Determination of stereoselective interaction between enantiomers of chiral gamma-aryl-1H-1,2,4-triazole derivatives and Penicillium digitatum.
A series of chiral gamma-aryl-1H-1,2,4-triazole derivatives has been synthesized and the respective analogues have been tested for their inhibitory activities against Penicillium digitatum (P. digitatum). In vitro experiments were indicative of a strong inhibitory effect of all of the compounds on P. digitatum, and seven of the compounds 5 exhibited better inhibition than the commercial fungicides triadimefon and triadimenol. The respective pairs of enantiomers showed significantly different inhibitory activities, most notably in the case of 5g-R and 5g-S, for which a 230-fold difference was observed. These observations suggest that P. digitatum discriminates the enantiomers and that the R enantiomer better fits the active site of cytochrome P450.
Cao
Xiufang
X
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China.
Hu
Ming
M
Zhang
Jie
J
Li
Fei
F
Yang
Yuhong
Y
Liu
Deli
D
Liu
Sheng Hua
SH
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001665:Binding Sites; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000378:metabolism; D005656:Fungal Proteins / Q000737:chemistry / Q000378:metabolism; D010407:Penicillium / Q000737:chemistry / Q000187:drug effects* / Q000201:enzymology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000935:Antifungal Agents; D005656:Fungal Proteins; D014230:Triazoles; C045575:1,2,4-triazole; D003577:Cytochrome P-450 Enzyme System