Synthesis and Inhibitory Activity of Novel Ferrocenyl 1,2,4-Triazole Mannich Bases

doi:10.6023/cjoc201405015

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2331-2337.DOI: 10.6023/cjoc201405015 Previous Articles Next Articles

Notes

新型二茂铁基1,2,4-三唑Mannich碱的合成及其Cdc25B抑制活性

张成路, 王雪, 国阳, 吴一非, 高丽娜, 孙丽杰,柴金华, 朱长安

辽宁省生物与制药重点实验室辽宁师范大学化学化工学院大连 116029

收稿日期:2014-05-10 修回日期:2014-07-14 发布日期:2014-07-17
通讯作者: 张成路,zhangchenglu@lnnu.edu.cn E-mail:zhangchenglu@lnnu.edu.cn
基金资助:
辽宁省教育厅科学技术(No.2009A426)资助项目.

Synthesis and Inhibitory Activity of Novel Ferrocenyl 1,2,4-Triazole Mannich Bases

Zhang Chenglu, Wang Xue, Guo Yang, Wu Yifei, Gao Lina, Sun Lijie, Chai Jinhua, Zhu Chang'an

Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029

Received:2014-05-10 Revised:2014-07-14 Published:2014-07-17
Supported by:
Project supported by the Technology Research Program of Liaoning Provincial Department of Education (No.2009A426).

15 novel 3-ferrocenyl-1,2,4-triazole Mannich bases (3a~3e, 4a~4e and 5a~5e) were designed and synthesized for the first time by Mannich reaction from five 3-ferrocenyl-1,2,4-triazole Schiff bases, which reacted with morpholine, 1-methylpiperazine and piperazine, respectively. The structures of 3, 4 and 5 were characterized by IR, ¹H NMR and HRMS. The X-ray single crystal diffraction of 3b was obtained. The results showed that the target compounds were successfully synthesized. The target products were evaluated for their Cdc25B inhibitory activities. The test results indicated that 13 of 15 Mannich bases exhibited good inhibitory activity, wherein IC₅₀ values of 3c, 4a, 5b, 5c and 5e were lower than the positive control compound Na₃VO₄ (1.86±0.24 μg·mL^-¹) with 0.91±0.18, 0.62±0.13, 1.10±0.33, 0.44±0.04 and 0.67±0.13 μg·mL^-¹, respectively. Compared with PTP1B inhibition activity results, the target products have a selective inhibitory effect on Cdc25B.

Key words: ferrocene, 1,2,4-triazole, Mannich base, Cdc25B inhibitor

Cite this article

Zhang Chenglu, Wang Xue, Guo Yang, Wu Yifei, Gao Lina, Sun Lijie, Chai Jinhua, Zhu Chang'an. Synthesis and Inhibitory Activity of Novel Ferrocenyl 1,2,4-Triazole Mannich Bases[J]. Chin. J. Org. Chem., 2014, 34(11): 2331-2337.

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新型二茂铁基1,2,4-三唑Mannich碱的合成及其Cdc25B抑制活性

Synthesis and Inhibitory Activity of Novel Ferrocenyl 1,2,4-Triazole Mannich Bases

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