4-(2-N,N-dimethylamino)ethylamino-N-2-hydroxyethyl-1,8-naphthalimide | 1353887-80-5

• 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: 4-(2-N,N-dimethylamino)ethylamino-N-2-hydroxyethyl-1,8-naphthalimide
• 英文别名: 6-[2-(Dimethylamino)ethylamino]-2-(2-hydroxyethyl)benzo[de]isoquinoline-1,3-dione；6-[2-(dimethylamino)ethylamino]-2-(2-hydroxyethyl)benzo[de]isoquinoline-1,3-dione
• CAS: 1353887-80-5
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: QBBCWJAZJKJUCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[4-(3,3-二苯基丙-2-烯基)哌嗪-1-基]苯甲酸 、 4-(2-N,N-dimethylamino)ethylamino-N-2-hydroxyethyl-1,8-naphthalimide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Novel Naphthalimide-Benzoic Acid Conjugates as Potential Apoptosis-Inducing Agents: Design, Synthesis, and Biological Activity

  摘要：

  A series of novel naphthalimide derivatives with 4‐[4‐(3,3‐diphenylallyl)piperazin‐1‐yl]benzoic acid as side chain were designed and synthesized. Their antitumor activities were evaluated against a variety of cancer cell lines in vitro. Preliminary results showed that most of the derivatives had cytotoxic activity comparable with that of amonafide, with IC50 values of 10−6–10−5 m. Interestingly, compound 12e had the unique antitumor activity against MCF‐7 among the cancer cell lines tested. More importantly, flow cytometric analysis indicated that compared with amonafide, the target compounds could effectively induce G2/M arrest and progress to apoptosis in HL‐60 cells after double staining with annexin V–FITC and propidium iodide. The present work provided a novel class of naphthalimide‐based derivatives with potential apoptosis‐inducing and improved antitumor activity for further optimization.

  DOI：

  10.1111/j.1747-0285.2011.01232.x
• 作为产物：
  描述：

  4-硝基-1,8-萘醛酸酐 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-(2-N,N-dimethylamino)ethylamino-N-2-hydroxyethyl-1,8-naphthalimide
  参考文献：
  名称：

  Novel Naphthalimide-Benzoic Acid Conjugates as Potential Apoptosis-Inducing Agents: Design, Synthesis, and Biological Activity

  摘要：

  A series of novel naphthalimide derivatives with 4‐[4‐(3,3‐diphenylallyl)piperazin‐1‐yl]benzoic acid as side chain were designed and synthesized. Their antitumor activities were evaluated against a variety of cancer cell lines in vitro. Preliminary results showed that most of the derivatives had cytotoxic activity comparable with that of amonafide, with IC50 values of 10−6–10−5 m. Interestingly, compound 12e had the unique antitumor activity against MCF‐7 among the cancer cell lines tested. More importantly, flow cytometric analysis indicated that compared with amonafide, the target compounds could effectively induce G2/M arrest and progress to apoptosis in HL‐60 cells after double staining with annexin V–FITC and propidium iodide. The present work provided a novel class of naphthalimide‐based derivatives with potential apoptosis‐inducing and improved antitumor activity for further optimization.

  DOI：

  10.1111/j.1747-0285.2011.01232.x

文献信息

• Sensor potential of 1,8-naphthalimide and its dyeing ability of cotton fabric
  作者：Desislava Staneva、Ivo Grabchev、Rosica Betcheva

  DOI：10.1016/j.dyepig.2013.01.019

  日期：2013.7

  A new 4-(2-N,N-dimethylamino)ethylamino-N-2-hydroxyethyl-1,8-naphthalimide has been synthesized. The photophysical characteristics have been determined in aqueous and acetonitrile solutions. The influence of metal cations (Ni2+, Zn2+, and Cu-2) and protons on the fluorescence intensity has been studied to evaluate the capacities of the newly synthesized 1,8-naphthalimide as a fluorescence sensor. The 1,8-naphthalimide dye has been chemically bonded to a cotton textile fabric in order to obtain a heterogeneous fluorescent sensor for detecting of metal cations and protons. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel Naphthalimide-Benzoic Acid Conjugates as Potential Apoptosis-Inducing Agents: Design, Synthesis, and Biological Activity
  作者：Aibin Wu、Ping Mei、Yufang Xu、Xuhong Qian

  DOI：10.1111/j.1747-0285.2011.01232.x

  日期：2011.12

  A series of novel naphthalimide derivatives with 4‐[4‐(3,3‐diphenylallyl)piperazin‐1‐yl]benzoic acid as side chain were designed and synthesized. Their antitumor activities were evaluated against a variety of cancer cell lines in vitro. Preliminary results showed that most of the derivatives had cytotoxic activity comparable with that of amonafide, with IC50 values of 10−6–10−5 m. Interestingly, compound 12e had the unique antitumor activity against MCF‐7 among the cancer cell lines tested. More importantly, flow cytometric analysis indicated that compared with amonafide, the target compounds could effectively induce G2/M arrest and progress to apoptosis in HL‐60 cells after double staining with annexin V–FITC and propidium iodide. The present work provided a novel class of naphthalimide‐based derivatives with potential apoptosis‐inducing and improved antitumor activity for further optimization.