4-methoxy-12H-chromeno[2',3':4,5]imidazo-[1,2-a]pyridin-12-one | 1342896-90-5

• 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: 4-methoxy-12H-chromeno[2',3':4,5]imidazo-[1,2-a]pyridin-12-one
• 英文别名: 4-Methoxy-2-oxa-11,17-diazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),3(8),4,6,12,14,16-heptaen-9-one；4-methoxy-2-oxa-11,17-diazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),3(8),4,6,12,14,16-heptaen-9-one
• CAS: 1342896-90-5
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: OCTDEMKOWWOMGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(氰甲基)氯化吡啶 在 N-甲基哌嗪 、 sodium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 3.25h， 生成 4-methoxy-12H-chromeno[2',3':4,5]imidazo-[1,2-a]pyridin-12-one
  参考文献：
  名称：

  某些咪唑并吡啶稠合色酮的选择性合成

  摘要：

  通过一锅法合成了结合有咪唑并[1,2- a ]吡啶和取代的色酮的稠合杂环支架。该反应通过在乙醇中和在DABCO存在下将1-（2-亚氨基-2 H-铬-3-基）吡啶鎓氯化物进行分子内环化而进行。对实验条件的详细研究可以清楚地了解反应途径。

  DOI：

  10.1016/j.tet.2011.09.054

文献信息

• Novel structurally similar chromene derivatives with opposing effects on p53 and apoptosis mechanisms in colorectal HCT116 cancer cells
  作者：Cristovao F. Lima、Marta Costa、M.F. Proença、Cristina Pereira-Wilson

  DOI：10.1016/j.ejps.2015.02.019

  日期：2015.5

  In the present work, novel chromene derivatives fused with the imidazo[1,2-a]pyridine nucleus were tested for their anticancer potential in the human colorectal cancer HCT116 cells. Compounds 2a and 2c showed significant growth inhibitory activity with GI50 of 15 mu M and 11 mu M, respectively. Compound 2c, the most potent, has a carbamate group in position 8 of the pyridine ring, and showed significant cell cycle arrest and induction of cell death by apoptosis, even at 51xM. Besides different potencies, chromene analogs 2a and 2c showed different mechanisms of action. Whereas the carbamate-free chromene 2a induced cell cycle arrest at GI /G0 phase, compound 2c showed to arrest cell cycle at both S and G2 phases. Chromene derivative 2a at concentrations higher than its GI50 remarkably induced caspases-dependent apoptosis in a p53-independent manner. On the other hand, compound 2c increased significantly p53 levels and induced apoptosis in a p53- and caspases-dependent manner, even at concentrations lower than its GI50. Both compounds increased the Bax/Bcl-2 ratio, induced mitochondria depolarization and activated MAP kinases. In conclusion, two novel and structurally similar chromene derivatives showed cytotoxicity to HCT16 cells through opposing effects on p53 levels and apoptosis mechanisms, which may be relevant for further development of drugs acting on distinct molecular targets useful in the treatment of cancers with different genetic profiles and for personalized medicine. (C) 2015 Elsevier B.V. All rights reserved.
• Selective synthesis of some imidazopyridine-fused chromones
  作者：Marta Costa、M. Fernanda Proença

  DOI：10.1016/j.tet.2011.09.054

  日期：2011.11

  A fused heterocyclic scaffold combining the imidazo[1,2-a]pyridine with a substituted chromone was synthesized in a one-pot procedure. The reaction proceeds by intramolecular cyclization of 1-(2-imino-2H-chromen-3-yl)pyridinium chloride in ethanol and in the presence of DABCO. A detailed study of the experimental conditions allowed a clear understanding of the reaction pathway.

  通过一锅法合成了结合有咪唑并[1,2- a ]吡啶和取代的色酮的稠合杂环支架。该反应通过在乙醇中和在DABCO存在下将1-（2-亚氨基-2 H-铬-3-基）吡啶鎓氯化物进行分子内环化而进行。对实验条件的详细研究可以清楚地了解反应途径。