5-Aryl-1,3,4-oxadiazole-2-thiols as a new series of trans-cinnamate 4-hydroxylase inhibitors

Naotaka Yamada, Yuki Kataoka, Takamichi Nagami, Soonsung Hong, Shinya Kawai, Eiichi Kuwano

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A series of 5-aryl-1,3,4-oxadiazole-2-thiols was found to inhibit trans-cinnamate 4-hydroxylase (C4H) from Populus kitakamiensis, which was expressed in yeast. 5-Phenyl-1,3,4-oxadiazole-2-thiol showed inhibitory activity comparable to 2-hydroxy-1-naphthoic acid, a known C4H inhibitor. Studies on the structure-activity relationship indicated that the presence of a thiol group was significant for stronger activity. Of the compounds tested, 5-(3-fluorophenyl)-1,3,4-oxadiazole-2-thiol was the most active.

Original languageEnglish
Pages (from-to)205-208
Number of pages4
JournalJournal of Pesticide Science
Volume29
Issue number3
DOIs
Publication statusPublished - Dec 1 2004

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Trans-Cinnamate 4-Monooxygenase
trans-cinnamate 4-monooxygenase
thiols
Sulfhydryl Compounds
Populus
Structure-Activity Relationship
structure-activity relationships
Yeasts
yeasts
1,3,4-oxadiazole
acids

All Science Journal Classification (ASJC) codes

  • Insect Science

Cite this

5-Aryl-1,3,4-oxadiazole-2-thiols as a new series of trans-cinnamate 4-hydroxylase inhibitors. / Yamada, Naotaka; Kataoka, Yuki; Nagami, Takamichi; Hong, Soonsung; Kawai, Shinya; Kuwano, Eiichi.

In: Journal of Pesticide Science, Vol. 29, No. 3, 01.12.2004, p. 205-208.

Research output: Contribution to journalArticle

Yamada, Naotaka ; Kataoka, Yuki ; Nagami, Takamichi ; Hong, Soonsung ; Kawai, Shinya ; Kuwano, Eiichi. / 5-Aryl-1,3,4-oxadiazole-2-thiols as a new series of trans-cinnamate 4-hydroxylase inhibitors. In: Journal of Pesticide Science. 2004 ; Vol. 29, No. 3. pp. 205-208.
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