Preparation and root growth-modulatory activity of N-substituted 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides.
N-Substituted 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides (8) were synthesized through the reaction of amines (13) with 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanoic acid (3b), which was prepared via condensation of 2-(bromomethyl)furan (10b) with diethyl acetamidomalonate, followed by partial hydrolysis of the resultant diethyl ester (3a) in the presence of barium hydroxide. However, bulky amines such as tert-butylamine or 2-trifluoromethylaniline did not afford the corresponding diamides (8). The biological activity of the prepared diamides (8) as root growth modulators was examined by germination assay using rape and leek seeds. N-(5-Bromo-2-thiazolyl)- and N-(4-chloro-2-benzothiazolyl)-2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides (8h, i) both potently inhibited the root growth of rape seedlings, but were less effective in the case of leek seeds. The herbicide 2,4-dichlorophenoxyacetic acid completely inhibited root growth in both cases.
Kitagawa
T
T
Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University, Japan. kitagawa@pharm.kobegakuin.ac.jp
Akiyama
N
N
Masai
K
K
D000473:Alkanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology*; D001937:Brassica / Q000254:growth & development; D003864:Depression, Chemical; D018525:Germination / Q000187:drug effects; D006868:Hydrolysis; D019697:Onions / Q000254:growth & development; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000494:pharmacology*; D018517:Plant Roots / Q000187:drug effects* / Q000254:growth & development*
D000473:Alkanes; D000577:Amides; D010937:Plant Growth Regulators