2-nitrobenzaldehyde hydrazone | 824967-30-8

• 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-nitrobenzaldehyde hydrazone
• 英文别名: (1E)-[(2-Nitrophenyl)methylidene]hydrazine；(E)-(2-nitrophenyl)methylidenehydrazine
• CAS: 824967-30-8
• 化学式: C₇H₇N₃O₂
• 分子量: 165.151
• InChiKey: SDYNELWVLWBQGA-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-nitrobenzaldehyde hydrazone 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 0.08h， 生成 o-nitrobenzyl diazomethane
  参考文献：
  名称：

  Syntheses of Phospholipids Containing 2-Nitrobenzyl Ester Moieties at the Terminals of Alkyl Chains and Properties of Photodegradable Liposomes from the Lipids

  摘要：

  合成了具有2-硝基苯甲酯基团的磷脂1a，该基团作为光分解基团位于烷基链的末端，通过与2-硝基苯基取代的叠氮甲烷反应，从对应的末端羧基含量磷脂2合成。磷脂1b（具有α-甲基-2-硝基苯甲基基团）、1c（具有4,5-二甲氧基-2-硝基苯甲基基团）和1d（具有α-甲基-4,5-二甲氧基-2-硝基苯甲基基团）也同样通过相应的叠氮化合物合成。通过超高压汞灯光分解的磷脂中2-硝基苯甲酯键的光解速率顺序为1b ≥ 1d > 1a > 1c。通过涡旋、超声波和凝胶过滤法制备了含有钙黄绿素的磷脂1a—1d的内水相的脂质体。紫外照射导致被捕获的荧光染料快速释放。释放速率的顺序为：1b ≥ 1d > 1c > 1a，这与光解速率的顺序一致，除了1c，其染料的保持效果较差。

  DOI：

  10.1246/bcsj.71.1923
• 作为产物：
  描述：

  邻硝基苯甲醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到2-nitrobenzaldehyde hydrazone
  参考文献：
  名称：

  Syntheses of Phospholipids Containing 2-Nitrobenzyl Ester Moieties at the Terminals of Alkyl Chains and Properties of Photodegradable Liposomes from the Lipids

  摘要：

  合成了具有2-硝基苯甲酯基团的磷脂1a，该基团作为光分解基团位于烷基链的末端，通过与2-硝基苯基取代的叠氮甲烷反应，从对应的末端羧基含量磷脂2合成。磷脂1b（具有α-甲基-2-硝基苯甲基基团）、1c（具有4,5-二甲氧基-2-硝基苯甲基基团）和1d（具有α-甲基-4,5-二甲氧基-2-硝基苯甲基基团）也同样通过相应的叠氮化合物合成。通过超高压汞灯光分解的磷脂中2-硝基苯甲酯键的光解速率顺序为1b ≥ 1d > 1a > 1c。通过涡旋、超声波和凝胶过滤法制备了含有钙黄绿素的磷脂1a—1d的内水相的脂质体。紫外照射导致被捕获的荧光染料快速释放。释放速率的顺序为：1b ≥ 1d > 1c > 1a，这与光解速率的顺序一致，除了1c，其染料的保持效果较差。

  DOI：

  10.1246/bcsj.71.1923

文献信息

• Supramolecular structures of three isomeric (<i>E</i>,<i>E</i>)-1-(2-iodophenyl)-4-(nitrophenyl)-2,3-diaza-1,3-butadienes: changes in intermolecular interactions consequent upon changes of substituent location
  作者：Christopher Glidewell、John N. Low、Janet M. S. Skakle、James L. Wardell

  DOI：10.1107/s0108270105009248

  日期：2005.5.15

  The supramolecular structures of the three isomeric (E,E)-1-(2-iodophenyl)-4-(2/3/4-nitrophenyl)-2,3-diaza-1,3-butadienes, C14H10IN3O2, are compared. In the 2-nitro isomer, the molecules are disordered across centres of inversion in space group C2/c and are linked into chains by a two-centre iodo-nitro interaction. The molecules of the 3-nitro isomer are linked into a three-dimensional framework by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot I hydrogen bonds and aromatic, pi-pi stacking interactions, while molecules of the 4-nitro isomer are linked into sheets by a C-H center dot center dot center dot O hydrogen bond and a two-centre iodo-nitro interaction.
• EL-MAGHRABY, A. A.;ALY, F. M.;EYADA, H. A., EGYPT. J. PHARM. SCI., 1983, 24, N 1-4, 177-187
  作者：EL-MAGHRABY, A. A.、ALY, F. M.、EYADA, H. A.

