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1990 Fiscal Year Final Research Report Summary

Design Synthesis and Receptor Monitoring of Insect Juvenile Hormone Mimetics

Research Project

Project/Area Number 01560149
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionKyoto University

Principal Investigator

IWAMURA Hajime  Kyoto Univ. Agric. Chem. Professor, 農学部, 教授 (30026570)

Project Period (FY) 1989 – 1990
KeywordsInsect juvenile hormone / Oxime O-ethers / Ethers / Amines / Active Structure / Electrostatic Potential
Research Abstract

Series of 4-alkyphenoxyalkanaldoxime O-ethers and corresponding ether and amine derivatives were prepared as insect juvenile hormone (JH) mimetics. The activity examined against Culex pipiens (common mosquito) of the most potent member of each class was comparable to that of the most active JH mimetics so far known. Their structure-activity profiles were in common with those revealed previously by us for other JH-active compounds in the optimum length of the molecule (about 21 A) and the favorable dimensions of the molecular ends. To know the role of the functional group built in the molecule, the electrostatic potential were computed to show that the contours of the potentials commonly had a negative peak when viewed in the plane that perpendicularly bisects their skeletal plane. On the basis of this, the stereochemical interpretations was made and suggested that the most active members in each class are the entities the dimensions of which satisfy the optimum stereochemical condition … More s proposed previously by us for other types of JH mimetics, and the electrostatic negative peak comes on the site about 4.6 A distant from the molecular end. The interaction of the functional group with the receptor was suggested to be an position specific, electronic one in nature. The set of investigation was extended to (4-substituted)-phenoxyalkyl compounds having various nitrogenous and oxygenous functions, such as ester, amide, carbamate and urea, and also to compounds having aromaricfunctions like benzene and pyridine. The compounds synthesized included those having the potency as high as or higher than methoprene, one of the highest active JH-mimetic so far known, and their structural characteristics were common to those observed for the most potent compounds described above, asain satisfying the electrostatic and stereochemical considerations. The receptive site of insect juvenile hormones and their mimetics was suggested to be the entity the diameter size of which is about 21 A, and, within this flamework, it constitutes a kind of cavity at both ends and has an electros totically negative point at the site about 4.6 A distant from one end. Less

  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] Tetsuyoshi Hayashi: "Development of 4ーalkylphenyl aralkyl ethers and related compounds as potent insect juvenile hormone mimetics and structural aspects of their activity." Journal of Agricultural and Food Chemistry. 38. 1965-1971 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tetsuyoshi Hayashi: "Electrostatic and stereochemical aspects of insect juvenile hormone active compounds:A clue for high activity." Journal of Agricultural and Food Chemistry. 38. 1972-1977 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tetsuyoshi Hayashi: "Development of 4-alkylphenyl aralkyl ethers and related compounds as potent insect juvenile hormone mimetics and structural aspects of their activity." Journal of Agricultural and Food Chemistry. 38-10. 1965-1971 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tetsuyoshi Hayashi: "Electrostatic and stereochemical aspects of insect juvenile hormone active compounds : A clue for high activity" Journal of Agricultural and Food Chemistry. 38-10. 1972-1977 (1990)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-08-12  

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