Synthesis and anti-juvenile hormone activity of alkyl 4-(2-phenoxyalkyloxy) benzoates and related compounds

Kenjiro Furuta, Hiromitsu Shirahashi, Kiyo Ashibe, Hanina Yamashita, Masashi Nishikawa, Norihiro Fujita, Naotaka Yamada, Eiichi Kuwano

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A number of alkyl 4-(2-phenoxyhexyloxy)benzoates and related compounds were synthesized and evaluated their activity to induce precocious metamorphosis in larvae of the silkworm, which was clearly recognized as a juvenile hormone-deficiency symptom. In the alkyl 4-(2-phenoxyhexyloxy)benzoate series, only the methyl and ethyl esters showed precocious metamorphosis-inducing activity. Replacement of the ester group with an ethylcarbamoyl, butanoyl, nitro or a phenoxy group dramatically decreased or eliminated the activity. Both enantiomers of ethyl 4-(4-methyl-2-phenoxypentyloxy)benzoate (13) were prepared by starting with L- and D-leucine. There was no significant difference in precocious metamorphosis-inducing activity between 13R(+)- and 13S(-)-enantiomers. Conversion of the 4-ethoxycarbonyl group of 13 to the corresponding carboxylic acid eliminated the activity, indicating that the methyl or ethyl ester group is indispensable for the activity.

Original languageEnglish
Pages (from-to)303-308
Number of pages6
JournalJournal of the Faculty of Agriculture, Kyushu University
Volume51
Issue number2
Publication statusPublished - Oct 2006

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Agronomy and Crop Science

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