Synthesis and nematocidal activity of aralkyl- and aralkenylamides related to piperamide on second-stage larvae of Toxocara canis

Fumiyuki Kiuchi, Norio Nakamura, Makiko Saito, Kazue Komagome, Hirokuni Hiramatsu, Noriaki Takimoto, Nobuaki Akao, Kaoru Kondo, Yoshisuke Tsuda

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Seventy-nine aralkyl- and aralkenylamides related to piperamides were synthesized and their nematocidal activity against second-stage larvae of dog roundworm, Toxocara canis, was examined. The activity was greatly dependent on the alkyl chain length and the nature of the amine moiety, but was scarcely affected by the presence or absence of double bond(s) in the chain. The alkyl chain lengths which showed the strongest activity in a series of homologues were m=11 for the pyrrolidine amides and m=13 for the N- methylpiperazine amides. Although piperamides (3,4-methylenedioxyphenyl homologues) showed the strongest activity among the homologues tested, methoxy substituent(s) on the aromatic ring did not have much effect on the activity. However, conversion of the methoxy group to a hydroxy group greatly decreased the activity and shortened the chain length giving the strongest activity. Calculated log P values of non-phenolic aryl-piperamides fell in the range from 3.5 to 4.5, whereas those of hydroxyphenyl-piperamides were smaller, suggesting that different mechanisms are involved in the nematocidal activity of phenolic and non-phenolic compounds.

Original languageEnglish
Pages (from-to)685-696
Number of pages12
JournalChemical and Pharmaceutical Bulletin
Volume45
Issue number4
DOIs
Publication statusPublished - 1997 Apr

Keywords

  • Toxocara canis
  • hydrophobicity
  • nematocidal activity
  • piperamide
  • structure activity relationship
  • synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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