Quantitative structure-activity relationship analysis of antifungal (+)-dihydroguaiaretic acid using 7-phenyl derivatives.
The relationship between antifungal activity against Alternaria alternata and structure on the 7-phenyl group of (+)-dihydroguaiaretic acid ((+)-DGA) was clarified by employing 38 synthesized (+)-DGA derivatives. The results were identified by quantitative structure-activity relationship (QSAR) analysis employing the Hansch-Fujita method. Some compounds showed higher activity than (+)-DGA. The compound showing highest activity was 3,5-difluorophenyl derivative 37. It was suggested that the small electron-withdrawing group at the meta-position of the 7-phenyl group is important for the higher activity by antifungal test and Hansch-Fujita analysis. The whitening activity of 3-hydroxy-4-methoxyphenyl derivative 28, 3-hydroxy-4-ethoxyphenyl derivative 29, and 3-hydroxy-4-isopropoxyphenyl derivative 30 against A. alternata Japanese pear pathotype was also discovered.
Faculty of Agriculture and ‡Integrated Center for Sciences, Tarumi Station, Ehime University , 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
Ayaka
A
Hasebe
Hisashi
H
Nishiwaki
Koichi
K
Akiyama
Takuya
T
Sugahara
Taro
T
Kishida
Satoshi
S
Yamauchi
D000528:Alternaria / Q000187:drug effects; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology*; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D017705:Lignans / Q000737:chemistry* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship
D005659:Fungicides, Industrial; D017705:Lignans; C015816:dihydroguaiaretic acid; D006139:Guaiacol