3-butyl-8-phenyl -3H-imidazo[4',5':3,4]benzo[1,2-c]isoxazole | 1190604-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-butyl-8-phenyl -3H-imidazo[4',5':3,4]benzo[1,2-c]isoxazole
• 英文别名: 3-Butyl-8-phenyl-3h-imidazo[4',5':3,4]benzo[c]isoxazole；3-butyl-8-phenylimidazo[4,5-e][2,1]benzoxazole
• CAS: 1190604-05-7
• 化学式: C₁₈H₁₇N₃O
• 分子量: 291.352
• InChiKey: YVXFBCIVLMEXMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-butyl-8-phenyl -3H-imidazo[4',5':3,4]benzo[1,2-c]isoxazole 在 硫酸 、 sodium nitrite 、 三氯氧磷 作用下， 反应 8.0h， 生成 3-butyl-11-chloro-3H-imidazo[4,5-a]acridine
  参考文献：
  名称：

  人血清白蛋白与生物活性 3H-咪唑并[4,5-a]吖啶的相互作用：荧光光谱研究的见解

  摘要：

  通过咪唑并[4,5-a]吖啶酮在沸腾的POCl3中反应，可以方便地合成几种3H-咪唑并[4,5-a]吖啶衍生物。咪唑并吖啶酮通过 3H-咪唑并[4',5':3,4]苯并[c]异恶唑在含有亚硝酸的浓硫酸中在室温下重排获得。所有新合成化合物的结构均通过 IR、1H NMR 和质谱数据确认。通过荧光光谱研究了 3H-咪唑并[4,5-a]吖啶与人血清白蛋白 (HSA) 的相互作用。3H-咪唑并[4,5-a]吖啶的结合淬灭了 HSA 荧光，显示出 1:1 的相互作用，结合常数约为 2.34 × 105–3.16 × 106 M–1。当在 280 nm 激发时，339 nm 处的荧光强度降低，归因于配体的存在引起的蛋白质荧光团环境的变化。3H-咪唑并[4,5-a]吖啶与HSA相互作用的差异使用荧光分光光度法技术观察。

  DOI：

  10.1134/s1068162016010131
• 作为产物：
  描述：

  6-硝基苯并咪唑 在 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 3-butyl-8-phenyl -3H-imidazo[4',5':3,4]benzo[1,2-c]isoxazole
  参考文献：
  名称：

  人血清白蛋白与生物活性 3H-咪唑并[4,5-a]吖啶的相互作用：荧光光谱研究的见解

  摘要：

  通过咪唑并[4,5-a]吖啶酮在沸腾的POCl3中反应，可以方便地合成几种3H-咪唑并[4,5-a]吖啶衍生物。咪唑并吖啶酮通过 3H-咪唑并[4',5':3,4]苯并[c]异恶唑在含有亚硝酸的浓硫酸中在室温下重排获得。所有新合成化合物的结构均通过 IR、1H NMR 和质谱数据确认。通过荧光光谱研究了 3H-咪唑并[4,5-a]吖啶与人血清白蛋白 (HSA) 的相互作用。3H-咪唑并[4,5-a]吖啶的结合淬灭了 HSA 荧光，显示出 1:1 的相互作用，结合常数约为 2.34 × 105–3.16 × 106 M–1。当在 280 nm 激发时，339 nm 处的荧光强度降低，归因于配体的存在引起的蛋白质荧光团环境的变化。3H-咪唑并[4,5-a]吖啶与HSA相互作用的差异使用荧光分光光度法技术观察。

  DOI：

  10.1134/s1068162016010131

文献信息

• Synthesis of imidazo[4,5-a]acridones and imidazo[4,5-a]acridines as potential antibacterial agents
  作者：Mohammad Rahimizadeh、Mehdi Pordel、Mehdi Bakavoli、Zahra Bakhtiarpoor、Ala Orafaie

  DOI：10.1007/s00706-009-0109-7

  日期：2009.6

  AbstractNew imidazo[4,5-a]acridone derivatives were synthesized from the rearrangement of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles. New imidazo[4,5-a]acridines were obtained from the reaction of imidazo[4,5-a]acridones in boiling POCl3. All of these compounds exhibited antimicrobial activities comparable to streptomycin as reference drug. Graphical abstract

  摘要从3 H-咪唑并[4'，5'：3,4]苯并[ c ]异恶唑的重排反应合成了新的咪唑并[4,5- a ] ac啶酮衍生物。新咪唑并[4,5一]吖啶从咪唑的反应[4,5-获得一个]吖啶酮在沸腾的POCl 3。所有这些化合物均显示出与链霉素作为参考药物相当的抗菌活性。 图形概要
• Synthesis, Characterization, and DFT Calculations of New Fluorescent Cu(II) Complexes of Heterocyclic Ligands
  作者：S. Rastegarnia、M. Pordel、S. Allameh

