N-(3-bromopropyl)-4-amino-1,8-naphthalimide | 107107-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(3-bromopropyl)-4-amino-1,8-naphthalimide
• 英文别名: 4-amino-N-(3-bromopropyl)naphthalimide；6-Amino-2-(3-bromopropyl)benzo[de]isoquinoline-1,3-dione
• CAS: 107107-83-5
• 化学式: C₁₅H₁₃BrN₂O₂
• 分子量: 333.184
• InChiKey: VXKUMMJJLYSYJC-UHFFFAOYSA-N

物化性质

• 沸点：
  532.4±40.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-bromopropyl)-4-amino-1,8-naphthalimide 在 sodium methylate 、 氯乙酸 作用下， 反应 1.25h， 生成 4-(chloroacetamido)-N-<3-(2-nitroimidazol-1-yl)propyl>-1,8-naphthalimide
  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
• 作为产物：
  描述：

  4-氨基-1,8-萘胺 、 1,3-二溴丙烷 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3-bromopropyl)-4-amino-1,8-naphthalimide
  参考文献：
  名称：

  Synthesis and fluorescence properties of naphthalimide-containing Tröger’s bases

  摘要：

  Troger's bases based on the naphthalimide fluorophore have been prepared from N-alkyl-4-amino-1,8-naphthalimides. The fluorescence emission intensity of these dyes is highly medium dependent. In cyclohexane, these dyes emit near 440 nm with high quantum yields, addition of cosolvents reduces the fluorescence intensity near 440 mn and leads to increased fluorescence intensity around 480 nm. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.01.166

文献信息

• Synthesis and fluorescence of<i>N</i>-substituted-1,8-naphthalimides
  作者：Richard W. Middleton、John Parrick、Eric D. Clarke、Peter Wardman

  DOI：10.1002/jhet.5570230337

  日期：1986.5

  AbstractA number of novel N‐substituted‐1,8‐naphthalimides have been prepared and their fluorescence yields measured in water at pH 7.4. The type of substitutent and the substitution pattern on the naphthalimide nucleus produce markedly different fluorescence yields, (quantum efficiencies, ø varying from ø = 0‐0037 for N‐(3‐N'‐morpholino‐1‐propyl)‐4‐amino‐3‐methoxy‐1,8‐naphthalirnide (7) to ø = 0–77 for N‐(3‐bromopropyl)‐4‐acetamido‐1,8‐naphthalimide (31).
• 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：——
• Synthesis and fluorescence properties of naphthalimide-containing Tröger’s bases
  作者：Nicholas R. Deprez、Kristy A. McNitt、Matthew E. Petersen、Robert G. Brown、David E. Lewis

  DOI：10.1016/j.tetlet.2005.01.166

  日期：2005.3

  Troger's bases based on the naphthalimide fluorophore have been prepared from N-alkyl-4-amino-1,8-naphthalimides. The fluorescence emission intensity of these dyes is highly medium dependent. In cyclohexane, these dyes emit near 440 nm with high quantum yields, addition of cosolvents reduces the fluorescence intensity near 440 mn and leads to increased fluorescence intensity around 480 nm. (C) 2005 Published by Elsevier Ltd.
• 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.