Structure-Activity Relationship in Nematocidal Activity of Piperamides and Malabaricones
| Project/Area Number |
06672096
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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 |
Chemical pharmacy
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| Research Institution | Kanazawa University |
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Principal Investigator |
KIUCHI Fumiyuki Kanazawa University, Graduate School of Natural Science and Technology, Research Assistant, 自然科学研究科, 助手 (60161402)
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| Co-Investigator(Kenkyū-buntansha) |
KONDO Kaoru Kanazawa University, School of Medicine, Associate Professor, 医学部, 助教授 (00079724)
TSUDA Yoshisuke Kanazawa University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (40077508)
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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 |
¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1995: ¥600,000 (Direct Cost: ¥600,000)
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| Keywords | Nematocidal activity / Visceral larva migrans / Piperamide / Structure-activity relationship / Malabaricone / Pyrrolidine amide / N-Methylpiperazine amide / Toxocara canis / N‐メチルピペラジンアミド |
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| Research Abstract |
Seventy six piperamides and their analogs with twenty malabaricones and their analogs were synthesized and their nematocidal activity against second-stage larvae of dog roundworm, Toxocara canis, were examined. Among the piperamide analogs, the activity was largely dependent on the length of the alkyl chain and the nature of the amine moiety. The alkyl chain length which showed the strongest activity in a series of homologues were m=9 for the pyrrolidine amides and m=11 for the N-methylpiperazine amides. Calculated log P values of the activity of these compounds.
Among the naturally occurring malabaricones which have two oxygen functions at both o-and o'-positions of the acetophenone moiety, malabaricone A showed the strongest activity. Among the synthetic malabaricone analogs without any substituent on the aryl moiety, at least one free hydroxy group was essential for the activity. A hydroxy group at the ortho position or at the benzylic position (introduced by reduction of the ketone or conjugation with the hydroxy group on the benzene ring) of the acetophenone moiety seemed to be important for the activity.
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Report
(3 results)
Research Products
(7 results)
