8-chloro-3-propyl-6,11-dihydro-3H-imidazo[4,5-a]acridin-11-one | 1190604-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-chloro-3-propyl-6,11-dihydro-3H-imidazo[4,5-a]acridin-11-one
• 英文别名: 8-chloro-3-propyl-6H-imidazo[4,5-a]acridin-11-one
• CAS: 1190604-10-4
• 化学式: C₁₇H₁₄ClN₃O
• 分子量: 311.771
• InChiKey: FWOHHIAENQZXHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-chloro-3-propyl-6,11-dihydro-3H-imidazo[4,5-a]acridin-11-one 在 三氯氧磷 作用下， 反应 3.0h， 以80%的产率得到8,11-dichloro-3-propyl-3H-imidazo[4,5-a]acridine
  参考文献：
  名称：

  咪唑并[4,5-a] ac啶酮和咪唑并[4,5-a] ac啶的合成

  摘要：

  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

  DOI：

  10.1007/s00706-009-0109-7
• 作为产物：
  描述：

  8-(4-chlorophenyl)-3-propyl-3H-imidazo[4',5':3,4]benzo[c]isoxazole 在 硫酸 、 sodium nitrite 作用下， 以73%的产率得到8-chloro-3-propyl-6,11-dihydro-3H-imidazo[4,5-a]acridin-11-one
  参考文献：
  名称：

  咪唑并[4,5-a] ac啶酮和咪唑并[4,5-a] ac啶的合成

  摘要：

  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

  DOI：

  10.1007/s00706-009-0109-7

文献信息

• Interactions of human serum albumin with bioactive 3H-imidazo[4,5-a]acridines: Insights from fluorescence spectroscopic studies
  作者：Maryam Rahbari、Mehdi Pordel、Jamshidkhan Chamani

  DOI：10.1134/s1068162016010131

  日期：2016.1

  confirmed by IR, 1H NMR, and mass spectral data. The interactions of 3H-imidazo[4,5-a]acridines with human serum albumin (HSA) were studied by fluorescence spectroscopy. The binding of 3H-imidazo[4,5-a]acridines quenches the HSA fluorescence, revealing a 1: 1 interaction with a binding constant of about 2.34 × 105–3.16 × 106 M–1. A decrease in fluorescence intensity at 339 nm, when excited at 280 nm, is

  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。
• 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.