6,7-Dimethoxy-4-[(2-nitroimidazol-1-yl)methyl]chromen-2-one | 133932-25-9

• 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: 6,7-Dimethoxy-4-[(2-nitroimidazol-1-yl)methyl]chromen-2-one
• CAS: 133932-25-9
• 化学式: C₁₅H₁₃N₃O₆
• 分子量: 331.285
• InChiKey: GTNRIJUZFWOXBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-硝基咪唑 、 4-溴甲基-6,7-二甲氧基香豆素 在 sodium methylate 作用下， 生成 6,7-Dimethoxy-4-[(2-nitroimidazol-1-yl)methyl]chromen-2-one
  参考文献：
  名称：

  Fluorescent markers for hypoxic cells: a study of nitroaromatic compounds, with fluorescent heterocyclic side chains, that undergo bioreductive binding

  摘要：

  Several novel compounds having both a 2-nitroimidazole nucleus and a fluorescent ring system in their molecular structure were prepared and evaluated as potential fluorescent probes for hypoxia. Bioreduction of nitroimidazoles, which is inhibited by oxygen, is known to lead to binding of bioreductive metabolites to cellular macromolecules and this provides a mechanism for binding the fluorescent moiety to hypoxic cells. These compounds can incorporate a wide range of fluorophors and can therefore be designed to suit the laser-line wavelengths available for excitation of fluorescence in the flow cytometer. Several nitroimidazoles with naphthalimide side chains were rapidly taken up into cells and became concentrated in the cells, thus reducing their concentration in the extracellular medium. This suggests a potential microscopic bioavailability problem with probes of this type when used in vivo as they would become progressively depleted in the extracellular fluid as they diffused from blood vessels, through layers of packed cells in tumors, to the hypoxic cells where they could undergo hypoxia-specific metabolism. Synthesis of nitroimidazoles with coumarin fluorophors led to several potentially useful probes for hypoxia; substituents on the coumarin fluorophor had a marked effect on the cellular fluorescence of these compounds.

  DOI：

  10.1021/jm00111a049

文献信息

• HODGKISS, RICHARD J.;JONES, GARETH W.;LONG, ANTHONY;MIDDLETON, RICHARD W.+, J. MED. CHEM., 34,(1991) N, C. 2268-2274
  作者：HODGKISS, RICHARD J.、JONES, GARETH W.、LONG, ANTHONY、MIDDLETON, RICHARD W.+

  DOI：——

  日期：——
• Fluorescent markers for hypoxic cells: a study of nitroaromatic compounds, with fluorescent heterocyclic side chains, that undergo bioreductive binding
  作者：Richard J. Hodgkiss、Gareth W. Jones、Anthony Long、Richard W. Middleton、John Parrick、Michael R. L. Stratford、Peter Wardman、George D. Wilson

  DOI：10.1021/jm00111a049

  日期：1991.7

  Several novel compounds having both a 2-nitroimidazole nucleus and a fluorescent ring system in their molecular structure were prepared and evaluated as potential fluorescent probes for hypoxia. Bioreduction of nitroimidazoles, which is inhibited by oxygen, is known to lead to binding of bioreductive metabolites to cellular macromolecules and this provides a mechanism for binding the fluorescent moiety to hypoxic cells. These compounds can incorporate a wide range of fluorophors and can therefore be designed to suit the laser-line wavelengths available for excitation of fluorescence in the flow cytometer. Several nitroimidazoles with naphthalimide side chains were rapidly taken up into cells and became concentrated in the cells, thus reducing their concentration in the extracellular medium. This suggests a potential microscopic bioavailability problem with probes of this type when used in vivo as they would become progressively depleted in the extracellular fluid as they diffused from blood vessels, through layers of packed cells in tumors, to the hypoxic cells where they could undergo hypoxia-specific metabolism. Synthesis of nitroimidazoles with coumarin fluorophors led to several potentially useful probes for hypoxia; substituents on the coumarin fluorophor had a marked effect on the cellular fluorescence of these compounds.