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Study on Electronic and Steric Effects of Boron Cluster and Application for Construction of Functional Molecules.

Research Project

Project/Area Number 13470468
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTohoku Pharmaceutical University (2002-2003)
The University of Tokyo (2001)

Principal Investigator

ENDO Yasuyuki  Tohoku Pharmaceutical University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (80126002)

Co-Investigator(Kenkyū-buntansha) OHTA Kiminori  Tohoku Pharmaceutical Sciences, Faculty of Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (90347906)
INOMATA Kohei  Tohoku Pharmaceutical University, Faculty of Pharmaceutical Sciences, Lecturer, 薬学部, 講師 (60221785)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥14,200,000 (Direct Cost: ¥14,200,000)
Fiscal Year 2003: ¥4,300,000 (Direct Cost: ¥4,300,000)
Fiscal Year 2002: ¥4,500,000 (Direct Cost: ¥4,500,000)
Fiscal Year 2001: ¥5,400,000 (Direct Cost: ¥5,400,000)
Keywordscarborane / molecular construction / functional molecule / receptor / hydrophobic interaction / liquid crystal / drug design / 医薬分子設計 / 疎水性相互 / アセチレン / 加溶媒分解 / 反応速度解析 / 求核性 / 芳香族ウレア / 芳香族多層構造
Research Abstract

Carboranes (dicarba-closo-dodecaboranes) are a class of carbon-containing polyhedral boron-cluster compounds having globular shape, remarkable thermal stability and hydrophobic character. In this study, we applied their molecular shape and hydrophobic surface of the molecules to design and synthesis of functional molecules as follows.
1. Molecular construction of layered and cyclic molecules with carboranes and benzenes.
2. Design and synthesis of mesogenic molecules with carboranes instead of benzenes and cycloalkane.
3. Design and synthesis of carborane containing nuclear receptor ligands that interact hydrophobically with receptors.
The results achieved in this project (1 and 2) should make it possible to utilize construction of nano-scale chemistry and materials sciences. On the other hands, development of the potent carborane-containing nuclear receptor modulators (retinoid receptor ligands and estrogen receptor ligands) should yield novel candidate therapeutic agents, especially selective receptor modulators. Furthermore, the suitability of the spherical carborane cage for bindiiig to the cavity of receptor should provide a basis for a similar approach to developing novel ligands for other pharmaceutics

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (49 results)

All Other

All Publications (49 results)

