Research Abstract

Systematic synthesis and characterization of simple phenols bearing a trialkyl(aryl)silyl or trialkyl(aryl)germyl functional group as a hydrophobic substituent were investigated. These silicon and germanium analogs exhibited higher hydrophobicity than the corresponding carbon analogs, with a difference in logP value of approximately 0.6, independent of the alkyl(aryl) species. The trialkylsilyl- and trialkylgermylphenols exhibited more potent estrogenic activity as compared with the carbon analogs. The substituent parameters and structure-activity relationship may be helpful for drug discovery utilizing the heavier group 14 elements.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (51 results)

All 2013 2012 2011 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (39 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 1 results)

  • [Journal Article] Increased Hydrophobicity and Estrogenic Activity of Simple Phenols with Silicon and Germanium- Containing Substituents2013

    • Author(s)
      Fujii, S.
    • Journal Title

      J. Med. Chem.

      Volume: 56 Issue: 1 Pages: 160-166

    • DOI

      10.1021/jm3013757

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Development of Androgen Recby Application of Ten-vertex p-Carborane as a Novel Hydrophobic Core Structure2012

    • Author(s)
      Shinya Fujii, Kiminori Ohta, Tokuhito Goto, Akifumi Oda, Hiroyuki Masuno, Ysuyuki Endo, Hiroyuki Kagechika
    • Journal Title

      Med. Chem. Commun

      Volume: 3 Issue: 6 Pages: 680-684

    • DOI

      10.1039/c2md00294a

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure-Comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives2012

    • Author(s)
      Wongmayura, A.
    • Journal Title

      Bioorg.Med Chem.Lett.

      Volume: 22 Issue: 4 Pages: 1756-1760

    • DOI

      10.1016/j.bmcl.2011.12.137

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Boron Cluster-based DevNon-Secosteroidal Vitamin D Receptor Ligands: Direct Observation of Hydrophobic Interaction between Protein Surface and Carborane2011

    • Author(s)
      Shinya Fujii, Hiroyuki Masuno, Yoshiyuki Taoda, Atsushi Kano, Angsuma Wongmayura, Makoto Nakabayashi, Nobutoshi Ito, Masato Shimizu, Emiko Kawachi, Tomoya Hirano, YasuyukiEndo, Aya Tanatani, Hiroyuki Kagechika
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Issue: 51 Pages: 20933-20941

    • DOI

      10.1021/ja208797n

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] p-Carborane Based AndrogenActive in LNCaP Cells with a Mutated Androgen Receptor2011

    • Author(s)
      Shinya Fujii, Ayumi Yamada, Keiko Tomita, Mao Nagano, Tokuhito Goto, Kiminori Ohta, Takashi Harayama, Yasuyuki Endo, Hiroyuki Kagechika
    • Journal Title

      Med. Chem. Commun

      Volume: 2 Issue: 9 Pages: 877-880

    • DOI

      10.1039/c1md00001b

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Efficient and diversity-oriented total synthesis of Riccardin C and application to develop novel macrolactam derivatives2011

    • Author(s)
      Iwashita, M.
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 33 Pages: 6073-6082

    • DOI

      10.1016/j.tet.2011.06.018

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Crystal Structure, Docking SStructure-activity Relationship of Carborane-containing Androgen2011

    • Author(s)
      Kiminori Ohta, Tokuhito Goto, Synya Fujii, Masatoshi Kawahata, Akifumi Oda, Shigeru Ohta, Kentaro Yamaguchi, Shuichi Hirono,Yasuyuki Endo
    • Journal Title

      Bioorg. Med. Chem

      Volume: 19 Issue: 11 Pages: 3540-3548

    • DOI

      10.1016/j.bmc.2011.04.017

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] 6-Arylcoumarins as novel nonsteroidal type progesterone antagonists : An example with receptor-binding-dependent fluorescence2011

    • Author(s)
      Sakai, H.
    • Journal Title

      J.Med.Chem.

