4-(dimethylamino)-N-(9-nitroanthracen-2-yl)butanamide | 943019-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-(dimethylamino)-N-(9-nitroanthracen-2-yl)butanamide
• CAS: 943019-58-7
• 化学式: C₂₀H₂₁N₃O₃
• 分子量: 351.405
• InChiKey: LLRAYIZQGMSOIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)-N-(9-nitroanthracen-2-yl)butanamide 以 丙酮 、 苯 为溶剂， 反应 3.0h， 以77%的产率得到4-(dimethylamino)-N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)butanamide
  参考文献：
  名称：

  9-Nitroanthracene derivative as a precursor of anthraquinone for photodynamic therapy

  摘要：

  Anthraquinones are typical photosensitizers used in photodynamic therapy (PDT). However, systemic toxicity is a major problem for anthraquinones due to their ability not only to bind DNA but also to cause oxidative stress even without photoirradiation. To avoid such disadvantages in cancer therapy, we designed and synthesized a novel 9-nitroanthracene derivative (1) as a precursor of anthraquinone. Under photoirradiation, I is converted into anthraquinone via generation of nitric oxide as confirmed by ESR. Strong DNA cleavage specifically at guanine under photoirradiation was also observed, characteristic of DNA-cleaving reactions by photoirradiated anthraquinones. We propose development of I as an alternative approach toward PDT that reduces the systemic toxicity of anthraquinone. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.029
• 作为产物：
  描述：

  2-氨基蒽 在 N-甲基吗啉 、 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-(dimethylamino)-N-(9-nitroanthracen-2-yl)butanamide
  参考文献：
  名称：

  9-Nitroanthracene derivative as a precursor of anthraquinone for photodynamic therapy

  摘要：

  Anthraquinones are typical photosensitizers used in photodynamic therapy (PDT). However, systemic toxicity is a major problem for anthraquinones due to their ability not only to bind DNA but also to cause oxidative stress even without photoirradiation. To avoid such disadvantages in cancer therapy, we designed and synthesized a novel 9-nitroanthracene derivative (1) as a precursor of anthraquinone. Under photoirradiation, I is converted into anthraquinone via generation of nitric oxide as confirmed by ESR. Strong DNA cleavage specifically at guanine under photoirradiation was also observed, characteristic of DNA-cleaving reactions by photoirradiated anthraquinones. We propose development of I as an alternative approach toward PDT that reduces the systemic toxicity of anthraquinone. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.029

文献信息

• 9-Nitroanthracene derivative as a precursor of anthraquinone for photodynamic therapy
  作者：Kiyoshi Fukuhara、Shinji Oikawa、Nana Hakoda、Yasunori Sakai、Yusuke Hiraku、Takuji Shoda、Shinichi Saito、Naoki Miyata、Shosuke Kawanishi、Haruhiro Okuda

  DOI：10.1016/j.bmc.2007.03.029

  日期：2007.6

  Anthraquinones are typical photosensitizers used in photodynamic therapy (PDT). However, systemic toxicity is a major problem for anthraquinones due to their ability not only to bind DNA but also to cause oxidative stress even without photoirradiation. To avoid such disadvantages in cancer therapy, we designed and synthesized a novel 9-nitroanthracene derivative (1) as a precursor of anthraquinone. Under photoirradiation, I is converted into anthraquinone via generation of nitric oxide as confirmed by ESR. Strong DNA cleavage specifically at guanine under photoirradiation was also observed, characteristic of DNA-cleaving reactions by photoirradiated anthraquinones. We propose development of I as an alternative approach toward PDT that reduces the systemic toxicity of anthraquinone. (C) 2007 Elsevier Ltd. All rights reserved.