3-methyl-6,11-dihydro-3H-imidazo[4,5-a]acridin-11-one | 1190604-07-9

• 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: 3-methyl-6,11-dihydro-3H-imidazo[4,5-a]acridin-11-one
• 英文别名: 3-methyl-6H-imidazo[4,5-a]acridin-11-one
• CAS: 1190604-07-9
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: FCBIYLBVAPPKPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-methyl-6,11-dihydro-3H-imidazo[4,5-a]acridin-11-one 在 三氯氧磷 作用下， 反应 3.0h， 以75%的产率得到11-chloro-3-methyl-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：

  3-methyl-8-phenyl-3H-imidazo[4',5':3,4]benzo[c]isoxazole 在 硫酸 、 sodium nitrite 作用下， 以90%的产率得到3-methyl-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

• 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.
• 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