Synthesis and Antiviral Activities of Pyrazole Derivatives Containing an Oxime Moiety
Synthesis and Antiviral Activities of Pyrazole Derivatives Containing an Oxime Moiety
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DOI：
10.1021/jf802489e
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发表时间：
2008-11-12
影响因子：
6.1
通讯作者：
Zeng, Song
中科院分区：
文献类型：
--
作者：
Ouyang, Guiping;Cai, Xue-Jian;Zeng, Song
1-取代苯基-3-甲基-5-取代苯硫基-4-吡唑肟（3）与氯甲基化杂环化合物（CICH 2-R-3）在乙醇中回流反应得到目标化合物4a-n。4a-e在室温下用KMnO_4在HOAc中氧化得到8个新化合物5a-h。所合成的化合物通过物理常数进行了表征，其结构经IR，H-1 NMR，C-13 NMR和元素分析确证。生物活性测定结果表明，这些化合物具有一定的抗病毒活性。结果表明，标题化合物4a和4g对烟草花叶病毒（TMV）具有与商品宁南霉素（EC_（50）= 52.7 μ g/mL）相同的灭活效果（EC_（50）= 58.7和65.3 μ g/mL）。据我们所知，这是第一个报告的抗病毒活性的吡唑衍生物含有肟部分。
Target compounds 4a-n were obtained by the reaction of 1-substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaidoximes (3) with chloromethylated heterocyclic compounds (CICH2-R-3) under reflux conditions in ethanol. Subsequently, the oxidation of 4a-e with KMnO4 in HOAc at room temperature afforded eight new compounds, 5a-h. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were confirmed by IR, H-1 NMR, C-13 NMR, and elemental analysis. The bioassay revealed that the compounds possessed antiviral activities. It was found that title compounds 4a and 4g had the same inactivation effects against TMV (EC50 = 58.7 and 65.3 mu g/mL) as the commercial product Ningnanmycin (EC50 = 52.7 mu g/mL). To the best of our knowledge, this is the first report on the antiviral activity of pyrazole derivatives containing an oxime moiety.