  DOI：10.1134/s0022476619020082

  日期：2019.2

  established by spectral, analytical data and Job’s method. To gain insight into the geometry and spectral properties of the Cu(II) complexes, DFT calculations are performed at the B3LYP/6-311++G(d,p) level. The DFT-calculated spectral properties are in good agreement with the experimental values, confirming the suitability of the optimized geometries for the copper complexes. The photophysical properties of the

  报道了两种新的从苯并咪唑衍生的荧光杂环配体的铜 (II) 配合物的合成、光谱研究和量子化学研究。荧光杂环配体是通过还原咪唑并[4',5':3,4]苯并[1,2-c]异恶唑衍生物合成的，并通过元素分析、红外、质谱和核磁共振光谱进行表征。二齿配体与 Cu(II) 阳离子的配位产生橙色配合物。配合物的结构是通过光谱、分析数据和 Job 方法建立的。为了深入了解 Cu(II) 配合物的几何形状和光谱特性，在 B3LYP/6-311++G(d,p) 级别进行 DFT 计算。DFT 计算的光谱特性与实验值非常吻合，确认优化几何形状对铜配合物的适用性。配体和 Cu(II) 配合物的光物理性质通过紫外-可见光和荧光光谱表征。从配体 p 轨道到 Cu(II) d 轨道的有效电荷转移可能被认为是复合物颜色的主要原因。
• Synthesis, antiviral, and cytotoxic investigation of imidazo[4,5-a]acridones
  作者：Leila Rezaei Daghigh、Mehdi Pordel、Abolghasem Davoodnia、Maryam Jajarmi

  DOI：10.1007/s00044-015-1438-1

  日期：2015.11

  The importance of virus infections and the early successes with some antiviral drugs have prompted the search for new agents, and it has been focused on compounds that are active against herpesviruses, retroviruses, and rhinoviruses. In this paper, 3H-imidazo[4,5-a]acridones are introduced as new antiviral agents against a panel of DNA and RNA viruses, including herpes simplex virus-1 (KOS), herpes simplex virus-2 (G), vaccinia virus, vesicular stomatitis virus, and herpes simplex virus-1 TK-KOS ACV (r). Also, these compounds were cytostatic in the higher micromolar range. 3H-imidazo[4,5-a]acridones were synthesized by Tanasescu reaction of 3H-imidazo[4',5':3,4]benzo [c]isoxazoles in concentrated sulfuric acid containing nitrous acid in excellent yields. The advanced compounds were obtained from the reaction of N-alkyl-5-nitrobenzimidazoles with different aryl acetonitriles under basic conditions. Structures of all newly synthesized compounds were confirmed by IR, H-1 NMR, and mass spectral data. The results indicated that the title compounds have mild-to-potent activities in comparison with their appropriate reference standards.
• New fluorescent 3H-imidazo[4,5-e][2,1]benzoxazoles: synthesis, spectroscopic characterization, and antibacterial activity
  作者：Mitra Rezazadeh、Mehdi Pordel、Abolghasem Davoodnia、Sattar Saberi

  DOI：10.1007/s10593-015-1796-0

  日期：2015.10

  The new fluorophores of the 3H-imidazo[4,5-e][2,1]benzoxazoles series were synthesized by the regioselective nitration of 3-alkyl-8-phenyl-3H-imidazo[4,5-e][2,1]benzoxazoles. The latter compounds were obtained from the reaction of 1-alkyl-5-nitro-1H-benzimidazoles with benzyl cyanide in basic MeOH solution. The structures of synthesized compounds were established using spectral (UV-vis, IR, H-1 NMR, C-13 NMR, and NOESY) and analytical data. Furthermore, it was found that these fluorophores underwent thermal rearrangement to new 5H-imidazo[4,5-f][2,1,3]benzoxadiazole 3-oxides in AcOH in moderate yields. The fluorescence properties and antibacterial activities of new compounds against Gram-positive and Gram-negative bacterial species were also studied.
• Alikhani, Elaheh; Pordel, Mehdi; Beyramabadi, Safar Ali, Indian Journal of Heterocyclic Chemistry, 2019, vol. 29, # 4, p. 311 - 318
  作者：Alikhani, Elaheh、Pordel, Mehdi、Beyramabadi, Safar Ali

  DOI：——

  日期：——