3,5-dimethyl-benzoic acid 1-oxo-3-thioxo-1H,3H-benzo[de]isoquinolin-2-yl ester

• 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: 3,5-dimethyl-benzoic acid 1-oxo-3-thioxo-1H,3H-benzo[de]isoquinolin-2-yl ester
• 英文别名: (1-Oxo-3-sulfanylidenebenzo[de]isoquinolin-2-yl) 3,5-dimethylbenzoate
• 化学式: C₂₁H₁₅NO₃S
• 分子量: 361.421
• InChiKey: UJESVODQMPJPSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  78.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二甲基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 反应 3.75h， 生成 3,5-dimethyl-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

文献信息

• SULFUR-CONTAINING NAPHTHALIMIDE DERIVATIVES
  申请人：Qian Xuhong

  公开号：US20080234287A1

  公开（公告）日：2008-09-25

  The invention discloses novel sulfur-containing naphthalimide derivatives, and the preparation and uses thereof. The conjugated plane of naphthalimide derivatives of the invention is enlarged by incorporating 5- or 6-membered heteroaromatic ring and/or introducing S heteroatom, thus increasing the anti-tumor activity of naphthalimide. The compounds of the invention displays significant inhibiting activities to the proliferation of various tumor cells such as human lung cancer, gastric cancer, liver cancer, leucocythemia and the like. The inhibition of cell proliferation is dose-dependent.
• US7541463B2
  申请人：——

  公开号：US7541463B2

  公开（公告）日：2009-06-02
• N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: synthesis, evaluation, and substituents’ effect
  作者：Yufang Xu、Xiayu Huang、Xuhong Qian、Wei Yao

  DOI：10.1016/j.bmc.2004.02.013

  日期：2004.5

  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.