| Project/Area Number |
03660141
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
製造化学・食品
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| Research Institution | KYUSHU UNIVERSITY |
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Principal Investigator |
ETO Morifusa Kyushu University, Agriculture , Professor, 農学部, 教授 (70038173)
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| Co-Investigator(Kenkyū-buntansha) |
KUWANO Eiichi Kyushu University, Agriculture , Associate Professor, 農学部, 助教授 (00108672)
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| Project Period (FY) |
1991 – 1992
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| Project Status |
Completed (Fiscal Year 1992)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1991: ¥1,200,000 (Direct Cost: ¥1,200,000)
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| Keywords | Insect growth regulators / JH esterase / Ace-tylcholinesterase / Glutathione-dependent enzymes / Anti-GABA organophosphates / Octopaminergic compounds / Tryptophan synthetase inhibitors / Plant growth regulators / 遷移状態アナログ / トリフルオロ酢酸アミド / 1,5-二置換イミダゾール / 複素環チオール / ジヒドロインドール / 植物生長抑制 / 昆虫生育制御 / トリフロルメチルケトン / メルカプトベンツイミダゾ-ル / メルカプトピリジン / ジヒドロインド-ル / アセチルコリンエステラ-ゼ阻害 |
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| Research Abstract |
Molecular designs for enzyme inhibitors were tried in order to find lead compounds of growth regulators for plants and insects by considering particularly transition-state analogues. Analogues of active intermediates, multi-substrates, and ground-state substrates were also considered.
Inhibitors of the synthetase of tryptophan, an essential amino acid, must be effective as plant-growth regulators without deleterious mammalian effects. 3-(Substituted)-dihydroindoles potently inhibited the enzyme as putative transition-state analogues and retarded the growth of plants. Some thiols derived from substituted benzimidazoles, oxadiazoles, and triazoles also showed high activity to inhibit both tryptophan synthetase and plant-growth. Protection of the thiol group by acylation gave the good in vivo effect.
Trifluoromethylketones and trifluoroacetate derivatives were designed for insect esterase inhibitors. Metamorphosis of silkworm larvae was suppressed by N-(p-phenoxyphenoxy-ethyl) trifluoroacetamide which was designed as a candidate inhibitor for insect juvenile hormone esterase. On the other hand, p-(N,N-diisopropylaminomethyl)trifluoroacetophenone inhibited acetylcholinesterase. 1,5-Disubstituted imidazoles were designed to inhibit cytochrome P450s which participate in the synteses of juvenile hormone in insects and of gibberellin in plants. Some imidazole derivatives induced precocious metamorphosis in silkworm larvae and some others retarded growth of plants.
As multi-substrate analogue of glutathione-dependent enzymes S-substituted glutathiones were synthesized. S-(1-naphthylmethyl) glutathione inhibited glyoxalase I as well as glutathione S-transferase. Bicyclic phosphates with anti-GABA activity and octopamine related compounds were also studied.
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