      Volume: 54 Issue: 20 Pages: 7055-7065

    • DOI

      10.1021/jm2005404

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] シリル基・ゲルミル基の疎水性基としての性質と新規エストロゲン受容体リガンド創製への応用2013

    • Author(s)
      藤井晋也,宮島友,増野弘幸,影近弘之.
    • Organizer
      日本薬学会133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Final Research Report
  • [Presentation] シリル基・ゲルミル基の疎水性基としての性質と 新規エストロゲン受容体リガンド創製への応用2013

    • Author(s)
      藤井晋也
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] PRアンタゴニスト活性を有する新規ベンゼンスルホンアミド誘導体の創製2013

    • Author(s)
      山田歩
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] ビタミンK酸化誘導体の系統的合成とその生理活性2013

    • Author(s)
      清水章貴
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] カルボランを基盤とした新規VDRリガンドの構造活性相関2013

    • Author(s)
      藤原典子
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] 疎水性球状分子を骨格とする新規PRアンタゴニストの創製2013

    • Author(s)
      竹内由起
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] ピロールアミド誘導体の立体特性と環状トリアミドの創製2013

    • Author(s)
      武者祥昭
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] シリル基・ゲルミル基の疎水性基としての性質と新規エストロゲン受容体リガンドの創製2012

    • Author(s)
      藤井晋也,宮島友,増野弘幸,影近弘之.
    • Organizer
      日本レチノイド研究会第23回学術集会
    • Place of Presentation
      米子
    • Related Report
      2012 Final Research Report
  • [Presentation] Hydrophobic parameters, substituent constants and estrogenic activities of silyl- and germyl-containing phenols2012

    • Author(s)
      Fujii, S.; Miyajima, Y.; Masuno, H.; Kagechika, H.
    • Organizer
      ISMC2012 International Symposium of Medicinal Chemistry 2012
    • Place of Presentation
      ベルリン(ドイツ).
    • Related Report
      2012 Final Research Report
  • [Presentation] トリアルキルシリルおよびゲルミル基の性質と生理活性物質の疎水性構造への応用2012

    • Author(s)
      藤井晋也,宮島友,増野弘幸,影近弘之.
    • Organizer
      日本ケミカルバイオロジー研究会第7回年会
    • Place of Presentation
      京都
    • Related Report
      2012 Final Research Report
  • [Presentation] Development of Nuclear Receptor Ligands Based on Carborane as Hydrophobic Core Structure2012

    • Author(s)
      Fujii, S.; Yamada, A.; Ohta, K.; Endo, Y.; Kagechika, H.
    • Organizer
      The 1st HD Physiology International Symposium
    • Place of Presentation
      東京
    • Related Report
      2012 Final Research Report
  • [Presentation] Structure-activity relationship and structural basis of carborane-based VDR ligands2012

    • Author(s)
      Shinya Fujii
    • Organizer
      Molecular Chirality Asia 2012
    • Place of Presentation
      福岡
    • Related Report
      2012 Annual Research Report
  • [Presentation] Hydrophobic parameters, substituent constants and estrogenic activities of silyl- and germiyl-containing phenols2012

    • Author(s)
      Shinya Fujii
    • Organizer
      ISMC2012
    • Place of Presentation
      ベルリン(ドイツ)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Development of novel AR antagonists based on the structure of curcumin2012

    • Author(s)
      Ayumi Yamada
    • Organizer
      ISMC2013
    • Place of Presentation
      ベルリン(ドイツ)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of Novel VDR Ligand having A Spherical Hydrophobic Structure2012

    • Author(s)
      Hiroyuki Masuno
    • Organizer
      15th Vitamin D Workshop
    • Place of Presentation
      ヒューストン(アメリカ)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Development of Various Functional Molecules Based on Hydrophobic and Fluorescent Scaffolds2012

    • Author(s)
      Tomoya Hirano
    • Organizer
      ICBS2012
    • Place of Presentation
      ボストン(アメリカ)
    • Related Report
      2012 Annual Research Report
  • [Presentation] トリアルキルシリルおよびゲルミル基の性質と生理活性物質の疎水性構造への応用2012

