5-(3-fluorophenyl)-3-(5-methoxy-1H-indol-2-yl)-1,2-oxazole | 1413923-22-4

• 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: 5-(3-fluorophenyl)-3-(5-methoxy-1H-indol-2-yl)-1,2-oxazole
• CAS: 1413923-22-4
• 化学式: C₁₈H₁₃FN₂O₂
• 分子量: 308.312
• InChiKey: QQOGIMAOWJMOMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (9ci)-5-甲氧基-1H-吲哚-2-羰酰氯 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 盐酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 5-(3-fluorophenyl)-3-(5-methoxy-1H-indol-2-yl)-1,2-oxazole 、 5-(1-methylindol-2-yl)-3-(3-methoxyphenyl)isoxazole
  参考文献：
  名称：

  Synthesis and evaluation of indole-containing 3,5-diarylisoxazoles as potential pro-apoptotic antitumour agents

  摘要：

  A series of novel indole-containing diarylisoxazoles has been synthesised, based on our previous work on the synthesis and pro-apoptotic antitumour activity of indole-based diaryl 1,2,4-oxadiazoles. Concise synthetic routes to both 3-(indol-2-yl)-5-phenylisoxazoles and 5-(indol-2-yl)-3-phenylisoxazoles have been developed with full regiochemical control, bearing substituents on the indole ring, indole nitrogen, and/or phenyl group. Additionally a series of the related 5-(1H-indol-5-yl)-3-phenylisoxazoles has been prepared. In vitro evaluation in human cancer cell lines Colo320 (colon) and Calu-3 (lung) revealed preferential antiproliferative activity within the 5-(indol-5-yl)-3-phenylisoxazole series (low micromolar IC50). Further analysis revealed the ability of the indol-5-yl series to induce expression of effector caspases-3 and -7, and retention of viability of the human bronchial smooth muscle cell (BSMC) control cell population (particularly for compounds 18c and 18e). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.009