| Project/Area Number |
06555278
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Niigata University |
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Principal Investigator |
ANDO Masayoshi Niigata University, Professor, 工学部, 教授 (40004402)
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| Co-Investigator(Kenkyū-buntansha) |
YAMAZAKI Hiroko Sumitomo Chemical Co., LTD., Agricultural Chemicals Research Laboratory, Researc, 宝塚総合研究所・農業科学研究所, 副主任研究員
HIRATA Naonori Sumitomo Chemical Co., LTD., Agricultural Chemicals Research Laboratory, Chief R, 宝塚総合研究所・農業科学研究所, 首席研究員
SUZUKI Toshio Niigata University, Assistant Professor, 工学部, 助教授 (80202133)
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| Project Period (FY) |
1994 – 1995
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| Project Status |
Completed (Fiscal Year 1995)
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| Budget Amount *help |
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1995: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1994: ¥2,300,000 (Direct Cost: ¥2,300,000)
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| Keywords | Antinflammatory Drugs / Intercellular Adhesion Molecule (ICAM-1) / Santonine Derivatives / Agricultural Disinfectant / Termiticide / Chamaecinone Derivatives / Plant Growth Retardant / Guaianolides / サントニン / ツベレフェリン / デヒドロコスタスラクトン / カメシノン / 殺白蟻活性 |
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| Research Abstract |
1.Development of the new type of antinflammatory drugs
3-Oxoeudesmano-13,6-lactones which possess modified functional groups at C_2, _3, _<11> and isomerized stereochemistry at C_6 were systematically derived from santonine, and were screened for inhibitors of inductive activity of intercellular adhesion molecule (ICAM-1). Structure-activity relationship indicated that a carbonyl group at C_3, a bromo group or double bond at C_2, and a methylene group at C_<11> play an important role for the inhibitory activity. Concerning the C_6 stereochemistry, alpha-isomer showed stronger inhibitory activity in the case of the C_<11>-methyl derivative. On the other hand, beta-isomer was superior in the case of the C11-metylene derivative (alpha-metylene-gamma-lactone). 2alpha-Bromo-3-oxoeudesmano-13,6alpha-lactone and 13,6beta-lactone strongly inhibited the inductive activity of ICAM-1. Furtherly they showed the strong inhibitory activity on leukocyte migration in rat air pouch inflammation. They are expected for the new type of an antirheumatic and an antiallergic drug.
2.Development of agricultural disinfectants
Eudesmano-13,6alpha-lactones derived from santonine were screened for agricultural disinfectants, and 16 kinds of compounds showed the strong activity. On the other hand, eudesmano-13,6beta-lactones were similarly screened, and 7 kinds of compounds showed strong activity. It is interesting to note that the stereoisomers at C_6 effect on the different plant diseases.
3.Development of termiticides
Based on the structure-activity relationship between chamaecinone derivatives possessing the cis-fused AB-ring and the termiticidal activity, new derivatives modified on the A-ring were synthesized. Study of the structure-activity relationship is undergoing.
4.Development of plant growth retardants
4 kinds of guaianolides derived from santonine showed the auxin-like activity in a moderate degree.
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