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 journalArticle

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 1 2006

Fingerprint

precocious metamorphosis
Juvenile Hormones
Benzoates
benzoates
juvenile hormones
Esters
esters
enantiomers
synthesis
Bombyx
carboxylic acids
Carboxylic Acids
Leucine
signs and symptoms (animals and humans)
leucine
Larva
insect larvae

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Agronomy and Crop Science

Cite this

Furuta, K., Shirahashi, H., Ashibe, K., Yamashita, H., Nishikawa, M., Fujita, N., ... Kuwano, E. (2006). Synthesis and anti-juvenile hormone activity of alkyl 4-(2-phenoxyalkyloxy) benzoates and related compounds. Journal of the Faculty of Agriculture, Kyushu University, 51(2), 303-308.

Synthesis and anti-juvenile hormone activity of alkyl 4-(2-phenoxyalkyloxy) benzoates and related compounds. / Furuta, Kenjiro; Shirahashi, Hiromitsu; Ashibe, Kiyo; Yamashita, Hanina; Nishikawa, Masashi; Fujita, Norihiro; Yamada, Naotaka; Kuwano, Eiichi.

In: Journal of the Faculty of Agriculture, Kyushu University, Vol. 51, No. 2, 01.10.2006, p. 303-308.

Research output: Contribution to journalArticle

Furuta, K, Shirahashi, H, Ashibe, K, Yamashita, H, Nishikawa, M, Fujita, N, Yamada, N & Kuwano, E 2006, 'Synthesis and anti-juvenile hormone activity of alkyl 4-(2-phenoxyalkyloxy) benzoates and related compounds', Journal of the Faculty of Agriculture, Kyushu University, vol. 51, no. 2, pp. 303-308.
Furuta, Kenjiro ; Shirahashi, Hiromitsu ; Ashibe, Kiyo ; Yamashita, Hanina ; Nishikawa, Masashi ; Fujita, Norihiro ; Yamada, Naotaka ; Kuwano, Eiichi. / Synthesis and anti-juvenile hormone activity of alkyl 4-(2-phenoxyalkyloxy) benzoates and related compounds. In: Journal of the Faculty of Agriculture, Kyushu University. 2006 ; Vol. 51, No. 2. pp. 303-308.
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