Synthesis and Biological Activity of 4-(Pyridin-3-yl)-2-hydroxy-4-oxobut-2-enoic Acid Derivatives

Alena L. Stalinskaya, Zarina Shulgau, Т. М. Сейлханов, Alexey S. Vasilchenko, Samat A. Talipov, Ivan V. Kulakov

2019

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DOI 10.1055/s-0037-1610738
Data confidence 70 medium
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Abstract

Claisen condensation reaction of diethyl oxalate with 1-[4-(furan-2-yl)-2-methyl-5-nitro-6-phenylpyridin-3-yl]ethan-1-one afforded (Z)-4-[4-(furan-2-yl)-2-methyl-5-nitro-6-phenylpyridin-3-yl]-2-hydroxy-4-oxobut-2-enoic acid. The latter reacted with various binucleo­philes to form the corresponding 3,4-dihydroquinoxaline-2(1H)-one, 3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one, and 1H-pyrazole derivatives. Biological screening of the obtained compounds revealed analgesic and antibacterial activity.