2-methoxy-6-(5-methoxy-1H-indol-3-yl)-5H-benzo[b]carbazole | 1027786-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-methoxy-6-(5-methoxy-1H-indol-3-yl)-5H-benzo[b]carbazole
• 英文别名: 2-methoxy-6-(5-methoxy-1H-indol-3-yl)-5H-benzo[b]carbazole
• CAS: 1027786-91-9
• 化学式: C₂₆H₂₀N₂O₂
• 分子量: 392.457
• InChiKey: LQQFTLOXWDBMSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.04
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 邻苯二甲醛 在 iron(II) chloride 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以85%的产率得到2-methoxy-6-(5-methoxy-1H-indol-3-yl)-5H-benzo[b]carbazole
  参考文献：
  名称：

  铁-催化的环加成吲哚和ö -phthalaldehyde为苯并的合成[ b ]与TMSCl-或酸响应型特性咔唑†

  摘要：

  一锅铁催化的吲哚和邻苯二甲醛环加成反应通过顺序形成碳-碳键的加成，涉及分子内烷基化的环化和芳构化形成苯环，得到吲哚基苯并[ b ]咔唑。另外，研究了这种吲哚基苯并[ b ]咔唑的荧光性质，其中在添加三甲基氯硅烷（TMSCl）或三氟乙酸（TFA）时观察到荧光强度的显着变化。

  DOI：

  10.1039/c4ra08012b

文献信息

• WO2008/58402
  申请人：——

  公开号：——

  公开（公告）日：——
• Antistaphylococcal evaluation of indole–naphthalene hybrid analogs
  作者：Kerolos Ashraf、Kaveh Yasrebi、Emmanuel Tola Adeniyi、Tobias Hertlein、Knut Ohlsen、Michael Lalk、Frank Erdmann、Andreas Hilgeroth

  DOI：10.2147/dddt.s184965

  日期：——

  Resistance developments against established antibiotics are an emerging problem for antibacterial therapies. Infections with Staphylococcus aureus and methicillin-resistant S. aureus (MRSA) have become more difficult to treat with standard antibiotics that often fail, especially against MRSA. In consequence, novel antibiotics are urgently needed. Antibiotics from natural sources own complicated structures that cause difficulties for a chemical synthetic production. We developed novel small-molecule antibacterials that are easily accessible in a simple one-pot synthesis. The central indolonaphthalene core is substituted with indole residues at various positions. Both the varied indole substitutions and their positions at the molecular scaffold influence the determined antibacterial activity against the evaluated Staphylococcus strains. Best activities have been found for 5-chloro, -cyano, and -hydroxyl indole substitutions. Therefore, first promising lead compounds could be identified that are nontoxic in human HEK and SH-SY5Y cells and exceed the activity of used standard antibiotics, especially against MRSA.