1-(4'-amino-3'-nitrobiphenyl-3-yl)ethanone | 1352638-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4'-amino-3'-nitrobiphenyl-3-yl)ethanone
• CAS: 1352638-19-7
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: SALBFVXZURJQEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  86.23
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4'-amino-3'-nitrobiphenyl-3-yl)ethanone 在 三溴化硼 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.42h， 生成 N-(3'-acetyl-3-nitrobiphenyl-4-yl)-3,4-dihydroxy-5-methoxybenzamide
  参考文献：
  名称：

  Potent Galloyl-Based Selective Modulators Targeting Multidrug Resistance Associated Protein 1 and P-glycoprotein

  摘要：

  The multifactorial nature of chemotherapy failure in controlling cancer is often associated with the occurrence of multidrug resistance (MDR), a phenomenon likely related to the increased expression of members of the ATP binding cassette (ABC) transporter superfamily. In this respect, the most extensively characterized MDR transporters include ABCB1 (also known as MDR1 or P-glycoprotein) and ABCC1 (also known as MRP1) whose inhibition remains a priority to circumvent drug resistance. Herein, we report how the simple galloyl benzamide scaffold can be easily and properly decorated for the preparation of either MRP1 or P-gp highly selective inhibitors. In particular, some gallamides and pyrogallol-l-monomethyl ethers showed remarkable affinity and selectivity toward MRP1. On the other hand, trimethyl ether galloyl anilides, with few exceptions, exhibited moderate to very high and selective P-gp inhibition.

  DOI：

  10.1021/jm201305y
• 作为产物：
  描述：

  4-溴-2-硝基苯胺 、 3-乙酰基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以70%的产率得到1-(4'-amino-3'-nitrobiphenyl-3-yl)ethanone
  参考文献：
  名称：

  Potent Galloyl-Based Selective Modulators Targeting Multidrug Resistance Associated Protein 1 and P-glycoprotein

  摘要：

  The multifactorial nature of chemotherapy failure in controlling cancer is often associated with the occurrence of multidrug resistance (MDR), a phenomenon likely related to the increased expression of members of the ATP binding cassette (ABC) transporter superfamily. In this respect, the most extensively characterized MDR transporters include ABCB1 (also known as MDR1 or P-glycoprotein) and ABCC1 (also known as MRP1) whose inhibition remains a priority to circumvent drug resistance. Herein, we report how the simple galloyl benzamide scaffold can be easily and properly decorated for the preparation of either MRP1 or P-gp highly selective inhibitors. In particular, some gallamides and pyrogallol-l-monomethyl ethers showed remarkable affinity and selectivity toward MRP1. On the other hand, trimethyl ether galloyl anilides, with few exceptions, exhibited moderate to very high and selective P-gp inhibition.

  DOI：

  10.1021/jm201305y