Synthesis and Bioactivity of Ethyl 2-Cyano-3-substituted-amino- 3-[2-(4-fluorophenyl)-ethylamino]-acrylates

Abstract

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

Cite this article

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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References

[1]Phillips, J, N.; Huppatz, J.L..Cyanoacrylate inhibitors of the reaction V-- The effect of chirality on inhibitor binding[J].J. Z. Naturforsch,1987,42C:684-689

[2]Liu, H Y; Yang, G, F; Lu, R, J.; Yang, H, Z.; Lai, L. H..Studes on Bio-rational Design of Photosystem II Inhibitors(II)---The Crystal and Molecular Stucture of Ethyl 3-Benzylamino-2-cyano-3-methylthioacrylate[J].Chem, J, Chin, Univ,1998,19(6):899-902

[3]刘华银,杨光富,陆荣健, 杨华铮,来鲁华.生物合理设计光系统Ⅱ抑制剂研究Ⅱ――3-苯甲氨基-2-氰基-3-甲硫基丙烯酸乙酯的晶体及分子结构[J].高等学校化学学报,1998,19(6):899-902

[4]Liu, H , Y; Sha, Y, L; Tan, H, F; Yang, H, Z; Lai, L, H . .Bio-rational design of Photosystem II inhibitors (VIII) ---Molecular design, synthesis and inhibitory activity of acrylates(acrylamides)[J].Sci. China, Ser. B,1999,42(3):326-331

[5]Sun, H, K; Wang, Q, M; Huang, R , Q; Heng, L ; Li, Y, H. .Synthesis and biological activity of novel cyanoacrylates containing ferrocenyl moiety[J].J Organometallic Chem,2002,655:182-185

[6]Wang, Q, M; Sun, H, K; Huang, R, Q..Synthesis and Herbicidal Activity of (Z)- Ethoxyethyl2-cyano-3-(2-methyl-thio-5-pyridylmethylamino)acrylates[J].J, Heteroatom, Chemistry,2004,15(1):67-70

[7]Gao, Y; Cheng, X, F; Liu, B, Zou, x, M; Fu, F, Z; Yang, H, Z..Synthesis is and Hill Inhibitory Activity of 2-Cyano-3methylthiobenzyl A crylates[J].Chem, J, Chin, Univ,2005,26(6):1059-1061

[8]高颖,陈晓芳,刘斌,邹小毛,胡方中,杨华铮.2-氰基-3-甲硫基-3-苄氨基丙烯酸取代苯氧乙酯的合成及其除草活性[J].高等学校化学学报,2005,26(6):1059-1061

[9]Jin, L-H.; Zhong, H, M; Song, B.-A.; Hu, D.-Y.; Yang, S.; Liu, G. .Advances in the Synthesis and Biological Activity of 2-Cyanoacrylate[J].Chin. J. Synth. Chem,2005,13(2):113-117

[10]金林红, 钟惠民, 宋宝安, 胡德禹, 杨松, 刘刚.2-氰基丙烯酸酯的合成及生物活性研究进展[J].合成化学,2005,13(2):113-117

[11]Zhang, H, P; Song, B, A; Wang, X, Y; Long, L; Hu, D, Y.; Yang, S.; Xue, W.; Lu, P.; Jin, L,H...Recent Advances in the Synthesis and Biological Activity on Pesticide of α-Cyanoacrylates and Its analognes[J].J, org, chem,2007,28(1):17-28

[12]张慧苹, 宋宝安,王献友, 龙宁, 胡德禹, 杨松, 薛伟, 卢平, 金林红.α-氰基丙烯酸酯及衍其生物的合成与农药生物活性研究进展[J].有机化学,2007,28(1):17-28

[13]Wang, W, Z.; Li, Z, M; Cheng, H, S; Liu, T, Q.; Li, S, Z...Sstudes on Synthesis and Fungicidal Activities of β-Substiuted Phenyl(phnoxyl) Acrylate Esters(amides)[J].Chem, J, Chin, Univ,1999,20(8):1248-1253

[14]王忠文,李正名,陈寒松,刘天麟,李树正.β-取代苯（氧）丙烯酸酯（酰胺）类化合物的合成及其杀菌活性的研究[J].高等学校化学学报,1999,20(8):1248-1253

[15]Yu, S, Y; Li, Z, M.Synthesis of 2-Cyano-3-[(6-Chloro)-3-Pyridylmethyl]-3-Aliphati[J].Chin. J. Pestic. Sci,2002,4(3):79-82

[16]余申义,李正名.2-氰基-3-[(6-氯)-3-吡啶甲基]氨基-3-脂肪氨基丙烯酸乙酯的合成[J].农药学学报,2002,4(3):79-82

[17]Wang, L, G; Wang, F, Y; Cai, Y, M; Li, J, P; wei, P..Synthesis and Fungicidal Activity of Ethyl 2-Cyano-3-substituted Amino-3-(2-methylphenyl)propenoate[J].Chin. J. Org. Chem,2005,25(10):1254-1258

[18]王龙根,王凤云,刁亚梅,倪珏萍,韦萍.2-氰基-3-取代氨基-3-(2-甲基苯基)丙烯酸乙酯的合成和杀菌活性[J].有机化学,2005,25(10):1254-1258

[19]Zhou, J, K; Song, B, A; Hu, D, Y; Xue, W; Jin, L, H.; Lu, P.; Zhou, X.,..Synthesis and bioactivity of Ethyl 2-Cyano-3-Substituted Amino-3-(2-Fluorophenethylamino) Acrylates[J].Chem, J, Onl, Bull,2009,72(1):53-58

[20]周进康, 宋宝安, 胡德禹, 薛伟, 金林红, 卢平, 周霞.2-氰基-3-N-烷氨基-3-(N-2-氟-苯乙氨基)丙烯酸乙酯类化合物的合成及生物活性研究[J].化学通报,2009,72(1):53-58

[21]Song, B ,A; Yang, S, Zhong, H, M, JinL .H ; Hu, D Y; Lin.G .Synthesis and bioactivity of 2-cyanoacrylates containinga trifluoromethylphenyl moiety[J].J Fluorine Chem,2005,126(1):87-92

[22]Zhang, H, P; Song, B, A; Hu, D, Y; Zhong, H, MLin, W, C.; Zhao , S, M..Synthesis of 2-Cyanoacrylates Containing Pyridingl Moiety Under Ultrasound Irradiation[J]..Journal of Heterocyclic Chemistry,2005,42:1211-1214

[23]Wang, LG.; Ni, JP.; Wang, F. Y.; Diao, Y. M.; Wei, P.The Research on Biological Activities of New Fungicide JS399-19[J].Chinese Joumal Pesiticides,2004,43(8):380-383

[24]王龙根, 倪珏萍, 王凤云,刁亚梅,韦萍.新杀菌剂JS399-19的生物活性研究[J].农药,2004,43(8):380-383

[25]Zhang, YB.; Qian, Y, Y.Structure Speciality and Researching Development Survey of Pesticide Containing Fluorine[J].Jiangsu Chemical Industry,2002,30(2):13-15

[26]张一兵, 钱跃言.含氟农药的结构、特性及研究开发概况[J].江苏化工,2002,30(2):13-15

[27]Zhang, GZ.; Yang, YR.; Hao, A. Y. .Researching Development Survey of Pesticide Containing Fluorine, [J].Organo-Fluorine Industry,2004,(2):28-30

[28]张广忠, 杨燕茹, 郝爱友. .含氟农药发展概况[J].有机氟工业,2004,2:28-

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