5,8-dihydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carboxaldehyde | 1600523-76-9

• 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-dihydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carboxaldehyde
• 英文别名: 5,8-dihydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carbaldehyde；3,6-Dihydroxytricyclo[6.2.1.02,7]undeca-2,4,6-triene-4-carbaldehyde
• CAS: 1600523-76-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: OFZGJWGMUKHEHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,8-dihydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carboxaldehyde 在 caesium carbonate 、 magnesium bromide ethyl etherate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 32.5h， 生成 8-(benzyloxy)-6-formyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl trifluoromethanesulfonate
  参考文献：
  名称：

  [EN] ARYLALKYLAMINE COMPOUNDS AS CALCIUM SENSING RECEPTOR MODULATORS
  [FR] COMPOSÉS D'ARYLALKYLAMINE COMME MODULATEURS DES RÉCEPTEURS SENSIBLES AU CALCIUM

  摘要：

  该发明涉及式（I）的芳基烷胺化合物及其药用可接受的盐，其中取代基如本文所述，并其在医学上用于治疗与钙感受受体（CaSR）调节剂相关的疾病、疾病。该发明还涉及含有这类化合物的药物组合物，用于治疗与钙感受受体（CaSR）调节剂相关的疾病、疾病。

  公开号：

  WO2017037616A1
• 作为产物：
  描述：

  5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carboxaldehyde 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以81%的产率得到5,8-dihydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carboxaldehyde
  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