3-(5-chlorofuran-2-yl)-5-(fluoromethyl)-4-phenylisoxazole | 1613135-55-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-(5-chlorofuran-2-yl)-5-(fluoromethyl)-4-phenylisoxazole
• 英文别名: 3-(5-chlorofuran-2-yl)-5-((18F)fluoranylmethyl)-4-phenyl-1,2-oxazole
• CAS: 1613135-55-9
• 化学式: C₁₄H₉ClFNO₂
• 分子量: 276.684
• InChiKey: CXWURKYTSBPLCE-GKTGUEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [3-(5-chlorofuran-2-yl)-4-phenylisoxazol-5-yl]methyl 4-methylbenzenesulfonate 在 C₂₂H₃₆N₂O₆*K⁽¹⁺⁾*⁽¹⁸⁾F^(1-) 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以18%的产率得到3-(5-chlorofuran-2-yl)-5-(fluoromethyl)-4-phenylisoxazole
  参考文献：
  名称：

  PET radiotracer [18F]-P6 selectively targeting COX-1 as a novel biomarker in ovarian cancer: Preliminary investigation

  摘要：

  Cyclooxygenase-1 (COX-1), but not COX-2, is expressed at high levels in the early stages of human epithelial ovarian cancer where it seems to play a key role in cancer onset and progression. As a consequence, COX-1 is an ideal biomarker for early ovarian cancer detection. A series of novel fluorinated COX-1-targeted imaging agents derived from P6 was developed by using a highly selective COX-1 inhibitor as a lead compound. Among these new compounds, designed by structural modification of P6, 3-(5-chlorofuran-2-yl)-5-(fluoromethyl)-4-phenylisoxazole ([(18/19)F]-P6) is the most promising derivative [IC50 = 2.0 μM (purified oCOX-1) and 1.37 μM (hOVCAR-3 cell COX-1)]. Its tosylate precursor was also prepared and, a method for radio[(18)F]chemistry was developed and optimized. The radiochemistry was carried out using a carrier-free K(18)F/Kryptofix 2.2.2 complex, that afforded [(18)F]-P6 in good radiochemical yield (18%) and high purity (>95%). In vivo PET/CT imaging data showed that the radiotracer [(18)F]-P6 was selectively taken up by COX-1-expressing ovarian carcinoma (OVCAR 3) tumor xenografts as compared with the normal leg muscle. Our results suggest that [(18)F]-P6 might be an useful radiotracer in preclinical and clinical settings for in vivo PET-CT imaging of tissues that express elevated levels of COX-1.

  DOI：

  10.1016/j.ejmech.2014.04.074