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DESIGN, SYNTHESIS, AND PROPERTIES OF CYCLOPHANES AS HOSTS HAVING ABILITY OF FORMING INCLUSION COMPLEXES

Research Project

Project/Area Number 63470126
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionFACULTY OF PHARMACEUTICAL SCIENCES, THE UNIVERSITY OF TOKYO

Principal Investigator

KOGA Kenji  Univ. of Tokyo Fac. Pharm. Sci. Professor, 薬学部, 教授 (10012600)

Co-Investigator(Kenkyū-buntansha) SASAKI Shigeki  Univ. of Tokyo Fac. Pharm. Sci. Assistant Professor, 薬学部, 助手 (10170672)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥7,600,000 (Direct Cost: ¥7,600,000)
Fiscal Year 1989: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1988: ¥4,700,000 (Direct Cost: ¥4,700,000)
KeywordsWater-soluble Cyclophanes / Molecular Recognition / Diarylmethane / Inclusion Complex / Host-Guest Chemistry / Inclusion of Cationic Guests / カチオン性シクロファン / アニオン性フィクロファン / ホストゲスト錯体 / クロマトグラフィー用担体 / 疎水性相互作用 / 電荷相互作用
Research Abstract

Our earlier studies on cyclophanes such as QCP44 have suggested that they form inclusion complexes with anionic and neutral hydrophobic guests in aqueous solution. We intended to introduce the cyclophanes to stationary phase of column chromatography, and to design novel macrocyclic compounds as hosts for cationic guests.
The skeleton of QCP44 was introduced to agarose gel with amide bond, and some structural isomers, such as 1- or 2-naphthalane sulfonic acids, could be effectively separated by the column containing this gel.
Novel cyclophanes having carboxylates, ACP44 and ACP66, were synthesized, and were found to form stable 1:1 complexes with cationic guests. Stability constants (Ks) of their complexes were obtained using ^1H-NMR technique (Table 1). ACP44 exhibited the greatest value of K s for the complex with 1,4-bis(trimethylammoniummethyl)benzene. In contrast, ACP66 formed the most stable complex with 1,3-bis(trimethylammonium)propane.
Investigation on novel macrocycles for selective and efficient artificial catalysts as an enzyme model is now in progress.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] Kenji Koga: "Cyclophanes as Hosts for Aromatic and Aliphatic Guests" Journal of Inclusion Phenomena. 7. 53-60 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kazunori Odashima: "Molecular Recognition and Discrimination of Hydrophobic Guests in Water by Quaternary Ammonium cyclophanes Having Diarylmethane" Chemical and Pharmaceutical Bulletin. 37. 257-259 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 佐々木茂貴: ""クラウンエ-テル・クリプタンド"" 有機合成化学協会誌. 47. 493-502 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kenji Koga: "Functionalization of Crown Ethers" Pure and Applied Chemistry. 60. 539-543 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 古賀憲司: ""分子認識能を有する純人工ホスト化合物の開発と応用","包接化合物の基礎と応用",戸田芙三夫監修" エヌ・ティ-・エス, 32 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kenji Koga: "Cyclophanes as Hosts for aromatic and Aliphatic Guests" J. Inclusion Phenomena, 7, 53-60, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kazunori Odasima: "Molecular Recognition and Discrimination of Hydrophobic Guests in Water by Quaternary Ammonium Cyclophanes Having Diarylmethane Units" Chem. Pharm. Bull., 37, p257-259, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shigeki Sasaki: "Crown Ethers and Cryptands" J. Syn. Org. Chem., 47, 493-502, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kenji Koga: "Functionalization of Crown Ethers" Pure Appl. Chem.,.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kenji Koga: "Cyclophanes as Hosts for Aromatic and Aliphatic Guests" Journal of Inclusion Phenomena. 7. 53-60 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kazunori Odashima: "Molecular Recognition and Discrimination of Hydrophobic Guests in Water by Quaternary Ammonium cyclophanes Having Diarylmethane Units" Chemical and Pharmaceutical Bulletin. 37. 257-259 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 佐々木茂貴: ""クラウンエ-テル・クリプタンド"" 有機合成化学協会誌. 47. 493-502 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kenji Koga: "Functionalization of Crown Ethers" Pure and Applied Chemistry. 60. 539-543 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] 古賀憲司: Pure & Applied Chemstry. 60. 539-543 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 古賀憲司: J.Inclusion Phenomena. 7. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] 小田嶋和徳: Chem.Pharm.Bull. 37. (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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