5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-6-carboxaldehyde | 1581721-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-6-carboxaldehyde
• CAS: 1581721-31-4
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: XZWHLCYZYVBTKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-6-carboxaldehyde 在 三溴化硼 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,4-di-isobutyl-8,9,10,11-tetrahydro-8,11-ethanobenzo[g]pyrimido[4,5-c]isoquinoline-1,3,7,12(2H,4H)-tetraone
  参考文献：
  名称：

  2,4-Dialkyl-8,9,10,11-tetrahydrobenzo[g]pyrimido[4,5-c]isoquinoline-1,3,7,12(2H,4H)-tetraones as new leads against Mycobacterium tuberculosis

  摘要：

  Given the re-emergence of tuberculosis in Europe and beyond, the search for novel bio-active compound classes against this disease is of utmost importance. As a result of a high intrinsic tolerance of the etiological agent, Mycobacterium tuberculosis, towards most antibiotics and xenobiotics, the search for such new compounds is far from trivial. Further exacerbated by the rapid generation and spread of drug resistant M. tuberculosis and fuelled by the HIV/AIDS pandemic, halting the tuberculosis epidemic is of paramount importance. As part of our program to design new 2-aza-anthraquinones with anti-mycobacterial activity, various dialkyltetrahydrobenzo[g]pyrimido[4,5-c]lisoquinolinetetraones were designed and synthesised. The compounds were submitted to a biological evaluation in which the activity against M.tb H37Rv(lux) was observed, as well as the acute toxicity towards J774 A.1 macrophages. From these results, the selectivity index was calculated. Furthermore, the activity of the most promising compounds was further studied against a multi-drug resistant LAM-1 strain and against intracellular replicating M.tb. The study was further extended with a comet assay and a VITOTOX (TM) assay to investigate the possibility of observable genotoxic effects caused by these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.024
• 作为产物：
  描述：

  在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 3.0h， 以97%的产率得到5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-6-carboxaldehyde
  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