2-phenylthiazonaphthalic anhydride | 674784-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-phenylthiazonaphthalic anhydride
• 英文别名: 12-Phenyl-3-oxa-11-thia-13-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
• CAS: 674784-42-0
• 化学式: C₁₉H₉NO₃S
• 分子量: 331.351
• InChiKey: KNRJELIQFYKVHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-乙基-2-氨甲基吡咯烷 、 2-phenylthiazonaphthalic anhydride 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到5-((1-ethylpyrrolidin-2-yl)methyl)-9-phenyl-4H-benzo[de]thiazolo[5,4-g]isoquinoline-4,6(5H)-dione
  参考文献：
  名称：

  Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

  摘要：

  Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more ef.ciently than their R-enantiomers. S-enantiomer B-3 could photodamage DNA at 0.2 mu M and cleave supercoiled plasmid DNA from form I to form II completely at 50 mu M. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.104
• 作为产物：
  描述：

  4-溴-3-硝基-1,8-萘酐 在 溶剂黄146 、 sodium disulfide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 2-phenylthiazonaphthalic anhydride
  参考文献：
  名称：

  Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: synthesis, antitumor evaluation, and DNA photocleavage

  摘要：

  A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2, 1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B-3 (m-NO2) was found to be the strongest inhibitor for P388 with IC50 of 1.49 mu M, while B-2 was the most cytotoxic compound against A549 with IC50 of 12 mu M. B-4 (p-CH3) the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 mu M and total cleavage from form I to 100% form II at 50 mu M. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.045

文献信息

• Naphthalimide–thiazoles as novel photonucleases: molecular design, synthesis, and evaluation
  作者：Yonggang Li、Yufang Xu、Xuhong Qian、Baoyuan Qu

  DOI：10.1016/j.tetlet.2003.11.145

  日期：2004.2

  A new family of photonucleases, naphthalimide-thiazoles was synthesized and evaluated. These compounds intercalated into DNA efficiently and damaged DNA photochemically at concentrations as low as 5 muM. Mechanistic experiment suggests that a novel naphthalimide-thiazole radical produced via an excited triple state might be involved in the DNA photodamage. Different activity may arise from the impact of substituents at 2-phenyl ring of thiazole on the electron population of excited triple state according to AM1 semi-empirical calculation. (C) 2003 Elsevier Ltd. All rights reserved.