廖鹏, 胡仕琴, 张宏, 刘静姿. 寡肽手性膦酸酯硫脲的合成及其抗烟草花叶病毒活性[J]. 农药学学报, 2018, 20(2): 153-162. DOI: 10.16801/j.issn.1008-7303.2018.0020
    引用本文: 廖鹏, 胡仕琴, 张宏, 刘静姿. 寡肽手性膦酸酯硫脲的合成及其抗烟草花叶病毒活性[J]. 农药学学报, 2018, 20(2): 153-162. DOI: 10.16801/j.issn.1008-7303.2018.0020
    LIAO Peng, HU Shiqin, ZHANG Hong, LIU Jingzi. Synthesisandanti-tobaccomosaicvirusactivityofoligopeptidechiralthioureascontainingphosphonatemoiety[J]. Chinese Journal of Pesticide Science, 2018, 20(2): 153-162. DOI: 10.16801/j.issn.1008-7303.2018.0020
    Citation: LIAO Peng, HU Shiqin, ZHANG Hong, LIU Jingzi. Synthesisandanti-tobaccomosaicvirusactivityofoligopeptidechiralthioureascontainingphosphonatemoiety[J]. Chinese Journal of Pesticide Science, 2018, 20(2): 153-162. DOI: 10.16801/j.issn.1008-7303.2018.0020

    寡肽手性膦酸酯硫脲的合成及其抗烟草花叶病毒活性

    Synthesisandanti-tobaccomosaicvirusactivityofoligopeptidechiralthioureascontainingphosphonatemoiety

    • 摘要: 为了寻找新型具有抗烟草花叶病毒 (TMV) 作用的化合物,在前期研究工作基础上,以取代苄胺、氨基酸及亚膦酸二烷基酯等为原料,按照由C端向N端依次接肽的合成策略,采用缩合剂O-苯并三氮唑-四甲基脲六氟膦酸酯 (HBTU) 合成酰胺的方法,获得了18个新型寡肽手性膦酸酯硫脲,其结构均经红外光谱、(1H、13C、31P、19F) NMR及元素分析确证和表征,并首次研究了该类化合物抗TMV活性。结果表明:部分目标物对TMV具有较高治疗作用,其中化合物 5i5j5p 在500 μg/mL时对TMV侵染的活体治疗作用效果分别为52.6%、55.7%和56.1%,接近对照药剂宁南霉素 (55.4%)。值得进一步结构改造和构型优化,并在此基础上进行作用机制研究。

       

      Abstract: In order to develop more effective anti-tobacco mosaic virus (TMV) agents, 18 noval oligopeptide chiral thioureas containing phosphonate moiety have been synthesized. Substituted benzylamines, amino acids and dialkyl phosphonate were employed as the starting materials. C-to-N synthesis strategy and coupling reagent O-benzotriazole-N,N,N′,N′-tetramethylurea(HBTU) were used. The structures of the target compounds were characterized by IR, (1H, 13C, 31P, 19F) NMR and elemental analysis. The Anti-TMV activities of target compounds were evaluated for the first time. The results indicate that these compounds have a high therapeutic effect on TMV, and exhibit good anti-plant virus activities. The curative rates of 5i , 5j and 5p against TMV were 52.6%, 55.7% and 56.1%, respectively, which were comparable to the curative rate (55.4%) of the commercial reference ningnanmycin.

       

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