2-(9-Oxoacridin-10-yl)ethyl 2-[4-(2-methylpropyl)phenyl]propanoate | 1416368-30-3

• 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: 2-(9-Oxoacridin-10-yl)ethyl 2-[4-(2-methylpropyl)phenyl]propanoate
• 英文别名: 2-(9-oxoacridin-10-yl)ethyl 2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 1416368-30-3
• 化学式: C₂₈H₂₉NO₃
• 分子量: 427.543
• InChiKey: WJIXCIQBVXTYFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吖啶酮 在 4-二甲氨基吡啶 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.08h， 生成 2-(9-Oxoacridin-10-yl)ethyl 2-[4-(2-methylpropyl)phenyl]propanoate
  参考文献：
  名称：

  Hybrid fluorescent conjugates of COX-2 inhibitors: Search for a COX-2 isozyme imaging cancer biomarker

  摘要：

  The observation that the cyclooxygenase-2 (COX-2) isozyme is over-expressed in multiple types of cancer, relative to that in adjacent non-cancerous tissue, prompted this investigation to prepare a group of hybrid fluorescent conjugates wherein the COX inhibitors ibuprofen, (S)-naproxen, acetyl salicylic acid, a chlororofecoxib analog and celecoxib were coupled via a linker group to an acridone, dansyl or rhodamine B fluorophore. Within this group of compounds, the ibuprofen-acridone conjugate (10) showed potent and selective COX-2 inhibition (COX-2 IC50 = 0.67 mu M; SI = 110.6), but its fluorescence emission (lambda(em) = 417, 440 nm) was not suitable for fluorescent imaging of cancer cells that over-express the COX-2 isozyme. In comparison, the celecoxib-dansyl conjugate (25) showed a slightly lower COX-2 potency and selectivity (COX-2 IC50 = 1.1 mu M; SI > 90) than the conjugate 10, and it possesses a better fluorescence emission (lambda(em) = 500 nm). Ultimately, a celecoxib-rhodamine B conjugate (28) that exhibited moderate COX-2 potency and selectivity (COX-2 IC50 = 3.9 mu M; SI > 25) having the best fluorescence emission (lambda(em) = 580 nm) emerged as the most promising biomarker for fluorescence imaging using a colon cancer cell line that over-expresses the COX-2 isozyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.131

文献信息

• Hybrid fluorescent conjugates of COX-2 inhibitors: Search for a COX-2 isozyme imaging cancer biomarker
  作者：Atul Bhardwaj、Jatinder Kaur、Sai Kiran Sharma、Zhangjian Huang、Frank Wuest、Edward E. Knaus

  DOI：10.1016/j.bmcl.2012.10.131

  日期：2013.1

  The observation that the cyclooxygenase-2 (COX-2) isozyme is over-expressed in multiple types of cancer, relative to that in adjacent non-cancerous tissue, prompted this investigation to prepare a group of hybrid fluorescent conjugates wherein the COX inhibitors ibuprofen, (S)-naproxen, acetyl salicylic acid, a chlororofecoxib analog and celecoxib were coupled via a linker group to an acridone, dansyl or rhodamine B fluorophore. Within this group of compounds, the ibuprofen-acridone conjugate (10) showed potent and selective COX-2 inhibition (COX-2 IC50 = 0.67 mu M; SI = 110.6), but its fluorescence emission (lambda(em) = 417, 440 nm) was not suitable for fluorescent imaging of cancer cells that over-express the COX-2 isozyme. In comparison, the celecoxib-dansyl conjugate (25) showed a slightly lower COX-2 potency and selectivity (COX-2 IC50 = 1.1 mu M; SI > 90) than the conjugate 10, and it possesses a better fluorescence emission (lambda(em) = 500 nm). Ultimately, a celecoxib-rhodamine B conjugate (28) that exhibited moderate COX-2 potency and selectivity (COX-2 IC50 = 3.9 mu M; SI > 25) having the best fluorescence emission (lambda(em) = 580 nm) emerged as the most promising biomarker for fluorescence imaging using a colon cancer cell line that over-expresses the COX-2 isozyme. (C) 2012 Elsevier Ltd. All rights reserved.