indolyl-3-(p-nitrophenylazomethine) | 111601-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: indolyl-3-(p-nitrophenylazomethine)
• 英文别名: (1H-indol-3-ylmethylene)-(4-nitro-phenyl)-amine；N-((indol-1H-3-yl)methylene)-4-nitrobenzenamine；Benzenamine, N-(1H-indol-3-ylmethylene)-4-nitro-；1-(1H-indol-3-yl)-N-(4-nitrophenyl)methanimine
• CAS: 111601-52-6
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: HCEQQBGGYWDSEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 indolyl-3-(p-nitrophenylazomethine) 以 1,4-二氧六环 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  基于吲哚杂环化合物的胶束纳米抗癌药物的简便合成†

  摘要：

  描述了胶束“纳米”吲哚杂环抗癌化合物的简便合成。合成的化合物( 11-23 ) 用UV-VIS、1 H NMR、FT-IR和质谱进行了表征。DNA-化合物加合物的结合能从-20.08 到-23.85 kJ mol -1不等，它们通过疏水相互作用和氢键来稳定。合成的化合物在加合物形成过程中进入 DNA 的小沟。化合物11-23的 DNA 结合常数为 1.00 至 2.00 × 10 5 M -1。记录其胶束形式的载药效率和载药含量。化合物11 , 12 , 1419和19在 670 μL mL -1的胶束浓度下显示出对 HepG2/C3A 系的优异抗癌活性（25-50%）。使用 Lipinski 的“五法则”通过药物相似性预测纳米抗癌药物的效力。总之，化合物11-23可用于治疗癌症。

  DOI：

  10.1039/c8ra07060a
• 作为产物：
  描述：

  吲哚 在 溶剂黄146 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 indolyl-3-(p-nitrophenylazomethine)
  参考文献：
  名称：

  Indole-3-Carbaldehyde 的席夫碱：作为抗菌剂的合成和评价

  摘要：

  摘要 通过吲哚-3-甲醛与不同的芳基胺的缩合反应合成了一系列的吲哚-3-甲醛席夫碱。吲哚-3-甲醛与不同芳基胺的反应是在冰醋酸存在下进行的。用微量分析数据1 H 和13 C NMR、FT-IR 光谱和质谱对所有合成的化合物进行了表征，并筛选了它们对细菌菌株Dickeya和真菌培养尖孢镰刀菌的体外微生物活性。采用琼脂井扩散法。用于细菌和真菌培养的标准分别是多菌灵和庆大霉素。结果表明，合成的席夫碱N -((indol-1 H -3-yl)methylene)-4-nitrobenzenamine 对细菌 (MIC = 2000 µg/mL) 和真菌 (MFC = 5000) 均表现出最大活性。 µg/mL) 培养物与所有其他合成化合物相比。

  DOI：

  10.1134/s1068162022060188

文献信息

• Microwave Assisted Synthesis and Antimicrobial Evaluation of Schiff Bases of Indole-3-aldehyde
  作者：Priyanka Kamaria、N. Kawathekar、Prerna Chaturvedi

  DOI：10.1155/2011/265329

  日期：——

  In order to develop new antimicrobial agents, a series of Schiff bases of indole-3-aldehyde were synthesized by microwave assisted synthesis by takingDMFas solvent and evaluated for their antimicrobial activity. All the synthesized compounds were characterized byIR,¹HNMRand mass spectral analysis. All compounds were tested against five gram positive and five gram negative bacterial strains and one fungal strain. All compounds exhibited better activity against gram positive strains than against gram negative strains and the compounds were found more active againstS.aureusandB.subtilis.

  为了开发新的抗菌剂，通过微波辅助合成合成了一系列吲哚-3-甲醛的席夫碱，以DMF为溶剂，并评估了它们的抗菌活性。所有合成的化合物均通过红外光谱（IR）、质子核磁共振（1H NMR）和质谱分析进行了表征。所有化合物均对五种革兰氏阳性和五种革兰氏阴性细菌菌株以及一种真菌菌株进行了测试。所有化合物对革兰氏阳性菌株的活性优于对革兰氏阴性菌株的活性，而这些化合物对金黄色葡萄球菌（S.aureus）和枯草芽孢杆菌（B.subtilis）的活性更高。
• Synthesis, characterization, structural optimization using density functional theory and superoxide ion scavenging activity of some Schiff bases
  作者：K.K. Upadhyay、Ajit Kumar、Shalini Upadhyay、P.C. Mishra

