N-(2-dimethylamino-ethyl)-4-nitro-1,8-naphthalimide | 88145-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-dimethylamino-ethyl)-4-nitro-1,8-naphthalimide
• 英文别名: N-[2-dimethylamino-ethyl]-4-nitro-1,8-naphthalimide；4-nitro-N-(2-dimethylaminoethyl)-1,8-naphthalimide；N-(2-dimethylaminoethyl)-4-nitro-1,8-naphthalimide；N-[1-dimethylaminoethyl]-4-nitro-1,8-naphthalimide；6-nitro-2-[2-(dimethylamino)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione；1H-Benz(de)isoquinoline-1,3(2H)-dione, 2-(2-(dimethylamino)ethyl)-6-nitro-；2-[2-(dimethylamino)ethyl]-6-nitrobenzo[de]isoquinoline-1,3-dione
• CAS: 88145-14-6
• 化学式: C₁₆H₁₅N₃O₄
• 分子量: 313.313
• InChiKey: VPYVRSPRQFQZFM-UHFFFAOYSA-N

物化性质

• 沸点：
  503.6±40.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-dimethylamino-ethyl)-4-nitro-1,8-naphthalimide 在 锌 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 6-amino-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  氨基酸类双光子荧光染料

  摘要：

  氨基酸类双光子荧光染料，所述荧光染料具有通式I的结构。该类双光子荧光染料在肿瘤活细胞中非核酸区域以及非肿瘤细胞内具有较低的荧光背景，在肿瘤活细胞中核酸区域内具有较强的荧光信号，且对肿瘤活细胞内核酸具有很强的专一性标记。这类化合物具有一定水平的水溶性，同时具有良好的细胞膜通透性。并且还具有较大的有效的双光子吸收截面。本发明的这类化合物同时还具有较低的生物毒性、光毒性、光漂白性。其光谱范围与生物样品的光谱范围有足够大的差异。。

  公开号：

  CN104479396B
• 作为产物：
  描述：

  4-硝基-1,8-萘醛酸酐 、 N,N-二甲基乙二胺 以 甲苯 为溶剂， 反应 48.0h， 以59%的产率得到N-(2-dimethylamino-ethyl)-4-nitro-1,8-naphthalimide
  参考文献：
  名称：

  改变取代基和DNA序列对4-取代的DNA-萘二甲酰亚胺配合物稳定性的影响

  摘要：

  DNA双链体通过许多相互作用而稳定，其中之一是核酸碱基之间的堆叠相互作用。这些相互作用对于设计与DNA结合的小分子很有用。萘二甲酰亚胺嵌入剂已被证明是有价值的抗癌剂，可堆叠在DNA碱基之间并表现出稳定作用。仍然需要设计嵌入剂，它们将表现出这些稳定作用，同时对DNA结合更具选择性。这项工作研究具有不同官能团的4-取代的萘二甲酰亚胺及其与核酸双链体的相互作用。结合的方式通过波长扫描，圆二色性和粘度测量来确定。使用光学熔融实验来测量样品的吸光度随温度的变化。从DNA-嵌入剂复合物得到的Tm值减去从DNA双链体得到的Tm值，得到ΔTm值。ΔTm值表明嵌入剂上的取代基影响DNA-嵌入剂复合物的稳定性。从这项研究的结果以及与先前工作的比较，我们得出结论，核心嵌入剂分子上的取代基类型和位置会影响其与DNA形成的复合物的稳定性。

  DOI：

  10.1016/j.bpc.2018.04.008

文献信息

• 治疗β-地中海贫血和镰状细胞病的方法和组合物
  申请人：中央研究院

  公开号：CN105492428A

  公开（公告）日：2016-04-13

  治疗贫血(如β-地中海贫血和镰状性细胞贫血)的化合物、药物组合物和方法。
• METHODS AND COMPOSITIONS FOR TREATING BETA-THALASSEMIA AND SICKLE CELL DISEASE
  申请人：ACADEMIA SINICA

  公开号：US20160106728A1

  公开（公告）日：2016-04-21

  Compounds, pharmaceutical compositions, and methods for treating anemia β-thalassemia anemia or sickle cell anemia.

  化合物、药物组合和治疗贫血β-地中海贫血或镰状细胞贫血的方法。
• Selenium-containing naphthalimides as anticancer agents: Design, synthesis and bioactivity
  作者：Liwei Zhao、Jianfeng Li、Yiquan Li、Jianwen Liu、Thomas Wirth、Zhong Li

  DOI：10.1016/j.bmc.2012.02.049

  日期：2012.4

  Selenium analogues (4b-4h, and 4j) of two known sulfur compounds were synthesized and tested their anticancer activities. The selenium compound 4b had comparable activity with its sulfur analogue 4a, while DNA-binding study showed these two compounds had similar interaction with ct-DNA, the K-b was 8.23 and 2.36, respectively. The primary results showed that most compounds had moderate anticancer activities with IC50 values between 10 (6) and 10 (5) M. Another selenium analogue 4j showed the highest activity with the IC50 values around 5.3 mu M against K562 and MCF-7 cell lines. More importantly, the organochalcogen compounds exhibited stronger anticancer activities against K562 cell line than the other cell lines tested. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• Facile synthesis, sensor activity and logic behaviour of 4-aryloxy substituted 1,8-naphthalimide
  作者：Nevena V. Marinova、Nikolai I. Georgiev、Vladimir B. Bojinov

  DOI：10.1016/j.jphotochem.2013.01.008

  日期：2013.2

  A series of 4-phenoxy- and 4-alkoxy-1,8-naphthalimide fluorophores have been synthesized in high yields at room temperature applying novel facile synthesis. One of the compounds was designed as a fluorescent PET sensor according to the "fluorophore-spacer-receptor" model. The ability of this molecule to detect protons and transition metal cations with pronounced selectivity towards Fe3+ was demonstrated. Moreover the 4-phenoxy substituted 1,8-naphthalimides were highly solvent sensitive and able to detect small quantities of water. The potential of the 1,8-naphthalimide sensor to execute INHIBIT logic function at molecular level was also demonstrated. (C) 2013 Elsevier B.V. All rights reserved.
• 4-Amino-1,8-naphthalimide-Based Tröger’s Bases As High Affinity DNA Targeting Fluorescent Supramolecular Scaffolds
  作者：Emma B. Veale、Daniel O. Frimannsson、Mark Lawler、Thorfinnur Gunnlaugsson

  DOI：10.1021/ol9013602

  日期：2009.9.17

  The synthesis and photophysical and biological Investigation of fluorescent 1,8-naphthalimide conjugated Troger's bases 1-3 are described. These structures bind strongly to DNA in competitive media at pH 7.4, with concomitant modulation in their fluorescence emission. These structures also undergo rapid cellular uptake, being localized within the nucleus within a few hours, and are cytotoxic against HL60 and (chronic myeloid leukemia) K562 cell lines.