4-Amino-3-[(4-amino-2-oxochromen-3-yl)-(4-chlorophenyl)methyl]chromen-2-one | 1478862-51-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-Amino-3-[(4-amino-2-oxochromen-3-yl)-(4-chlorophenyl)methyl]chromen-2-one
• 英文别名: 4-amino-3-[(4-amino-2-oxochromen-3-yl)-(4-chlorophenyl)methyl]chromen-2-one
• CAS: 1478862-51-9
• 化学式: C₂₅H₁₇ClN₂O₄
• 分子量: 444.874
• InChiKey: PHNXRLIEHDASOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

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 13.0h， 生成 4-Amino-3-[(4-amino-2-oxochromen-3-yl)-(4-chlorophenyl)methyl]chromen-2-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

• 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.