Flores Susana, Montenegro Iván, Villena Joan, Cuellar Mauricio, Werner Enrique, Godoy Patricio, Madrid Alejandro
Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile.
Escuela de Obstetricia y Puericultura, Facultad de medicina, Campus de la Salud, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2520000, Chile.
Int J Mol Sci. 2016 Aug 22;17(8):1366. doi: 10.3390/ijms17081366.
A series of novel oxyalkylchalcones substituted with alkyl groups were designed and synthesized, and the antioomycete activity of the series was evaluated in vitro against Saprolegnia strains. All tested O-alkylchalcones were synthesized by means of nucleophilic substitution from the natural compound 2',4'-dihydroxychalcone (1) and the respective alkyl bromide. The natural chalcone (1) and 10 synthetic oxyalkylchalcones (2-11) were tested against Saprolegnia parasitica and Saprolegnia australis. Among synthetic analogs, 2-hydroxy,4-farnesyloxychalcone (11) showed the most potent activity against Saprolegnia sp., with MIC and MOC values of 125 µg/mL (similar to bronopol at 150 µg/mL) and 175 µg/mL, respectively; however, 2',4'-dihydroxychalcone (1) was the strongest and most active molecule, with MIC and MOC values of 6.25 µg/mL and 12.5 µg/mL.
设计并合成了一系列带有烷基取代基的新型氧烷基查尔酮，并对该系列化合物对水霉属菌株的抗卵菌活性进行了体外评估。所有测试的O-烷基查尔酮均通过天然化合物2',4'-二羟基查尔酮（1）与相应的烷基溴经亲核取代反应合成。天然查尔酮（1）和10种合成的氧烷基查尔酮（2-11）针对寄生水霉和澳洲水霉进行了测试。在合成类似物中，2-羟基-4-法尼基氧基查尔酮（11）对水霉属菌株显示出最强活性，其最低抑菌浓度（MIC）和最低杀菌浓度（MOC）值分别为125μg/mL（与150μg/mL的溴硝醇相似）和175μg/mL；然而，2',4'-二羟基查尔酮（1）是最强且活性最高的分子，其MIC和MOC值分别为6.25μg/mL和12.5μg/mL。
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