  DOI：10.1016/j.molstruc.2007.02.031

  日期：2008.2

  Four Schiff bases, 2-[(4-nitro-phenylimino)-methyl]-phenol (NPIMP-2), 4-[(4-nitro-phenylimino)-methyl]-phenol (NPIMP-4), (1H-indol-3-ylmethylene)-(4-nitro-phenyl)-amine (IYNPA), (3-nitro-benzylidene)-(4-nitro-phenyl)-amine (NBNPA) with experimental clue of binding with superoxide ion have been synthesized by the condensation of p-nitroaniline with o-hydroxy benzaldehyde, p-hydroxybenzaldehyde, indole-3-carboxaldehyde and m-nitrobenzaldehyde respectively. These were characterized by IR, H-1 NMR, CHN, mass spectroscopy and UV-visible spectroscopy. The Schiff bases thus synthesized exhibited evidence for their binding with superoxide ion in the form of a high intensity charge transfer band beyond 500 nm in their respective UV-vis spectra on the addition of two drops of N/10 NaOH to their respective 10(-2) M solutions in DMSO. On further addition of two drops of N/10 HCl solution, the charge transfer band vanished and the original spectral pattern of the Schiff bases in DMSO was observed. Out of the four Schiff bases, the binding of NPIMP-4 with O-2(-) was observed to be reversible throughout both the cycles of measurements, but the remaining Schiff bases, namely NPIMP-2, IYNPA and NBNPA were found to show reversibility in only one cycle. The variable temperature 1H NMR (RT-175 degrees C) in DMSO-d(6) revealed reversible intramolecular proton transfer in NPIMP-2 and NPIMP-4 leading to existence of several tautomeric structures. Besides these synthetic and spectroscopic studies, the density functional theory (DFT) calculations were performed for two Schiff bases i.e., NPIMP-2 and NPIMP-4. These calculations provided some important information about the relative stability of various tautomeric forms of NPIMP-2 and NPIMP-4. (c) 2007 Elsevier B.V. All rights reserved.
• Facile synthesis of indole heterocyclic compounds based micellar nano anti-cancer drugs
  作者：Imran Ali、Sofi Danish Mukhtar、Ming Fa Hsieh、Zeid A. Alothman、Abdulrahman Alwarthan

  DOI：10.1039/c8ra07060a

  日期：——

  Facile synthesis of micellar “nano” indole heterocyclic anti-cancer compounds is described. The synthesized compounds (11–23) were characterized by UV-VIS, 1H NMR, FT-IR and mass spectroscopy. The binding energies of DNA–compound adducts varied from −20.08 to −23.85 kJ mol−1, and they were stabilized by hydrophobic interactions and H-bonding. The synthesized compounds enter into minor grooves of DNA

  描述了胶束“纳米”吲哚杂环抗癌化合物的简便合成。合成的化合物( 11-23 ) 用UV-VIS、1 H NMR、FT-IR和质谱进行了表征。DNA-化合物加合物的结合能从-20.08 到-23.85 kJ mol -1不等，它们通过疏水相互作用和氢键来稳定。合成的化合物在加合物形成过程中进入 DNA 的小沟。化合物11-23的 DNA 结合常数为 1.00 至 2.00 × 10 5 M -1。记录其胶束形式的载药效率和载药含量。化合物11 , 12 , 1419和19在 670 μL mL -1的胶束浓度下显示出对 HepG2/C3A 系的优异抗癌活性（25-50%）。使用 Lipinski 的“五法则”通过药物相似性预测纳米抗癌药物的效力。总之，化合物11-23可用于治疗癌症。
• Schiff Bases of Indole-3-Carbaldehyde: Synthesis and Evaluation as Antimicrobial Agents
  作者：B. Priya、D. Utreja、A. Kalia

  DOI：10.1134/s1068162022060188

  日期：2022.12

  Abstract A series of Schiff bases of indole-3-carbaldehyde were synthesized by the condensation reaction of indole-3-carbaldehyde with different aryl amines. The reaction of indole-3-carbaldehyde with different aryl amines was carried out in the presence of glacial acetic acid. All the synthesized compounds were characterized with microanalytical data 1H and 13C NMR, FT-IR spectroscopy and Mass spectrometry

  摘要 通过吲哚-3-甲醛与不同的芳基胺的缩合反应合成了一系列的吲哚-3-甲醛席夫碱。吲哚-3-甲醛与不同芳基胺的反应是在冰醋酸存在下进行的。用微量分析数据1 H 和13 C NMR、FT-IR 光谱和质谱对所有合成的化合物进行了表征，并筛选了它们对细菌菌株Dickeya和真菌培养尖孢镰刀菌的体外微生物活性。采用琼脂井扩散法。用于细菌和真菌培养的标准分别是多菌灵和庆大霉素。结果表明，合成的席夫碱N -((indol-1 H -3-yl)methylene)-4-nitrobenzenamine 对细菌 (MIC = 2000 µg/mL) 和真菌 (MFC = 5000) 均表现出最大活性。 µg/mL) 培养物与所有其他合成化合物相比。