    • Author(s)
      藤井晋也
    • Organizer
      ケミカルバイオロジー学会第7回年会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] トリアジン構造を基盤としたNFκB-DNA結合阻害剤の創製2012

    • Author(s)
      藤井晋也
    • Organizer
      ケミカルバイオロジー学会第7回年会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] カルボランを含有する共役大環状化合物の創製2012

    • Author(s)
      飯濱翔太郎
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] シリル基・ゲルミル基の疎水性基としての性質と新規エストロゲン受容体リガンドの創製2012

    • Author(s)
      藤井晋也
    • Organizer
      第23回日本レチノイド研究会学術集会
    • Place of Presentation
      米子
    • Related Report
      2012 Annual Research Report
  • [Presentation] Development of Nuclear Receptor Ligands Based on Carborane as Hydrophobic Core Structure.2012

    • Author(s)
      Shinya Fujii, Ayumi Yamada Kiminori Ohta, Yasuyuki Endo, Hiroyuki Kagechika
    • Organizer
      The 1st HD Physiology International Symposium
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Research-status Report
  • [Presentation] Development of Fluorescent Ligands for Nuclear Hormone Receptor.2012

    • Author(s)
      Tomoya Hirano, Haruka Sakai, Shuichi Mori, Shinya Fujii, Hiroyuki Masuno, Marie Kinoshita, Aya Tanatani, Hiroyuki Kagechika
    • Organizer
      The 1st HD Physiology International Symposium
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Research-status Report
  • [Presentation] クルクミンの構造要素を基盤とした新規ARアンタゴニストの創製2012

    • Author(s)
      山田 歩、藤井 晋也、影近 弘之
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2011 Research-status Report
  • [Presentation] トリアジン構造を基盤とした新規NF-κB阻害剤の創製2012

    • Author(s)
      中津 亜紀, 藤井 晋也, 小林 隆信, 宮澤 宏, 影近 弘之
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2011 Research-status Report
  • [Presentation] カルボランアニオンの炭素頂点におけるクロスカップリング反応の開発2012

    • Author(s)
      金澤 純一朗,滝田 良,藤井 晋也,影近 弘之,内山 真伸
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2011 Research-status Report
  • [Presentation] 球状の脂溶性ファーマコフォアを有するビタミンD誘導体の創製2012

    • Author(s)
      Angsuma WONGMAYURA,藤井 晋也,伊藤 茂,河内 恵美子,影近 弘之,棚谷 綾
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2011 Research-status Report
  • [Presentation] 変異アンドロゲン受容体(AR) にも有効な新規カルボラン含有AR アンタゴニストの創製2012

    • Author(s)
      皆瀬 麻子,後藤 徳仁,藤井 晋也,太田 公規,遠藤 泰之
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2011 Research-status Report
  • [Presentation] Development and structural basis of novel non-secosteroidal VDR ligands based on hydrophobic carborane cage2011

    • Author(s)
      Fujii, S.; Masuno, H.; Nakabayashi, M.; Hirano, T.; Kawachi, E.; Ito, N.; Kagechika, H.
    • Organizer
      IME Boron XIV 14th International Meeting on Boron Chemistry
    • Place of Presentation
      ナイアガラフォールズ(カナダ)
    • Related Report
      2012 Final Research Report
  • [Presentation] Development and structural basis of novel non-secosteroidal VDR ligands based on hydrophobic carborane cage.2011

    • Author(s)
      Fujii, S.; Masuno, H.; Nakabayashi, M.; Hirano, T.; Kawachi, E.; Ito, N.; Kagechika, H.
    • Organizer
      IME Boron XIV
    • Place of Presentation
      Niagara Falls, Canada
    • Related Report
      2011 Research-status Report
  • [Presentation] Development of novel carborane-based androgen receptor antagonists effective to mutated receptor.2011

