2-((2-(1H-imidazol-4-yl)ethylimino)methyl)-4-nitrophenol | 153469-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-((2-(1H-imidazol-4-yl)ethylimino)methyl)-4-nitrophenol
• 英文别名: 4-(2-(5-nitro-salicylideneimine)ethyl)imidazole；4-{2-((5-Nitrosalicylidene)amino)ethyl}imidazole；2-[2-(1H-imidazol-5-yl)ethyliminomethyl]-4-nitrophenol
• CAS: 153469-62-6
• 化学式: C₁₂H₁₂N₄O₃
• 分子量: 260.252
• InChiKey: JINBSEWWINQCTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  galium(III) nitrate monohydrate 、 2-((2-(1H-imidazol-4-yl)ethylimino)methyl)-4-nitrophenol 以 甲醇 为溶剂， 反应 2.0h， 以16%的产率得到
  参考文献：
  名称：

  N2O供体席夫碱非对称镓（III）配合物的合成，表征和生物学活性

  摘要：

  摘要顺铂及其类似物是一些使用最广泛的抗癌药物。然而，毒性和抗性限制了它们的使用，并且镓化合物由于其显着的抗肿瘤活性和低毒性而成为替代品。在本文中，我们报告了四种新的通式为[Ga（bhi-R）2] +的单核镓（III）配合物，其中bhi-R（R = –NO2，–Br，–Cl和–OCH3）为含咪唑/苯酚的三齿席夫碱的去质子化形式。C1-C4的分子结构通过单晶X射线衍射解析，揭示了单核和同构络合物，金属中心处于扭曲的八面体几何形状。在所有情况下，镓（III）通过咪唑和亚氨基氮原子配位成两个以子午线方式排列的配体分子，和苯酚氧。配合物C1-C4也通过光谱和光谱技术在溶液中表征。进行DFT计算以帮助解释实验结果，并且还可以确定仅获得子午异构体的原因。在24小时内在PBS缓冲液（1％DMSO）中评估了所有复合物的稳定性，结果表明在此期间部分水解。最后，在人肿瘤细胞系MCF-7（乳腺腺癌），A-549（

  DOI：

  10.1016/j.poly.2016.12.020
• 作为产物：
  描述：

  组胺 、 5-硝基水杨醛 以 甲醇 为溶剂， 反应 3.0h， 以71%的产率得到2-((2-(1H-imidazol-4-yl)ethylimino)methyl)-4-nitrophenol
  参考文献：
  名称：

  N2O供体席夫碱非对称镓（III）配合物的合成，表征和生物学活性

  摘要：

  摘要顺铂及其类似物是一些使用最广泛的抗癌药物。然而，毒性和抗性限制了它们的使用，并且镓化合物由于其显着的抗肿瘤活性和低毒性而成为替代品。在本文中，我们报告了四种新的通式为[Ga（bhi-R）2] +的单核镓（III）配合物，其中bhi-R（R = –NO2，–Br，–Cl和–OCH3）为含咪唑/苯酚的三齿席夫碱的去质子化形式。C1-C4的分子结构通过单晶X射线衍射解析，揭示了单核和同构络合物，金属中心处于扭曲的八面体几何形状。在所有情况下，镓（III）通过咪唑和亚氨基氮原子配位成两个以子午线方式排列的配体分子，和苯酚氧。配合物C1-C4也通过光谱和光谱技术在溶液中表征。进行DFT计算以帮助解释实验结果，并且还可以确定仅获得子午异构体的原因。在24小时内在PBS缓冲液（1％DMSO）中评估了所有复合物的稳定性，结果表明在此期间部分水解。最后，在人肿瘤细胞系MCF-7（乳腺腺癌），A-549（

  DOI：

  10.1016/j.poly.2016.12.020

文献信息

• The linear Mn II complex Mn3(5-NO2-salimH)2(OAc)4 provides an alternative structure type for the carboxylate shift in proteins
  作者：Michael J. Baldwin、Jeff W. Kampf、Vincent L. Pecoraro

  DOI：10.1039/c39930001741

  日期：——

  The title complex where 5-NO2-salimH2= 4-[2-(5-NO2-salicylideneimine)ethyl]imidazole} has been structurally characterized and is the first µ-phenolato, µ-carboxylato-O, µ-carboxylato-O,O′ type model for the ‘carboxylate shift’ in polymanganese and polyiron enzymes.

