2-(5-bromopentyl)-6-amino benzo[de]isoquinoline-1,3-dione | 133932-09-9

• 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: 2-(5-bromopentyl)-6-amino benzo[de]isoquinoline-1,3-dione
• 英文别名: 2-(5-bromopentyl)-6-aminobenzo[de]isoquinoline-1,3-dione；4-amino-N-(5-bromopentyl)-1,8-naphthalimide；6-Amino-2-(5-bromopentyl)benzo[de]isoquinoline-1,3-dione
• CAS: 133932-09-9
• 化学式: C₁₇H₁₇BrN₂O₂
• 分子量: 361.238
• InChiKey: PBZGZJZIHJYBDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  potassium selenocyanate 、 2-(5-bromopentyl)-6-amino benzo[de]isoquinoline-1,3-dione 以 丙酮 为溶剂， 生成 2-(5-delenocyanatopentyl)-6-aminobenzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Naphthalimide based novel organoselenocyanates: Finding less toxic forms of selenium that would retain protective efficacy

  摘要：

  A series of naphthalimide based organoselenocyanates were synthesized and screened for their toxicity as well as their ability to modulate several detoxifying/antioxidative enzyme levels at a primary screening dose of 3 mg/kg b.w. in normal Swiss albino mice for 30 days. Compound 4d showed highest activity in elevating the detoxifying/antioxidant enzymes levels. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.127
• 作为产物：
  描述：

  1,5-二溴戊烷 、 4-氨基-1,8-萘二甲酸酐 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 以69.4%的产率得到2-(5-bromopentyl)-6-amino benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Naphthalimide based novel organoselenocyanates: Finding less toxic forms of selenium that would retain protective efficacy

  摘要：

  A series of naphthalimide based organoselenocyanates were synthesized and screened for their toxicity as well as their ability to modulate several detoxifying/antioxidative enzyme levels at a primary screening dose of 3 mg/kg b.w. in normal Swiss albino mice for 30 days. Compound 4d showed highest activity in elevating the detoxifying/antioxidant enzymes levels. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.127

文献信息

• 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.
• Tunable Solvatochromic Response of Newly Synthesized Antioxidative Naphthalimide Derivatives: Intramolecular Charge Transfer Associated with Hydrogen Bonding Effect
  作者：Sayaree Dhar、Somnath Singha Roy、Dipak Kumar Rana、Sudin Bhattacharya、Sumanta Bhattacharya、Subhash Chandra Bhattacharya

  DOI：10.1021/jp1117773

  日期：2011.3.24

  The solvatochromic behavior of two newly synthesized naphthalimide derivatives (I and II) which have potential antioxidative activities in anticarcinogenic drug development treatment, has been monitored in protic and aprotic solvents of different polarity applying steady-state and time-resolved fluorescence techniques. The compounds exhibit unique photophysical response in different solvent environments. The spectral trends do not appear to originate only from changes in the solvent polarity but also indicate that hydrogen bonding interactions and intramolecular charge transfer (ICT) influence the energy of electronic excitation of the compounds. Incorporation of an amino group at C(4) position of the naphthalimide ring in II makes it behave differently from I in terms of spectral characterization and fluorescence efficacy of the systems. The nonradiative relaxation process of the compounds is governed by medium polarity. The ground state geometry, lowest energy transition, and the UV vis absorption energy of the compounds were studied using density functional theory (DFT) and time-dependent density functional theory (TDDFT) at the B3LYP/6-31G* level, which showed that the calculated outcomes were in good agreement with experimental data.
• 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：——