G. Merlin, F. Nurit, P. Ravanel
1987
Citations
0
Influential Citations
5
Citations
Journal
Phytochemistry
Abstract
Abstract A N -(1,1-dimethylpropynyl) benzamide series was obtained by changing the substitution of the phenyl on the 3 or 4 position. As is the case for propyzamide, N -(1,1-dimethylpropynyl)-3-chlorobenzamide is a powerful and selective inhibitor of mitosis in plant cells at 0.1 μM, as is demonstrated by its characteristic effect on seedlings of five different species ( Triticum sativum L., Avena fatua L., Lolium multiflorum Lam., Raphanus sativus L., Sinapis arvensis L.), by the effects on dividing cells and by the lack of effect on mitochondria or chloroplast activities. Three other compounds of the series inhibit mitosis at 10 μM (3-Br, 3-Me, 3-F). The 4-substituted derivatives, as well as the 3-CN or 3-OMe benzamides have only a small effect on cell division. All these results can be explained by a quantitative structure-activity relationship where the lipophilicity (expressed by π), the electronic activity (expressed by σ) and a steric character expressed by L (illustrating the steric hindrance near the 3 and 4 positions of the phenyl ring) are taken into account. These observations suggest that the 4 position of the phenyl is probably directly involved in the binding of the propyzamide derivatives to a target controlling mitosis in plant cells.