含（连）氮杂环化合物的合成及生物活性测定
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摘要
为了寻找具有抗白血病活性的新药先导化合物及符合21世纪农药发展要求的新型杀虫剂先导化合物,本文在原有工作基础上采用活性基团叠加法,设计并合成了两个系列共计31个未见文献报道的新化合物。(1)以取代胺和丙烯酸甲酯为起始原料,依次经Michael加成,Dieckmann缩合,水解脱羧及双缩合等多步反应合成了13个未见文献报道S-反式双-N-取代哌啶-4-酮连氮类化合物(Ⅰa~Ⅰm); (2)对已商品化新烟碱类杀虫剂吡虫啉进行结构改造,在保留其药效团新烟碱片段6-氯-3-吡啶基甲基及2-硝基亚胺的基础上,将四氢咪唑环改造为1,3,5-六氢三嗪环并在5号位引入活性基团,设计并合成了18个未见文献报道的1,5-二取代-1,3,5-六氢三嗪-2-硝基亚胺衍生物(Ⅱa~Ⅱr)。目标化合物的结构通式如下:
采用了元素分析、红外光谱(IR)、核磁共振氢谱(1H NMR)、质谱(EI-MS)等方法对上述两个系列的化合物进行了结构表征,并对其物理性质、波谱性质、反应条件、合成方法进行了较为系统的分析和讨论。
为了进一步了解目标化合物Ⅰ的空间结构,初步探索化合物的结构与性质的关系,对化合物(S)-反式双-N-取代哌啶-4-酮连氮(Ⅰb)进行了合成、单晶培养、X-射线衍射晶体结构测定及密度泛函DFT能量计算等研究,对其进行了结构与性质的初步分析。
委托上海师范大学动物细胞-分子生物学实验室,完成了化合物Ⅰa~Ⅰm对白血病K562细胞系增殖影响的测定;同时,委托浙江化工研究院生测部对系列系列(Ⅰ)、(Ⅱ)进行杀虫活性的初步普筛测定,结果表明:系列(Ⅰ)部分化合物对白血病K562细胞系的增殖有明显的抑制作用,系列(Ⅰ)、(Ⅱ)部分化合物分别对朱砂叶螨(Tetranychus cinnabarnus)、东方粘虫(Mythima separate)有较好的选择性杀虫活性。系列(Ⅱ)新烟碱类化合物的杀虫机理通过AutoDock 4.0与昆虫乙酰胆碱受体(nAChR)分子对接模拟得到初步解释。
In order to find some lead compounds with activities of anti-cancer, and search the introduction compounds for new pesticide, obeying the 21st century principle of active-factor-addition, a total of two series of 31 unreported compounds were designed and synthesized. (1) Thirteen unreported novel (S)-trans-N-substitutedpiperidin-4-one azines (Ⅰa~Ⅰm) were synthesized with substituted amines and methyl acrylate as raw materials via a series of Michael addition, Dieckmann condensation, hydrolysis decarhoxylation, condensation reactions. (2) A series of eighteen novel neonicotinoids analogues 1,5-disubstituted- 1,3,5-hexahydrotriazine-2-(N-nitro)imines (Ⅱa~Ⅱr) were designed by modifying the pharmacophore of imidacloprid to 1,3,5-hexahydrotriazine conjugated to nitroimine (=NNO2) to and introducing the phenyl or arylmethyl at the 5-position. The structural formulas of title compounds are as follows respectively:
All these target compounds are new compounds and their structures were confirmed by IR, 1H NMR, MS, and elementary analysis. Their physic-chemical properties, spectrum properties, reaction conditions and synthetic methods were discussed as well.
Further more, in order to investigate the relationship between the structure of compounds (Ⅰ) and its property, we nurtured and obtained the crystal structure (S)-trans-N-benzyl-4-piperidone azine (Ⅰb) by single crystal X-Ray diffraction analysis and took DFT calculations. For these, we had some basic discussion on their structures and activities.
