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

引用本文: 张成路, 唐杰, 殷立莹, 袭焕, 国阳, 孙丽杰. 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[J]. 有机化学, 2016, 36(2): 358-362. doi: 10.6023/cjoc201507029 shu

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

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

1.
辽宁师范大学化学化工学院大连 116029

通讯作者: 张成路

基金项目:
辽宁省教育厅科学技术研究(No. 2009A426)资助项目 (No. 2009A426)

摘要: 将3-对氯苯基、3-对甲氧基苯基和3-正十一烷基-1,2,4-均三唑分别与5个芳香醛反应合成了15个Schiff碱, 然后将Schiff碱、甲醛和吗啉进行多组分一锅反应, 合成14个新型Mannich碱(PCTABM、PMTABM和PUTABM). 为了对比探究3-取代基对分子生物活性的影响, 以3-二茂铁基-1,2,4-均三唑为原料, 利用相似的方法合成了4个3-二茂铁基-1,2,4-均三唑Mannich碱(FcTABM). 应用IR, ¹H NMR和HRMS等对15种新物质进行了结构表征. 评价了目标分子对植物生长调节活性、除草活性和抑制Cdc25B活性. 结果发现, 目标化合物在植物生长调节和除草活性中均表现出优良的活性, 14个目标分子对Cdc25B表现出优良的抑制活性, 其中7c、8e、9e、10b～10e的IC₅₀值低于参照物Na₃VO₄, 有望成为Cdc25B抑制剂.

关键词:

English

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: 张成路

Received Date: 24 July 2015
Available Online: 23 October 2015
Fund Project:
辽宁省教育厅科学技术研究(No. 2009A426)资助项目

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:

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

通讯作者: 张成路

English

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

Corresponding author: 张成路

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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

通讯作者: 张成路

English

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

Corresponding author: 张成路

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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