2-氰基-3-取代胺基-3-[2-(4-氟苯基)-乙胺基]丙烯酸乙酯类化合物的合成及生物活性研究

摘要/Abstract

以氰基乙酸乙酯为原料, 经与二硫化碳、硫酸二甲酯反应合成了2-氰基-3,3-二甲硫基丙烯酸乙酯(1), 然后引入对氟苯乙胺得到化合物(3), 其与脂肪胺反应合成了新型含对氟苯乙氨基的2-氰基丙烯酸乙酯类化合物5a～5h, 其结构经元素分析, IR, ¹H NMR和¹³C NMR等确证. 初步生物活性试验表明, 部分化合物具有一定抗烟草花叶病毒活性.

关键词: 2-氰基丙烯酸乙酯类化合物, 4-氟苯乙胺, 合成, 结构, 生物活性

Abstract A series of ethyl 2-cyano-3-substituted-amino-3-[2-(4-fluorophenyl)-ethylamino]-acrylates were synthesized in three steps. Firstly, ethyl 2-cyano-3,3-dimethythioacrylate (1) was prepared from reactions of ethyl cyanoacetate with carbon disulfide and dimethyl sulfate. Secondly, it reacted with 4-fluorophenethylamine to yield ethyl 2-cyano-3-methythioacrylate-3-[2-(4-fluorophenyl)-ethylamino]- acrylate (3). Thirdly, the title compounds 5a～5h were obtianed by the reactions of 3 with corresponding alkylamines. The structures of as-synthesized compounds were confirmed by elemental analysis, IR, ¹H NMR and ¹³C NMR techeniques. Preliminary bio-assay test indicated that some compounds showed moderate antivirus activity against Tobacco mosaic vi-rus.

Key words: ethyl 2-cyanoarcylate, 4-fluorophenethylamine, synthesis, structure, bioactivity

引用此文

周进康, 宋宝安, 薛伟, 金林红, 干正洋. 2-氰基-3-取代胺基-3-[2-(4-氟苯基)-乙胺基]丙烯酸乙酯类化合物的合成及生物活性研究[J]. 有机化学, 2011, 31(06): 865-869.

ZHOU Jin-Kang, SONG Bao-An, XUE Wei, JIN Lin-Hong, GAN Zheng-Yang. Synthesis and Bioactivity of Ethyl 2-Cyano-3-substituted-amino- 3-[2-(4-fluorophenyl)-ethylamino]-acrylates[J]. Chin. J. Org. Chem., 2011, 31(06): 865-869.

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