ethyl 8-fluoro-5-(3-(4-methoxyphenoxy)propyl)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate | 1566528-25-3

• 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: ethyl 8-fluoro-5-(3-(4-methoxyphenoxy)propyl)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate
• CAS: 1566528-25-3
• 化学式: C₂₄H₂₇FN₂O₄
• 分子量: 426.488
• InChiKey: IQEIKOKMVYOESA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.93
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 8-fluoro-5-(3-(4-methoxyphenoxy)propyl)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以0.16 g的产率得到8-fluoro-5-(3-(4-methoxyphenoxy)propyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Novel Carboline Derivatives as Potent Antifungal Lead Compounds: Design, Synthesis, and Biological Evaluation

  摘要：

  A series of novel antifungal carboline derivatives was designed and synthesized, which showed broad-spectrum antifungal activity. Particularly, compound C38 showed comparable in vitro antifungal activity to fluconazole without toxicity to human embryonic lung cells. It also exhibited good fungicidal activity against both fluconazole-sensitive and -resistant Candida albicans cells and had potent inhibition activity against Candida albicans biofilm formation and hyphal growth. Moreover, C38 showed good synergistic antifungal activity in combination with fluconazole (FLC) against FLC-resistant Candida species. Preliminary mechanism studies revealed that C38 might act by inhibiting the synthesis of fungal cell wall.

  DOI：

  10.1021/ml400492t
• 作为产物：
  描述：

  4-甲氧基苯酚 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 4.25h， 生成 ethyl 8-fluoro-5-(3-(4-methoxyphenoxy)propyl)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate
  参考文献：
  名称：

  Novel Carboline Derivatives as Potent Antifungal Lead Compounds: Design, Synthesis, and Biological Evaluation

  摘要：

  A series of novel antifungal carboline derivatives was designed and synthesized, which showed broad-spectrum antifungal activity. Particularly, compound C38 showed comparable in vitro antifungal activity to fluconazole without toxicity to human embryonic lung cells. It also exhibited good fungicidal activity against both fluconazole-sensitive and -resistant Candida albicans cells and had potent inhibition activity against Candida albicans biofilm formation and hyphal growth. Moreover, C38 showed good synergistic antifungal activity in combination with fluconazole (FLC) against FLC-resistant Candida species. Preliminary mechanism studies revealed that C38 might act by inhibiting the synthesis of fungal cell wall.

  DOI：

  10.1021/ml400492t