Citation: 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]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 358-362. doi: 10.6023/cjoc201507029 shu

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

1.
College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029

Corresponding author: Zhang Chenglu,
Received Date: 24 July 2015
Available Online: 8 October 2015
Fund Project: 辽宁省教育厅科学技术研究(No. 2009A426)资助项目 (No. 2009A426)

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.
- Mannich base,
- Cdc25B inhibitor,
- plant growth regulator,
- herbicidal activity
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