2-(4-methoxy-benzylidenamino)-4-nitro-phenol | 29644-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-methoxy-benzylidenamino)-4-nitro-phenol
• 英文别名: 4-Nitro-2-<4-methoxy-benzylidenamino>-phenol；2-{(E)-[(4-Methoxyphenyl)methylidene]amino}-4-nitrophenol；2-[(4-methoxyphenyl)methylideneamino]-4-nitrophenol
• CAS: 29644-86-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: HFYHMNDCZZTTCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-methoxy-benzylidenamino)-4-nitro-phenol 在 lead(IV) acetate 、 溶剂黄146 作用下， 反应 1.0h， 生成 2-(4-甲氧基苯基)-5-硝基-1,3-苯并恶唑
  参考文献：
  名称：

  苯并咪唑和相关杂环作为拓扑异构酶I毒物的构效关系。

  摘要：

  合成了一系列取代的2-（4-甲氧基苯基）-1H-苯并咪唑类，并作为拓扑异构酶I的抑制剂进行了评估。存在5-甲酰基-，5-（氨基羰基）-或5-硝基（即取代基）能够充当氢键受体的分子）与选择的衍生物抑制拓扑异构酶I的潜力相关。与联苯并咪唑和叔苯并咪唑相反，作为拓扑异构酶I毒物具有活性的取代苯并咪唑显示出最低的DNA亲和力或没有DNA亲和力。5-硝基-2-（4-甲氧基苯基）-1H-苯并咪唑显示出最高的活性，并且比4-硝基位置异构体具有更高的活性。2-（4-甲氧基苯基）苯并恶唑，2-（4-甲氧基苯基）苯并噻唑的5-和6-硝基衍生物 合成了2-（4-甲氧基苯基）吲哚和2-（4-甲氧基苯基）吲哚，它们作为拓扑异构酶I抑制剂的相对活性。这些杂环类似物在DNA和拓扑异构酶I的存在下均不能有效地抑制可裂解复合物的形成，这表明与这些取代的苯并咪唑与酶或酶-DNA复合物的相互作用相关的高度结构特异性。在评估它们

  DOI：

  10.1016/0968-0896(96)00047-8
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 60.0h， 生成 2-(4-methoxy-benzylidenamino)-4-nitro-phenol
  参考文献：
  名称：

  Metallomesogens derived from benzoxazoles–salicylaldimine conjugates

  摘要：

  The synthesis, characterization, and mesomorphic properties of a new series of Schiff bases 2a-h and metal complexes 1a-h-M are prepared and their mesomorphic properties studied. Two single crystallographic structures of 2d (n=12, m=1) and 1g-Pd (n=m=12) were determined by X-ray analysis. Both compounds crystallize in a triclinic space group P-1. A dimeric structure formed by intermolecular H-bonds in 2d was observed, giving nematic phase due to a better aspect ratio. The central geometry at Pd2+ ion is nearly perfect square plane. All Schiff bases 2a-h formed N or/and SmC phases. The formation of mesophases of complexes 1a-h-M was strongly dependent on metal ions incorporated. All Cu2+, Ni2+ and Pd2+ complexes exhibited N or/and SmC phase, respectively. However. Zn2+ and Co2+ complexes were not mesogenic. The lack of mesomorphism was probably attributed to a preferred tetrahedral geometry at Zn2+ and Co2+ over a square-planar geometry at Cu2+ and Pd2+. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.048

文献信息

• Sadekov, I. D.; Maksimenko, A. A.; Mehrotra, G. K., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 594 - 595
  作者：Sadekov, I. D.、Maksimenko, A. A.、Mehrotra, G. K.、Minkin, V. I.

  DOI：——

  日期：——
• Synthesis and antiviral activity of N-2-hydroxyphenylbenzaldimine and N-phenylsalicylaldimine derivatives and their Mn2+-chelates
  作者：N. A. Lagutkin、N. I. Mitin、M. M. Zubairov、V. V. Zelentsov、T. B. Nikolaeva

  DOI：10.1007/bf00758840

  日期：1984.2
• Metallomesogens derived from benzoxazoles–salicylaldimine conjugates
  作者：Chun-Jung Chen、I-Wen Wang、Hwo-Shuenn Sheu、Gene-Hsiang Lee、Chung K. Lai

  DOI：10.1016/j.tet.2011.08.048

  日期：2011.10

  The synthesis, characterization, and mesomorphic properties of a new series of Schiff bases 2a-h and metal complexes 1a-h-M are prepared and their mesomorphic properties studied. Two single crystallographic structures of 2d (n=12, m=1) and 1g-Pd (n=m=12) were determined by X-ray analysis. Both compounds crystallize in a triclinic space group P-1. A dimeric structure formed by intermolecular H-bonds in 2d was observed, giving nematic phase due to a better aspect ratio. The central geometry at Pd2+ ion is nearly perfect square plane. All Schiff bases 2a-h formed N or/and SmC phases. The formation of mesophases of complexes 1a-h-M was strongly dependent on metal ions incorporated. All Cu2+, Ni2+ and Pd2+ complexes exhibited N or/and SmC phase, respectively. However. Zn2+ and Co2+ complexes were not mesogenic. The lack of mesomorphism was probably attributed to a preferred tetrahedral geometry at Zn2+ and Co2+ over a square-planar geometry at Cu2+ and Pd2+. (C) 2011 Elsevier Ltd. All rights reserved.
• Structure-activity relationships of benzimidazoles and related heterocycles as topoisomerase I poisons
  作者：Jung Sun Kim、Qun Sun、Barbara Gatto、Chiang Yu、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/0968-0896(96)00047-8

  日期：1996.4

  the highest activity and was significantly more active than the 4-nitro positional isomer. The 5- and 6-nitro derivatives of 2-(4-methoxyphenyl) benzoxazole, 2-(4-methoxyphenyl)benzothiazole, and 2-(4-methoxyphenyl)indole were synthesized and their relative activity as topoisomerase I inhibitors determined. None of these heterocyclic analogues were effective in significantly inhibiting cleavable-complex

  合成了一系列取代的2-（4-甲氧基苯基）-1H-苯并咪唑类，并作为拓扑异构酶I的抑制剂进行了评估。存在5-甲酰基-，5-（氨基羰基）-或5-硝基（即取代基）能够充当氢键受体的分子）与选择的衍生物抑制拓扑异构酶I的潜力相关。与联苯并咪唑和叔苯并咪唑相反，作为拓扑异构酶I毒物具有活性的取代苯并咪唑显示出最低的DNA亲和力或没有DNA亲和力。5-硝基-2-（4-甲氧基苯基）-1H-苯并咪唑显示出最高的活性，并且比4-硝基位置异构体具有更高的活性。2-（4-甲氧基苯基）苯并恶唑，2-（4-甲氧基苯基）苯并噻唑的5-和6-硝基衍生物 合成了2-（4-甲氧基苯基）吲哚和2-（4-甲氧基苯基）吲哚，它们作为拓扑异构酶I抑制剂的相对活性。这些杂环类似物在DNA和拓扑异构酶I的存在下均不能有效地抑制可裂解复合物的形成，这表明与这些取代的苯并咪唑与酶或酶-DNA复合物的相互作用相关的高度结构特异性。在评估它们