  DOI：——

  日期：——
• Syntheses of Phospholipids Containing 2-Nitrobenzyl Ester Moieties at the Terminals of Alkyl Chains and Properties of Photodegradable Liposomes from the Lipids
  作者：Kazuo Yamaguchi、Yoshihiro Tsuda、Taka-aki Shimakage、Akihiro Kusumi

  DOI：10.1246/bcsj.71.1923

  日期：1998.8

  Phospholipid 1a bearing 2-nitrobenzyl ester moieties as a photocleavable group at the terminal of alkyl chains was synthesized from the corresponding terminal carboxy-bearing phospholipid 2 by the reaction with 2-nitrophenyl-substituted diazomethane. Phospholipid, 1b bearing α-methyl-2-nitrobenzyl group, 1c bearing 4,5-dimethoxy-2-nitrobenzyl group, and 1d bearing α-methyl-4,5-dimethoxy-2-nitrobenzyl group were similarly synthesized by the use of the respective diazo compounds. The order of photolysis rates of 2-nitrobenzyl ester linkage of phospholipids by ultrahigh-pressure mercury lamp is 1b ≥ 1d > 1a > 1c. Liposomes of 1a—1d containing calcein in the inner aqueous layer were prepared by vortexing, sonication, and gel-filtration. UV irradiation resulted in fast release of the entrapped fluorescence dye. The order of release rates : 1b ≥ 1d > 1c > 1a is consistent with that of photolysis rates except for 1c, which has poor retention of the dye.

  合成了具有2-硝基苯甲酯基团的磷脂1a，该基团作为光分解基团位于烷基链的末端，通过与2-硝基苯基取代的叠氮甲烷反应，从对应的末端羧基含量磷脂2合成。磷脂1b（具有α-甲基-2-硝基苯甲基基团）、1c（具有4,5-二甲氧基-2-硝基苯甲基基团）和1d（具有α-甲基-4,5-二甲氧基-2-硝基苯甲基基团）也同样通过相应的叠氮化合物合成。通过超高压汞灯光分解的磷脂中2-硝基苯甲酯键的光解速率顺序为1b ≥ 1d > 1a > 1c。通过涡旋、超声波和凝胶过滤法制备了含有钙黄绿素的磷脂1a—1d的内水相的脂质体。紫外照射导致被捕获的荧光染料快速释放。释放速率的顺序为：1b ≥ 1d > 1c > 1a，这与光解速率的顺序一致，除了1c，其染料的保持效果较差。
• Synthesis and biological evaluation of novel (<i>E</i>)-<i>N'</i>-benzylidene hydrazides as novel c-Met inhibitors through fragment based virtual screening
  作者：Jing-wei Liang、Shi-long Li、Shan Wang、Wan-qiu Li、Fan-hao Meng

  DOI：10.1080/14756366.2019.1702655

  日期：2020.1.1

  C-Met plays a crucial role in the development and progression of neoplastic disease. Type II c-Met inhibitors recognise the inactive DFG-out conformation of the kinase, result in better anti-tumour effects due to synergistic effect against the other kinases. According to our previous works, an (E)-N'-benzylidene group was selected as the initial fragment. Two series of (E)-N'-benzylidene hydrazides were designed by fragment growth method. The inhibitory activities were in vitro investigated against c-Met and VEGFR-2. Compound 10b exhibited the most potent inhibitory activity against the c-Met inhibitor (IC50 = 0.37 nM). Compound 11b exhibited multi-target c-Met kinase inhibitory activity as a potential type II c-Met inhibitor (IC50 = 3.41 nM against c-Met; 25.34 nM against VEGFR-2). The two compounds also demonstrate the feasibility of fragment-based virtual screening method for drug discovery.