The preliminary biological activities tests of target compounds (Ⅰ)、(Ⅱ) were finished in Branch of National Pesticide R&D South Center. And we Request the Zooblast-molecular biology laboratory of Shanghai Normal University measured the inhibitory rate of the cellular growth of K562 cells using MTT assay for compounds (Ⅰ). The results indicated that some compounds of (Ⅰ) have apoptosis inducing effects on K562 cells; At the same time, we find that few target compounds of (Ⅰ) series have some insecticidal activities to Tetranychus cinnabarnus. Compounds of (Ⅱ) series have some insecticidal activities to Mythima separate. This study also examines the interactions of the most potent analogues with their target nAChR by molecular docking simulation, which explained the structure-activity relationships observed in vitro and may gain insight into their mechanism of action.
采用了元素分析、红外光谱(IR)、核磁共振氢谱(1H NMR)、质谱(EI-MS)等方法对上述两个系列的化合物进行了结构表征,并对其物理性质、波谱性质、反应条件、合成方法进行了较为系统的分析和讨论。
为了进一步了解目标化合物Ⅰ的空间结构,初步探索化合物的结构与性质的关系,对化合物(S)-反式双-N-取代哌啶-4-酮连氮(Ⅰb)进行了合成、单晶培养、X-射线衍射晶体结构测定及密度泛函DFT能量计算等研究,对其进行了结构与性质的初步分析。
委托上海师范大学动物细胞-分子生物学实验室,完成了化合物Ⅰa~Ⅰm对白血病K562细胞系增殖影响的测定;同时,委托浙江化工研究院生测部对系列系列(Ⅰ)、(Ⅱ)进行杀虫活性的初步普筛测定,结果表明:系列(Ⅰ)部分化合物对白血病K562细胞系的增殖有明显的抑制作用,系列(Ⅰ)、(Ⅱ)部分化合物分别对朱砂叶螨(Tetranychus cinnabarnus)、东方粘虫(Mythima separate)有较好的选择性杀虫活性。系列(Ⅱ)新烟碱类化合物的杀虫机理通过AutoDock 4.0与昆虫乙酰胆碱受体(nAChR)分子对接模拟得到初步解释。
In order to find some lead compounds with activities of anti-cancer, and search the introduction compounds for new pesticide, obeying the 21st century principle of active-factor-addition, a total of two series of 31 unreported compounds were designed and synthesized. (1) Thirteen unreported novel (S)-trans-N-substitutedpiperidin-4-one azines (Ⅰa~Ⅰm) were synthesized with substituted amines and methyl acrylate as raw materials via a series of Michael addition, Dieckmann condensation, hydrolysis decarhoxylation, condensation reactions. (2) A series of eighteen novel neonicotinoids analogues 1,5-disubstituted- 1,3,5-hexahydrotriazine-2-(N-nitro)imines (Ⅱa~Ⅱr) were designed by modifying the pharmacophore of imidacloprid to 1,3,5-hexahydrotriazine conjugated to nitroimine (=NNO2) to and introducing the phenyl or arylmethyl at the 5-position. The structural formulas of title compounds are as follows respectively:
All these target compounds are new compounds and their structures were confirmed by IR, 1H NMR, MS, and elementary analysis. Their physic-chemical properties, spectrum properties, reaction conditions and synthetic methods were discussed as well.
Further more, in order to investigate the relationship between the structure of compounds (Ⅰ) and its property, we nurtured and obtained the crystal structure (S)-trans-N-benzyl-4-piperidone azine (Ⅰb) by single crystal X-Ray diffraction analysis and took DFT calculations. For these, we had some basic discussion on their structures and activities.
The preliminary biological activities tests of target compounds (Ⅰ)、(Ⅱ) were finished in Branch of National Pesticide R&D South Center. And we Request the Zooblast-molecular biology laboratory of Shanghai Normal University measured the inhibitory rate of the cellular growth of K562 cells using MTT assay for compounds (Ⅰ). The results indicated that some compounds of (Ⅰ) have apoptosis inducing effects on K562 cells; At the same time, we find that few target compounds of (Ⅰ) series have some insecticidal activities to Tetranychus cinnabarnus. Compounds of (Ⅱ) series have some insecticidal activities to Mythima separate. This study also examines the interactions of the most potent analogues with their target nAChR by molecular docking simulation, which explained the structure-activity relationships observed in vitro and may gain insight into their mechanism of action.
引文
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