  • [Publications] Yasuyuki Endo: "Potent Estrogen Agonists Based on Carborane as a Hydrophobic Skeletal Structure. A New Medicinal Application of Boron Clusters"Chem.Biol.. 8. 341-355 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuyuki Endo: "Medicinal Application of Dicarba-closo-dodecaboranes. Relation between Retinoidal Activity and Conformation of Two Aromatic Nuclei."BioMed.Chem.Lett.. 11. 1307-1311 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Sonei Sou: "α-Glucosidase Inhibitors with 4,5,6,7-Tetrachlorophtalimide Skeleton with a Cycloalkyl or Dicarba-closo-dodecaborane"Chem.Pharm.Bull.. 49. 791-793 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Chalermkiat Songkram: "Molecular Construction Based on Icosahedral Carboranes and Aromatic Urea Groups. A New Type of Carboracycles"Tetrahedron Lett.. 42. 5913-5916 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Keisuke Yamamoto: "Utility of Boron Clusters for Drug Design. Hansch-Fujita Hydrophobic Parameters π of Dicarba-closo-dodecaboranyl Groups"BioMed.Chem.Lett.. 11. 2389-2392 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuyuki Endo: "Electronic Effects of Icosahedral Carboranes : Kinetic Evidence for Interaction between Boron Atom and Nucleophile on the Solvolysis of (o-Carboranyl) benzyl Tosylates"Tetrahedron Lett.. 42. 6327-6331 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Chalermkiat Songkram: "Structures of Bis- and Tris(2-phenyl-o-carboran-1-yl)benzenes. Construction of Three-dimensional Structures Converted from Planar Arylacetylenic Arrays"Tetrahedron Lett.. 42. 6365-6368 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Tetsuya Toya: "Cyclic Dibenzoylhydrazines Reproducing the Conformation of Ecdyson Agonists, RH-5849. Importance of Hydrogen-bonding Character of NH Group"BioMed.Chem.. 10. 953-961 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuyuki Endo: "Molecular Construction Based on Icosahedral Carboranes and Aromatic N,N'-Dimethylurea Groups. Aromatic Layered Molecules"J.Organomet.Chem.. 657. 48-58 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Jayaseharan Johnsamuel: "A new strategy for molecular modeling and receptor-based design of carborane containing compounds"J.Organomet.Chem.. 680. 223-231 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Jayaseharan Johnsamuel: "A Convenient Method for the Computer-Aided Molecular Design of Carborane Containing Compounds"BioMed.Chem.Lett.. 13. 3213-3216 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuyuki Endo: "Boron clusters for medicinal drug design : Selective estrogen receptor modulators bearing carborane"Pure Appl.Chem.. 75. 1197-1205 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuyuki Endo: "Utility of Boron Clusters for Drug Design. Relation between Estrogen Receptor Binding Affinity and Hydrophobicity of Phenols Bearing Carboranyl Groups"BioMed.Chem.Lett.. 13. 4089-4092 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yoshiyuki Taoda: "Electronic Effects of Icosahedral Carboranes : Mechanistic Alteration in Solvolysis of a-(o-Carboranyl)benzyl Tosylates by Electronic Effect of Substituents"Tetrahedron Lett.. 44. 8177-8181 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kiminori Ohta: "Structural Effects in Three-Ring Mesogenic Derivatives of p-Carborane and Their Hydrocarbon Analogs"Liq.Cryst.. (印刷中). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuyuki Endo: "Boron Chemistry at the Beginning of the 21th Century"Bubnov, Yu., et al.(eds.) Russian Academy of Sciences, Nauka, Moscow. 298-306 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Detlef Gabel: "Molecular Clusters of the Main-Group Elements"Driess, M. ; Noth, H (eds.), Wiley-VHC, Weinheim (印刷中). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Endo, Y., Iijima, T., Yarnakoshi, Y., Fukasawa, H., Miyaura, C., Inada, M., Kubo, A., Itai, A.: "Potent Estrogen Agonists Based on Carborane as a Hydrophobic Skeletal Structure. A New Medicinal Application of Boron Clusters."Chem.Biol.. 8. 341-355 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Endo, Y., Iijima, T., Yaguchi, K., Kawachi, E., Kagechika, H.: "Medicinal Application of Dicarba-closo-dodecaboranes. Relation between Retinoidal Activity and Conformation of Two Aromatic Nuclei."BioMed.Chem.Lett.. 11. 1307-1311 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Sou, S., Takahashi, H., Yamasaki, R., Kagechika, H., Endo, Y., Hashimoto.: "α-Glucosidase Inhibitors with 4,5,6,7-Tetrachlorophtalimide Skeleton with a Cycloalkyl or Dicarba-closo-dodecaborane."Chem.Parm.Bull.. 49. 791-793 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Songkram, C., Yamasaki, R., Takaishi, K., Yamaguchi, K., Kagechika, H., Endo, Y.: "Molecular Construction Based on lcosahedral Carboranes and Aromatic Urea Groups. A New Type of Carboracycles."Tetrahedron Lett.. 42. 5913-5916 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yamamoto, K., Endo, Y.: "Utility of Boron Clusters for Drug Design. Hansch-Fujita Hydrophobic Parameters p of Dicarba-closo-dodecaboranyl Groups."BioMed.Chem.Lett.. 11. 2389-2392 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Endo, Y., Taoda, Y.: "Electronic Effects of 3cosahedral Carboranes: Kinetic Evidence for Interaction between Boron Atom and Nucleophile on the Solvolysis of (o-Carboranyl)benzyl Tosylates."Tetrahedron Lett.. 42. 5327-5331 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Songkram, C., Takaishi, K., Yamaguchi, K., Kagechika, H., Endo, Y.: "Structures of Bis-and Tris(2-phenyl-o-carboran-l -yl)benzenes. Construction of Three-dimensional Structures Converted from Planar Arylacetylenic Arrays"Tetrahedron Lett.. 42. 6365-6368 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Toya, T., Yamaguchi, K., Endo, Y.: "Cyclic Dibenzoylhydrazines Reproducing the Conformation of Ecdyson Agonists, RH-5849. Importance of Hydrogen-bonding Character of NH Group"BioMed.Chem.. 10. 