    • Author(s)
      Yamada, A.; Fujii, S.; Tomita, K.; Nagano, M.; Harayama, T.; Ohta, K.; Endo, Y.; Kagechika, H.
    • Organizer
      IME Boron XIV
    • Place of Presentation
      Niagara Falls, Canada
    • Related Report
      2011 Research-status Report
  • [Presentation] Novel non-secosteroidal vitamin D receptor ligands bearing a spherical hydrophobic core. - Difference between carborane and bicyclohydrocarbon -2011

    • Author(s)
      Angsuma, W.; Fujii, S.; Sekine, R.; Kano, A.; Kawachi, E.; Masuno, H.; Hirano, T.; Kagechika, H.; Tanatani, A.
    • Organizer
      IME Boron XIV
    • Place of Presentation
      Niagara Falls, Canada
    • Related Report
      2011 Research-status Report
  • [Presentation] Design and synthesis of novel AR antagonists having a grycerol moiety.2011

    • Author(s)
      Kaise, A.; Goto, T.; Fujii, S.; Ohta, K.; Endo, Y.
    • Organizer
      IME Boron XIV
    • Place of Presentation
      Niagara Falls, Canada
    • Related Report
      2011 Research-status Report
  • [Presentation] Efficient and Diversity-Oriented Total Synthesis of Riccardin C.2011

    • Author(s)
      Shinya Fujii, Masazumi Iwashita, Shigeru Ito, Tomoya Hirano, Hiroyuki Kagechika
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Research-status Report
  • [Presentation] Development of Novel Progesterone Receptor Antagonists Based on Boron Cluster as a Hydrophobic Core Structure2011

    • Author(s)
      Eiichi Nakano, Naoki Yanagida, Shuichi Mori, Shinya Fujii, Hiroyuki Kagechika
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Research-status Report
  • [Presentation] Development of Silicon- and Germanium-containing Ligands for Nuclear Receptors.2011

    • Author(s)
      Masuno, H., Fujii, S., Miyajima, Y., Kawachi, E., Kagechika, H.
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Research-status Report
  • [Presentation] Development of Novel AR Antagonists Active in LNCaP Cells with Mutated Androgen Receptor.2011

    • Author(s)
      Yamada, A., Fujii, F., Tomita, K., Nagano, M., Harayama, T., Ohta, K., Endo, Y., Kagechika, H.
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Research-status Report
  • [Presentation] Design and synthesis of novel carborane-containing AR antagonists having a grycerol moiety based on the co-crystal structure of bicalutamide with hAR LBD.2011

    • Author(s)
      Kaise, A., Goto, T., Fujii, S., Ohta, K., Endo, Y.
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Research-status Report
  • [Presentation] ケイ素およびゲルマニウムを持つレチノイドX受容体リガンドの開発2011

    • Author(s)
      増野弘幸,藤井晋也,前田満将,前田貴志,平野智也,河内恵美子,影近弘之
    • Organizer
      日本ビタミン学会第63回大会
    • Place of Presentation
      広島
    • Related Report
      2011 Research-status Report
  • [Presentation] N,N’-ジアリールスクアルアミドの立体特性2011

    • Author(s)
      神田翠,藤井晋也,片桐幸輔,桝飛雄真,東屋功,影近弘之,棚谷綾.
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://www.tmd.ac.jp/mri/omc/index1.html

    • Related Report
      2012 Final Research Report
  • [Remarks] 薬化学分野 - 東京医科歯科大学

    • URL

      http://www.tmd.ac.jp/mri/omc/index1.html

    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 新規アンドロゲン受容体アンタゴニスト2013

    • Inventor(s)
      影近弘之、藤井晋也、山田歩
    • Industrial Property Rights Holder
      影近弘之、藤井晋也、山田歩
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-02-28
    • Related Report
      2012 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 新規アンドロゲン受容体アンタゴニスト2012

    • Inventor(s)
      影近弘之、藤井晋也、山田歩
    • Industrial Property Rights Holder
      東京医科歯科大学
    • Industrial Property Number
      2012-043959
    • Filing Date
      2012
    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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