  标题化合物其中5-NO2-salimH2=4-[2-(5- -水杨亚基亚胺)乙基]咪唑}的结构特征已经确定，它是多锰和多铁酶中“羧基转移”的第一个μ-苯酚基、μ-羧基-O、μ-羧基-O,O′型模型。
• Structural and Magnetic Studies of Manganese(II) Complexes of the Imidazole-Containing Ligand 5-NO2-salimH [5-NO2-salimH2 = 4-(2-((5-nitrosalicylidene)amino)ethyl)imidazole] with Varying Nuclearity
  作者：Michael J. Baldwin、Jeff W. Kampf、Martin L. Kirk、Vincent L. Pecoraro

  DOI：10.1021/ic00125a026

  日期：1995.10

  Manganese(II) forms structurally diverse complexes of varying nuclearity with the imidazole-containing Schiff base ligand 5-NO2-salimH(2) [5-NO2-salimH(2) 4-(2-((5-nitrosalicylidene)amino)ethyl)imidazole]. The type of complex formed is determined by the type and stoichiometry of carboxylate added to the reaction mixture. The structures of the complexes Mn(5-NO2-salimH)2, 1, and [Mn(5-NO2-salimH)(mu-HCO2)(CH3OH)](n), 2, have been characterized by X-ray crystallography and are compared to the structure of the linear trinuclear Mn(II) complex Mn-3(5-NO2-salimH)(2)(mu u-CH3CO2)(4), 3, which we reported previously [Baldwin, M. J.; Kampf, J. W.; Pecoraro, V. L. J. Chem. Sec., Chem. Commun. 1993, 1741-1743]. Complex 1 is a mononuclear complex with two meridionally bound ligands. It was crystallized in the orthorhombic space group P2(1)2(1)2(1), with Z = 8, R = 0.0605, and R(w) 0.0590. The unit cell parameters are a 17.170(4) Angstrom, b = 17.811(4) Angstrom, c 18.305(4) Angstrom, and alpha = beta = gamma = 90.000 degrees. Complex 2 is a polymeric chain with equatorial-to-axial formate bridges in the anti-anti configuration, a meridionally bound 5-NO2-salimH in the other equatorial positions, and a methanol ligating in the other axial position. It was crystallized in the orthorhombic space group Pcab (the alternative setting to Pbca), with Z = 8, R = 0.0404, and R(w) = 0.0433. The unit cell parameters are a = 8.070(2) Angstrom, b = 11.895(3) Angstrom, c 34.29(1) Angstrom and alpha = beta = gamma = 90.000 degrees. Complex 3 is a linear trimer with 5-NO2-salimH bound meridionally to each terminal Mn and three bridges from each terminal Mn to the central Mn consisting of the phenolate oxygen of the tridentate ligand, a triatomically bridging acetate, and a monatomically bridging acetate producing a unique (mu-phenolato)(mu-carboxylato-O)(mu-carboxylato-O,O') bridging set which may be of relevance to the carboxylate shift concept. Comparison of the manganese-imidazole bond lengths in these complexes to those of the few 6-coordinate Mn(II)imidazole complexes in the literature provides a range of ''normal'' Mn(II)-imidazole distances for comparison to structurally characterized biological systems and indicates that complexes in which there are multiple bridges to other manganese ions tend to have shorter Mn-N(imidazole) bonds than mononuclear complexes. The variable temperature and variable field magnetic behavior of 2 and 3 were also studied. 2 displays an intrachain exchange interaction J = -0.25 cm(-1). The magnetic behavior of 3 is well modeled with an exchange interaction of J = -1.7 cm(-1) between each terminal manganese and the central manganese, with no coupling between the two terminal manganese ions. The zero-field splitting parameter for 3 is measured from the 4.8 K EPR spectrum as \D\ = 0.19 cm(-1) for the trimeric unit.