5-(3-butylquinolin-2-yl)-3-(4-fluorophenyl)isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(3-butylquinolin-2-yl)-3-(4-fluorophenyl)isoxazole
• 化学式: C₂₂H₁₉FN₂O
• 分子量: 346.404
• InChiKey: LJFNWKFTZVNKML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.92
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  [3-(4-氟苯基)异噁唑-5-基]甲醇 在 Jones reagent 、 碘 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 6.58h， 生成 5-(3-butylquinolin-2-yl)-3-(4-fluorophenyl)isoxazole
  参考文献：
  名称：

  Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity

  摘要：

  The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having a-hydrogen using molecular iodine as catalyst and which yielded 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives 4. All the final compounds 4 were screened against four human cancer cell lines (A549, COLO 205, MDA-MB 231 and PC-3) and among these compounds 4n showed potent cytotoxicity against all the cell lines at IC50 values of < 12 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.038

文献信息

• Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity
  作者：P. Sambasiva Rao、C. Kurumurthy、B. Veeraswamy、Y. Poornachandra、C. Ganesh Kumar、B. Narsaiah

  DOI：10.1016/j.bmcl.2014.01.038

  日期：2014.3

  The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having a-hydrogen using molecular iodine as catalyst and which yielded 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives 4. All the final compounds 4 were screened against four human cancer cell lines (A549, COLO 205, MDA-MB 231 and PC-3) and among these compounds 4n showed potent cytotoxicity against all the cell lines at IC50 values of < 12 mu M. (C) 2014 Elsevier Ltd. All rights reserved.