4-hydroxyl-3-nitro-1,8-naphthalic anhydride | 134870-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxyl-3-nitro-1,8-naphthalic anhydride
• 英文别名: 8-hydroxy-7-nitro-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
• CAS: 134870-45-4
• 化学式: C₁₂H₅NO₆
• 分子量: 259.175
• InChiKey: CFIBSUGMQQSVHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxyl-3-nitro-1,8-naphthalic anhydride 在 palladium on activated charcoal 氢气 作用下， 反应 3.5h， 生成 12-Methyl-3,11-dioxa-13-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
  参考文献：
  名称：

  Novel and highly efficient DNA photocleavers: hydroperoxides of heterocyclic-fused naphthalimides

  摘要：

  A series of novel hydroperoxides of heterocyclic-fused naphthalimides were designed, synthesized and exhibited excellent DNA photonicking activities. Among these compounds, the benzothiophenonaphthalimide-type reagent proved to be the most efficient, it can induce single-strand nicks in duplex DNA at micromolar concentration upon illumination. The relationship between the molecular structure and cleaving activities was discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01304-6
• 作为产物：
  描述：

  4-溴-3-硝基-1,8-萘酐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 8.0h， 以85%的产率得到4-hydroxyl-3-nitro-1,8-naphthalic anhydride
  参考文献：
  名称：

  氧杂环稠合萘二甲酰亚胺作为抗肿瘤剂的合成与生物学评价

  摘要：

  制备了三个系列的新颖的氧-杂环稠合的萘二甲酰亚胺衍生物（8a - 8f，13a - 13d，17a - 17d）。新合成的化合物及其硫杂环稠合的类似物（1a - 1c，2a - 2d，3a - 3c）显示出有效的抗增殖活性，与其结构密切相关。进一步的研究表明，所有代表性化合物13a，2a和17a，3a与阿莫那肽相似，它对topo II具有很强的抑制活性，并且对topo I的抑制作用也很强，以前很少报道过萘二甲酰亚胺衍生物。初步探索证明了他们的DNA序列偏好。总而言之，双重的topo I / topo II抑制作用和DNA序列优先选择可能有助于增强肿瘤的选择性并克服耐药性。

  DOI：

  10.1016/j.ejmech.2012.12.039

文献信息

• PETERS, A. T.;DEKHORDI, M. MEHDI SHAHAB, J. SOC. DYERS AND COLOUR., 106,(1990) N, C. 275-280
  作者：PETERS, A. T.、DEKHORDI, M. MEHDI SHAHAB

  DOI：——

  日期：——
• Oxo-heterocyclic fused naphthalimides as antitumor agents: Synthesis and biological evaluation
  作者：Shaoying Tan、Hong Yin、Zhuo Chen、Xuhong Qian、Yufang Xu

  DOI：10.1016/j.ejmech.2012.12.039

  日期：2013.4

  Three series of novel oxo-heterocyclic fused naphthalimide derivatives (8a–8f, 13a–13d, 17a–17d) were prepared. The newly-synthesized compounds, and their thio-heterocyclic fused analogs (1a–1c, 2a–2d, 3a–3c) exhibited potent antiproliferative activity correlated well with their structure. Further research demonstrated that all the representative compounds 13a, 2a and 17a, 3a showed strong inhibition

  制备了三个系列的新颖的氧-杂环稠合的萘二甲酰亚胺衍生物（8a - 8f，13a - 13d，17a - 17d）。新合成的化合物及其硫杂环稠合的类似物（1a - 1c，2a - 2d，3a - 3c）显示出有效的抗增殖活性，与其结构密切相关。进一步的研究表明，所有代表性化合物13a，2a和17a，3a与阿莫那肽相似，它对topo II具有很强的抑制活性，并且对topo I的抑制作用也很强，以前很少报道过萘二甲酰亚胺衍生物。初步探索证明了他们的DNA序列偏好。总而言之，双重的topo I / topo II抑制作用和DNA序列优先选择可能有助于增强肿瘤的选择性并克服耐药性。
• Novel and highly efficient DNA photocleavers: hydroperoxides of heterocyclic-fused naphthalimides
  作者：Wei Yao、Xuhong Qian、Qingyan Hu

  DOI：10.1016/s0040-4039(00)01304-6

  日期：2000.9

  A series of novel hydroperoxides of heterocyclic-fused naphthalimides were designed, synthesized and exhibited excellent DNA photonicking activities. Among these compounds, the benzothiophenonaphthalimide-type reagent proved to be the most efficient, it can induce single-strand nicks in duplex DNA at micromolar concentration upon illumination. The relationship between the molecular structure and cleaving activities was discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.