4-(2-bromoethanoyl)-N-(2-nitrophenyl)-benzamide | 1330128-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-bromoethanoyl)-N-(2-nitrophenyl)-benzamide
• 英文别名: 4-(2-bromoacetyl)-N-(2-nitrophenyl)benzamide
• CAS: 1330128-24-9
• 化学式: C₁₅H₁₁BrN₂O₄
• 分子量: 363.167
• InChiKey: UJZHUGYBQSKRCU-UHFFFAOYSA-N

物化性质

• 沸点：
  441.9±35.0 °C(predicted)
• 密度：
  1.615±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-bromoethanoyl)-N-(2-nitrophenyl)-benzamide 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and docking studies on benzamide derivatives as histone deacetylase inhibitors

  摘要：

  A series of benzamide derivatives including two scaffolds were designed and synthesized as potential histone deacetylase inhibitors. Most of synthesized compounds showed moderate enzymatic potency at the same order of magnitude, and compound 12b possessed better potency to the positive control (3.8 mu M vs 13.0 mu M). It also showed a 50-fold increase in vitro anticancer activity against DU-145 cell-lines. Molecular docking studies were carried out and used to explain the structure-activity relationships observed in vitro. Then we found that the cavity surrounded by ASP104, HIS33, PRO34 and PHE155 may be crucial for the inhibitors' activity. The docking results provide some useful information for future design of more potent inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.001
• 作为产物：
  描述：

  4-acetyl-N-(2-nitrophenyl)benzamide 在 溴 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到4-(2-bromoethanoyl)-N-(2-nitrophenyl)-benzamide
  参考文献：
  名称：

  Design, synthesis and docking studies on benzamide derivatives as histone deacetylase inhibitors

  摘要：

  A series of benzamide derivatives including two scaffolds were designed and synthesized as potential histone deacetylase inhibitors. Most of synthesized compounds showed moderate enzymatic potency at the same order of magnitude, and compound 12b possessed better potency to the positive control (3.8 mu M vs 13.0 mu M). It also showed a 50-fold increase in vitro anticancer activity against DU-145 cell-lines. Molecular docking studies were carried out and used to explain the structure-activity relationships observed in vitro. Then we found that the cavity surrounded by ASP104, HIS33, PRO34 and PHE155 may be crucial for the inhibitors' activity. The docking results provide some useful information for future design of more potent inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.001