953-961 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Endo, Y., Songkram, C., Yamasaki, R., Tanatani, A., Kagechika, H., Takaishi, K., Yamaguchi, K.: "Molecular Construction Based on lcosahedral Carboranes and Aromatic N,N'-Dimethylurea Groups. Aromatic Layered Molecules and a Transition Metal Complex"J.Organomet.Chem.. 657. 48-58 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Johnsarnuel, J., Byun, Y., Jones, T., Endo, Y., Tjarks, W.: "A New Strategy for Molecular Modeling and Receptor-based Design of Carborane Containing Compounds."J.Organomet.Chem.. 680. 223-231 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Endo, Y., Yoshimi, T., Miyaura, C.: "Boron Clusters for Medicinal Drug Design: Selective Estrogen Receptor Modulators Bearing Carborane"Pure Appl.Chem.. 75. 1197-1205 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Johnsarnuel, J., Byun, Y., Jones, T., Endo, Y., Tjarks, W.: "A Convenient Method for the Computer-Aided Molecular Design of Carborane Containing Compounds."BioMed.Chem.Lett.. 13. 3213-3216 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Endo, Y., Yamamoto, K., Kagechika, H.: "Utility of Boron Clusters for Drug Design. Relation between Estrogen Receptor Binding Affinity and Hydrophobicity of Phenols Bearing Various Types of Carboranyl Groups."BioMed.Chem.Lett.. 13. 4089-4092 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Taoda, Y., Endo, Y.: "Electronic Effects of lcosahedral Carboranes: Mechanistic Alteration in Solvolysis of x-(o-Carboranyl)benzyl Tosylates by Electronic Effect of Substituents"Tetrahedron Lett.. 44. 8177-8181 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Ohta, K., Januszko, A., Kaszynski,, Nagamine, T., Sasnouski, G., Endo, Y.: "Structural Effects in Three-Ring Mesogenic Derivatives of p-Carborane and Their Hydrocarbon Analogs."Liq.Cryst. (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Endo, Y., Yoshimi, T., Miyaura, C: "Utility of Boron Cluster for Drug Design: Selective Estrogen Receptor Modulators (SERMs) Bearing Carborane As a Hydrophobic Skeletal Structure. "Boron Chemistry at the Beginning of the 21 th century"Russian Academy of Sciences, (Nauka, Moscow). 298-306 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Gavel, D., Endo, Y: "Polyboranes in Medicinal Chemistry. "Molecular Clusters of the Main-Group Elements""Wiley-VHC, Weinheim(in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Jayaseharan Johnsamuel: "A New Strategy for Molecular Modeling and Receptor-based Design of Carborane Containing Compounds"J.Organomet.Chem.. 680. 223-231 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Jayaseharan Johnsamuel: "A Convenient Method for the Computer-Aided Molecular Design of Carborane Containing Compounds"BioMed.Chem.Lett.. 13. 3213-3216 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yasuyuki Endo: "Boron clusters for medicinal drug design : Selective estrogen receptor modulators bearing carborane"Pure Appl.Chem.. 75. 1197-1205 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yasuyuki Endo: "Utility of Boron Clusters for Drug Design. Relation between Estrogen Receptor Binding Affinity and Hydrophobicity of Phenols Bearing Various Types of Carboranyl Groups"BioMed.Chem.Lett.. 13. 4089-4092 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yoshiyuki Taoda: "Electronic Effects of Icosahedral Carboranes : Mechanistic Alteration in Solvolysis of a-(o-Carboranyl)benzyl Tosylates by Electronic Effect of Substituents"Tetrahedron Lett.. 44. 8177-8181 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Kiminori Ohta: "Structural Effects in Three-Ring Mesogenic Derivatives of p-Carborane and Their Hydrocarbon Analogs"Liq.Cryst.. In press. (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yasuyuki Endo: "Boron Chemistry at the Beginning of the 21th Century"Bubnov, Yu., et al.(eds.) Russian Academy of Sciences, Nauka, Moscow. 298-306 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Tetsuya Toya: "Potent and selective partial ecdysone agonist activity of chromafenozide in Sf9 cells"Biochem. Biophys. Res. Commun.. 292. 1087-1091 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Yasuyuki Endo: "Molecular construction based on icosahedral carboranes and aromatic N, N'-dimethylurea groups. Aromatic layered molecules and a transition metal complex"J. Organomet. Chem.. 657. 48-58 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tetusya Toya: "Cyclic Dibenzoylhydrazines Reproducing the Conformation of Ecdyson Agonists, RH-5849, Importance of Hydrogen-bounding Character of NH Group"BioMed. Chem.. 10. 953-961 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Yasuyuki Endo: "Structure-Activity Study of Retinoid Agonists with Dicarba-closo-dodecaboranes. Relation between Retinoidal Activity and Conformation of Two Aromatic Nuclei"BioMed.Chem.Lett.. 11. 1307-1311 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Chalermkiat Songkram: "Molecular Construction Based on Icosahedral Carboranes and Aromatic Urea Groups. A New Type of Carboracycles"Tetrahedron Lett.. 42. 5319-5322 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Keisuke Yamamoto: "Utility of Boron Clusters for Drug Design. Hansch-Fujita Hydrophobic Parameters π of Dicarba-closo-dodecaboranyl Groups"BioMed.Chem.Lett.. 11. 2389-2392 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Yasuyuki Endo: "Electronic Effects of Icosahedral Carboranes : Kinetic Evidence. for Interaction between Boron Atom and Nucleophine on the Solvolysis of(o-Carboranyl)benzyl Tosylates"Tetrahedron Lett.. 42. 6327-6331 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Chalermliat Songkram: "Structures of Bis- and Tris(2-phenyl-o-carboran-1-yl)benzenes. Construction of 3-Dimensional Structures Derived from Planar Arylacetylenic Arrays"Tetrahedron Lett.. 42. 6365-6368 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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