One Pot Synthesis of 3-Substituted-1-morpholino-1,2,4-triazole Mannich Bases and Their Activity Evaluation

doi:10.6023/cjoc201507029

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 358-362.DOI: 10.6023/cjoc201507029 Previous Articles Next Articles

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一锅法合成3-取代-1-吗啉基-1,2,4-均三唑Mannich碱及其活性评价

张成路, 唐杰, 殷立莹, 袭焕, 国阳, 孙丽杰

辽宁师范大学化学化工学院大连 116029

收稿日期:2015-07-24 修回日期:2015-10-08 发布日期:2015-10-23
通讯作者: 张成路 E-mail:zhangchenglu@lnnu.edu.cn
基金资助:
辽宁省教育厅科学技术研究(No. 2009A426)资助项目

One Pot Synthesis of 3-Substituted-1-morpholino-1,2,4-triazole Mannich Bases and Their Activity Evaluation

Zhang Chenglu, Tang Jie, Yin Liying, Xi Huan, Guo Yang, Sun Lijie

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029

Received:2015-07-24 Revised:2015-10-08 Published:2015-10-23
Supported by:
Project supported by the Science and Technology Research Program of Liaoning Provincial Department of Education (No. 2009A426).

1. One Pot Synthesis of 3-Substituted-1-morpholino-1,2,4-triazole Mannich Bases and Their Activity Evaluation.PDF(7803KB)

Abstract

15 Schiff bases were synthesized by the reactions of 3-p-chlorophenyl, 3-p-methoxyphenyl and 3-n-pentyl-1,2,4-triazole with five different aromatic aldehydes, respectively. Then 14 novel Mannich bases (PCTABM, PMTABM and PETABM) were first afforded by the reactions of Schiff bases with formaldehyde and morpholine through multi-component one-pot reaction. In order to explore the effect of different 3-substituted groups on biological activities, four Mannich bases FcTABM of 3-ferrocenyl-1,2,4-triazole were also synthesized starting from 3-ferrocenyl-1,2,4-triazole by the similar method. IR, ¹H NMR and HRMS were used to characterize the structure of the target molecules. The biological activities of the target molecules were evaluated. As a result, the target compounds exhibited excellent activities in plant growth regulators and herbicidal activity. There are 14 target compounds exhibited excellent inhibitory activity against Cdc25B, in which the IC₅₀ values of 7c, 8e, 9e, 10b～10e IC₅₀ were all smaller than the reference Na₃VO₄, which were expected to be Cdc25B inhibitors.

Key words: Mannich base, Cdc25B inhibitor, plant growth regulator, herbicidal activity

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Zhang Chenglu, Tang Jie, Yin Liying, Xi Huan, Guo Yang, Sun Lijie. One Pot Synthesis of 3-Substituted-1-morpholino-1,2,4-triazole Mannich Bases and Their Activity Evaluation[J]. Chin. J. Org. Chem., 2016, 36(2): 358-362.

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一锅法合成3-取代-1-吗啉基-1,2,4-均三唑Mannich碱及其活性评价

One Pot Synthesis of 3-Substituted-1-morpholino-1,2,4-triazole Mannich Bases and Their Activity Evaluation

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