3-phenyl-1-(p-nitrophenyl)-9-oxa-4-azaphenanthren-10-one | 1478862-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-phenyl-1-(p-nitrophenyl)-9-oxa-4-azaphenanthren-10-one
• 英文别名: 4-(4-Nitrophenyl)-2-phenylchromeno[4,3-b]pyridin-5-one；4-(4-nitrophenyl)-2-phenylchromeno[4,3-b]pyridin-5-one
• CAS: 1478862-43-9
• 化学式: C₂₄H₁₄N₂O₄
• 分子量: 394.386
• InChiKey: SLOVIHRZGLUABB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 3-phenyl-1-(p-nitrophenyl)-9-oxa-4-azaphenanthren-10-one
  参考文献：
  名称：

  New synthetic approach to coumarino[4,3-b]pyridine systems and potential cytotoxic evaluation

  摘要：

  The reaction of 4-aminocoumarin (2) with appropriate alpha,beta-unsaturated ketones gave the corresponding coumarin [4,3-b]pyridines. Thus, treatment of 2 with (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one, (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one, (Z)-ethyl 3-(4-chlorophenyl)-2-cyanoacrylate, and (2E,6E)-2,6-dibenzylidenecyclohexanone (3, 6 and 12) afforded the corresponding coumarino[4,3-b]pyridines 5, 7 and coumarino[4,3-b]quinoline derivatives 13, respectively. Heterocyclic annulations of coumarino [5,4-b]pyridine system were achieved via reaction of 2 (in situ) with benzylidene derivatives of indandione to give 15 which was also obtained by multicomponent condensation reaction of 2 (in situ) with indandione and benzaldehyde. A representative sample of new synthesized compounds was evaluated as cytotoxic agents.

  DOI：

  10.1007/s00044-013-0859-y

文献信息

• Novel 3-phenyl-1- (alkylphenyl)-9-oxa-4-azaphenanthren-10-ones as inhibitors of some enzymes: synthesis, characterization, biological evaluation and molecular docking studies
  作者：Donia Ben Salah、Ahlem Chakchouk-Mtibaa、Lotfi Mellouli、Houcine Ghalla、Waleed Koko、Sadeq M. Al-Hazmy、Lamjed Mansour、Jameel Al-Tamimi、Najet Aouled Dlala、Younes Bouazizi、Khaireddine Dridi、Naceur Hamdi

  DOI：10.1080/07391102.2022.2114938

  日期：——

  -en-1-ones were synthesized and characterized by IR, 1H NMR, 13C spectroscopy and elemental analysis. The synthesized Compounds 5a–f were subjected to molecular docking simulation with three proteins, namely, tyrosyl-tRNA synthetase, heme oxygenase 1 and acetylcholinesterase to evaluate the antibacterial, antioxidant and acetylcholinesterase inhibition, respectively. Moreover, the docked poses of all

   抽象的 合成了一系列新型3-苯基-1-(烷基苯基)-9-氧杂-4-氮杂菲-10-酮和(E)-1-苯基-3-(芳基)丙-2-en-1-酮并通过IR、 1H NMR、 13C光谱和元素分析进行​​表征。将合成的化合物5a-f与酪氨酰-tRNA合成酶、血红素加氧酶1和乙酰胆碱酯酶三种蛋白质进行分子对接模拟，分别评估其抗菌、抗氧化和乙酰胆碱酯酶抑制作用。此外，通过使用MM-GBSA分析计算结合自由能，对蛋白质内部所有化合物的对接姿势进行进一步的动态模拟。化合物5d对抗菌、抗氧化和乙酰胆碱酯酶活性具有高度潜在的抑制作用。化合物3d 、 3f 、 5a和5d在 DPPH 和 ABTS 测定中记录了重要的清除活性。对合成化合物的抗乙酰胆碱酯酶活性的研究表明，化合物5a和3d是最有效的AchE抑制剂，抑制百分比值分别为38%和30%。 拉马斯瓦米·萨尔马 (Ramaswamy H. Sarma) 通讯
• New synthetic approach to coumarino[4,3-b]pyridine systems and potential cytotoxic evaluation
  作者：Wafaa S. Hamama、Mona E. Ibrahim、Asmaa E. Metwalli、Hanafi H. Zoorob

  DOI：10.1007/s00044-013-0859-y

  日期：2014.5

  The reaction of 4-aminocoumarin (2) with appropriate alpha,beta-unsaturated ketones gave the corresponding coumarin [4,3-b]pyridines. Thus, treatment of 2 with (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one, (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one, (Z)-ethyl 3-(4-chlorophenyl)-2-cyanoacrylate, and (2E,6E)-2,6-dibenzylidenecyclohexanone (3, 6 and 12) afforded the corresponding coumarino[4,3-b]pyridines 5, 7 and coumarino[4,3-b]quinoline derivatives 13, respectively. Heterocyclic annulations of coumarino [5,4-b]pyridine system were achieved via reaction of 2 (in situ) with benzylidene derivatives of indandione to give 15 which was also obtained by multicomponent condensation reaction of 2 (in situ) with indandione and benzaldehyde. A representative sample of new synthesized compounds was evaluated as cytotoxic agents.