Synthesis and Bioactivities of Novel N-1,2,4-Triazole Moieties Imines Containing Fluorocinnamylidene

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (04): 569-575. Previous Articles Next Articles

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N-(1,2,4-三唑)含氟肉桂醛亚胺的合成及生物活性

李黔柱^a,b 宋宝安^*,a 蔡学建^a 郑玉国^a 郭晴晴^a

(a贵州大学精细化工研究开发中心教育部绿色农药和农业生物工程重点实验室贵阳 550025)
(b毕节学院化学系毕节 551700)

收稿日期:2009-02-25 修回日期:2009-10-20 发布日期:2009-12-02

Synthesis and Bioactivities of Novel N-1,2,4-Triazole Moieties Imines Containing Fluorocinnamylidene

Li, Qianzhu ^a,b Song, Baoan ^*,a Cai, Xuejian^a Zheng, Yuguo^a Guo, Qingqing^a

(a Key Laboratory of Green Pesticide and Bioengineering, Ministry of Educational, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025)
(b Department of Chemistry, Bijie University, Bijie 551700)

Received:2009-02-25 Revised:2009-10-20 Published:2009-12-02

Abstract

A series of 4-(substituted-3-phenylallylideneamino)-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-tria- zole-5(4H)-thione (3) were synthesized by condensation reaction of 4-amino-3-(3,4,5-trimethoxyphenyl)- 1H-1,2,4-triazole-5(4H)-thione (2) with various fluorocinnamaldehydes. Alkylation of 3 with alkyl halides affordedN-1,2,4-triazole moieties imines containing fluorocinnamylidene 4. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and elemental analyses. The single crystal structure of compound 4g was determined by X-ray diffraction analysis, which revealed that the two double bonds N＝C and C＝Coutside the rings were of E,E-configurations. The preliminary bioassay showed that some of them exhibited moderate antiviral activity.

Key words: fluorocinnamaldehyde, 1,2,4-triazole, imines, crystal structure, bioactivity

Cite this article

LI Qian-Zhu, SONG Bao-An, CAI Xue-Jian, ZHENG Yu-Guo, GUO Qing-Qing. Synthesis and Bioactivities of Novel N-1,2,4-Triazole Moieties Imines Containing Fluorocinnamylidene[J]. Chin. J. Org. Chem., 2010, 30(04): 569-575.

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N-(1,2,4-三唑)含氟肉桂醛亚胺的合成及生物活性

Synthesis and Bioactivities of Novel N-1,2,4-Triazole Moieties Imines Containing Fluorocinnamylidene

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