Preparation and root growth-inhibitory activity of N-substituted 2-(2-chloroacetamido)-3-(furan-2-yl)propanamides.
A series of N-substituted 2-(2-chloroacetamido)-3-(furan-2-yl)propanamides (16--18) was prepared through the reaction of chloroacetyl chloride with N-substituted 2-amino-3-(furan-2-yl)propanamides (15), which were obtained via condensation of 2-(tert-butoxycarbonylamido)-3-(furan-2-yl)propanoic acid (Boc-furylalanine) (8) with amines (9, 11, 13), followed by hydrolysis of the resultant N-substituted Boc-furylalanine acid amides (10, 12, 14) in the presence of HCl/dioxane. The biological activity of the prepared 16, 17 and 18 as root growth inhibitors was examined by germination assay using rape seed. At the concentration of 5.0 x10 (-5) M, the most active compound, 2-(2-chloroacetamido)-N-(2,6-diethylphenyl)-3-(furan-2-yl)propanamide (16 n), showed potent root growth-inhibitory activity of 76% towards rape seedlings.
Kitagawa
Tokujiro
T
Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University;Ikawadani, Nishi-ku, Kobe 651-2180, Japan. kitagawa@pharm.kobegakuin.ac.jp
Asada
Makoto
M
D000577:Amides / Q000737:chemistry* / Q000494:pharmacology*; D029741:Brassica rapa / Q000254:growth & development; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology*; D006540:Herbicides / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000577:Amides; D005663:Furans; D006540:Herbicides; D007202:Indicators and Reagents