N-hydroxy-thionaphthalimide | 371114-58-8

• 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: N-hydroxy-thionaphthalimide
• 英文别名: 2-Hydroxy-3-sulfanylidenebenzo[de]isoquinolin-1-one
• CAS: 371114-58-8
• 化学式: C₁₂H₇NO₂S
• 分子量: 229.259
• InChiKey: KDKGUUSASIYPNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-二氯苯甲酰氯 、 N-hydroxy-thionaphthalimide 在 三乙胺 作用下， 反应 0.75h， 生成 3,5-dichloro-benzoic acid 1-oxo-3-thioxo-1H,3H-benzo[de]isoquinolin-2-yl ester
  参考文献：
  名称：

  N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: synthesis, evaluation, and substituents’ effect

  摘要：

  Novel N-Aroyloxylthioxo-naphthalimides as highly efficient 'time-resolved' DNA photocleavers of aroyloxyl radicals type were designed and synthesized. The substituents at the aroyloxyl moiety have an important and unusual influence on the DNA photocleavage, and DNA photodamages of the compounds were unusually not depended on the electronic effects of substituents on the corresponding oxygen-centered radicals. With AM1 semi-empirical quantum calculation, it was found that their photocleaving activities were correlated with the densities of electron clouds on the N-O bonds in the triplet state. N-(m-Diehloro-benzoyloxy)thioxo-naphthalimide could photodamage DNA effectively at less than the concentration of 2 mum. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.013
• 作为产物：
  描述：

  N-羟基-1,8-萘二甲酰亚胺 在 劳森试剂 作用下， 以 氯苯 为溶剂， 反应 1.0h， 生成 N-hydroxy-thionaphthalimide
  参考文献：
  名称：

  N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: synthesis, evaluation, and substituents’ effect

  摘要：

  Novel N-Aroyloxylthioxo-naphthalimides as highly efficient 'time-resolved' DNA photocleavers of aroyloxyl radicals type were designed and synthesized. The substituents at the aroyloxyl moiety have an important and unusual influence on the DNA photocleavage, and DNA photodamages of the compounds were unusually not depended on the electronic effects of substituents on the corresponding oxygen-centered radicals. With AM1 semi-empirical quantum calculation, it was found that their photocleaving activities were correlated with the densities of electron clouds on the N-O bonds in the triplet state. N-(m-Diehloro-benzoyloxy)thioxo-naphthalimide could photodamage DNA effectively at less than the concentration of 2 mum. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.013

文献信息

• N-Aroyloxynaphthalimides as novel highly efficient DNA photocleavers: substituent effects
  作者：Xuhong Qian、Wei Yao、Gang Chen、Xiayu Huang、Ping Mao

  DOI：10.1016/s0040-4039(01)01214-x

  日期：2001.8

  A novel DNA photocleaver family of N-benzovloxythioxonaphthalimides. which show improved DNA intercalation and photocleaving activity compared with their oxo- counterparts, were synthesized and evaluated. The substituents on the benzene ring of the benzoyloxy moiety have an important and unusual influence on the DNA photocleaving activity. N-(p-Methoxylbenzovloxy)thioxonaphthalimide is able to photocleave DNA at low concentration (5 muM) with 'time-resolved' and pH independent properties. (C) 2001 Elsevier Science Ltd. All rights reserved.