6-(1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-5,8-dione | 1581721-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 6-(1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-5,8-dione
• CAS: 1581721-40-5
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: CGOBKVZJBIPZLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-5,8-dione 在 三氟化硼乙醚 、 ammonium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-tert-butyl-1,2,3,4,8,9,10,11-octahydro-8,11-ethanobenzo[j]phenanthridine-7,12-dione
  参考文献：
  名称：

  1,2,3,4,8,9,10,11-Octahydrobenzo[j]phenanthridine-7,12-diones as New Leads against Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) continues to be a worldwide health problem with over 1.4 million deaths each year. Despite efforts to develop more effective vaccines, more reliable diagnostics, and chemotherapeutics, tuberculosis remains a threat to global health, fueled by the HIV pandemic and the rapid generation of drug resistance. The exploration of novel drugs to serve as a companion drug for existing drugs is of paramount importance. As part of our program to design new 2-aza-anthraquinones with antimycobacterial activity, various tetrahydro- and octahydrobenzo[j]phenanthridinediones were synthesized. These compounds showed high in vitro potency against Mycobacterium tuberculosis, the etiological agent of TB and against other clinically relevant mycobacterial species at submicromolar concentrations. The susceptibility of a multidrug resistant strain toward these compounds and their ability to target intracellular replicating Mycobacterium tuberculosis was demonstrated. Next to the acute toxicity, the genotoxicity of these compounds was investigated. Often overlooked in studies, genotoxicity could be dismissed for the investigated compounds, making them a promising scaffold in TB drug research.

  DOI：

  10.1021/jm401735w
• 作为产物：
  描述：

  在 ammonium cerium (IV) nitrate 、 palladium on activated charcoal 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 7.05h， 生成 6-(1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-5,8-dione
  参考文献：
  名称：

  1,2,3,4,8,9,10,11-Octahydrobenzo[j]phenanthridine-7,12-diones as New Leads against Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) continues to be a worldwide health problem with over 1.4 million deaths each year. Despite efforts to develop more effective vaccines, more reliable diagnostics, and chemotherapeutics, tuberculosis remains a threat to global health, fueled by the HIV pandemic and the rapid generation of drug resistance. The exploration of novel drugs to serve as a companion drug for existing drugs is of paramount importance. As part of our program to design new 2-aza-anthraquinones with antimycobacterial activity, various tetrahydro- and octahydrobenzo[j]phenanthridinediones were synthesized. These compounds showed high in vitro potency against Mycobacterium tuberculosis, the etiological agent of TB and against other clinically relevant mycobacterial species at submicromolar concentrations. The susceptibility of a multidrug resistant strain toward these compounds and their ability to target intracellular replicating Mycobacterium tuberculosis was demonstrated. Next to the acute toxicity, the genotoxicity of these compounds was investigated. Often overlooked in studies, genotoxicity could be dismissed for the investigated compounds, making them a promising scaffold in TB drug research.

  DOI：

  10.1021/jm401735w