2,2′-((pyridine-2,6-diylbis(methylene))bis((4-((4,5-dimethoxy-2-nitrophenyl)(hydroxy)methyl)phenyl)azanediyl))diacetic acid | 1446476-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2′-((pyridine-2,6-diylbis(methylene))bis((4-((4,5-dimethoxy-2-nitrophenyl)(hydroxy)methyl)phenyl)azanediyl))diacetic acid
• 英文别名: 2-[N-[[6-[[N-(carboxymethyl)-4-[(4,5-dimethoxy-2-nitrophenyl)-hydroxymethyl]anilino]methyl]pyridin-2-yl]methyl]-4-[(4,5-dimethoxy-2-nitrophenyl)-hydroxymethyl]anilino]acetic acid
• CAS: 1446476-01-2
• 化学式: C₄₁H₄₁N₅O₁₄
• 分子量: 827.802
• InChiKey: MJINEKPQDGFKSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  60
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  263
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  2,6-双(溴甲基)吡啶 在 2,6-二甲基吡啶 、 dipotassium hydrogenphosphate 、 三氟甲磺酸三甲基硅酯 、 potassium iodide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 2,2′-((pyridine-2,6-diylbis(methylene))bis((4-((4,5-dimethoxy-2-nitrophenyl)(hydroxy)methyl)phenyl)azanediyl))diacetic acid
  参考文献：
  名称：

  Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺Photocages Using Multiple Nitrobenzyl Groups

  摘要：

  Two generations of DiCast photocages that exhibit light-induced decreases in metal ion affinity have been prepared and characterized. Expansion of the common Zn2+ chelator of N,N-dipicolylaniline (DPA) to include additional aniline ligand provides N,N'-diphenyl-N,N'-bis(pyridin-2-ylmethyl)ethane-1,2-diamine, a tetradentate ligand that was functionalized with two photolabile groups to afford DiCast-1. Uncaging of the nitrobenzhydrol reduces the electron density on two metal bound aniline ligands, which decreases the Zn2+ affinity 190 fold The analogous MonoCast photocage with a single nitrobenzhydrol group only undergoes a 14 fold reduction in affinity after an identical photochemical transformation. A second series of DiCast photocages based on a N,Ni-(pyridine-2,6-diylbis(methylene))dianiline scaffold, which allows the introduction of two additional Zn2+-binding ligands into a preorganized chelator, expand on the multi-photolabile group strategy. DiCast-2 includes two pyridine ligands while DiCast-3 adds two carboxylate groups. Addition of bridging pyridine to the second generation photocages leads to more stable Zn2+ complexes, and photolysis of two photolabile groups increases the Zn2+ affinity changes to 480 fold The Zn2+, Cu2+, and Cd2+ binding properties were examined in all the DiCast photocages and the corresponding photoproducts using UV-vis spectroscopy. Further insight into the photocage Zn2+-binding motifs was obtained by X-ray analysis of DiCast-2 and DiCast-3 model ligands.

  DOI：

  10.1021/ic400465g

文献信息

• Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺Photocages Using Multiple Nitrobenzyl Groups
  作者：Celina Gwizdala、Prem N. Basa、John C. MacDonald、Shawn C. Burdette

  DOI：10.1021/ic400465g

  日期：2013.8.5

  Two generations of DiCast photocages that exhibit light-induced decreases in metal ion affinity have been prepared and characterized. Expansion of the common Zn2+ chelator of N,N-dipicolylaniline (DPA) to include additional aniline ligand provides N,N'-diphenyl-N,N'-bis(pyridin-2-ylmethyl)ethane-1,2-diamine, a tetradentate ligand that was functionalized with two photolabile groups to afford DiCast-1. Uncaging of the nitrobenzhydrol reduces the electron density on two metal bound aniline ligands, which decreases the Zn2+ affinity 190 fold The analogous MonoCast photocage with a single nitrobenzhydrol group only undergoes a 14 fold reduction in affinity after an identical photochemical transformation. A second series of DiCast photocages based on a N,Ni-(pyridine-2,6-diylbis(methylene))dianiline scaffold, which allows the introduction of two additional Zn2+-binding ligands into a preorganized chelator, expand on the multi-photolabile group strategy. DiCast-2 includes two pyridine ligands while DiCast-3 adds two carboxylate groups. Addition of bridging pyridine to the second generation photocages leads to more stable Zn2+ complexes, and photolysis of two photolabile groups increases the Zn2+ affinity changes to 480 fold The Zn2+, Cu2+, and Cd2+ binding properties were examined in all the DiCast photocages and the corresponding photoproducts using UV-vis spectroscopy. Further insight into the photocage Zn2+-binding motifs was obtained by X-ray analysis of DiCast-2 and DiCast-3 model ligands.