4-bromo-N-(2-hydroxy-2-phenylethyl)benzamide | 413583-46-7

• 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-bromo-N-(2-hydroxy-2-phenylethyl)benzamide
• CAS: 413583-46-7
• 化学式: C₁₅H₁₄BrNO₂
• mdl: MFCD00430364
• 分子量: 320.186
• InChiKey: YEDYXMUOPFFPBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-N-(2-hydroxy-2-phenylethyl)benzamide 、 甲基磺酸酐 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 C₁₆H₁₆BrNO₄S
  参考文献：
  名称：

  Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides

  摘要：

  A series of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides were prepared, using an efficient three-to five-step synthesis, and evaluated for their inhibitory activity against human cytochrome P450C24A1 (CYP24A1) hydroxylase. Inhibition ranged from IC50 0.3-72 mu M compared with the standard ketoconazole IC50 0.52 mu M, with the styryl derivative (11c) displaying enhanced activity (IC50 = 0.3 mu M) compared with the standard, providing a useful preliminary lead for drug development. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.011
• 作为产物：
  描述：

  N-(4-溴苯甲酰基)咪唑 、 2-氨基-1-苯乙醇 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-bromo-N-(2-hydroxy-2-phenylethyl)benzamide
  参考文献：
  名称：

  Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides

  摘要：

  A series of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides were prepared, using an efficient three-to five-step synthesis, and evaluated for their inhibitory activity against human cytochrome P450C24A1 (CYP24A1) hydroxylase. Inhibition ranged from IC50 0.3-72 mu M compared with the standard ketoconazole IC50 0.52 mu M, with the styryl derivative (11c) displaying enhanced activity (IC50 = 0.3 mu M) compared with the standard, providing a useful preliminary lead for drug development. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.011

文献信息

• Selective Amidation of Unprotected Amino Alcohols Using Surfactant-in-Water Technology: A Highly Desirable Alternative to Reprotoxic Polar Aprotic Solvents
  作者：Michael Parmentier、Mona K. Wagner、Kevin Magra、Fabrice Gallou

  DOI：10.1021/acs.oprd.6b00133

  日期：2016.6.17

  A general selective and environmentally friendly method for the formation of amide bonds using a surfactant in water as medium is described. The use of readily available 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDC) and hydroxybenzotriazol (HOBt) as a coupling system, N-methylmorpholine (NMM), and TPGS-750-M represents mild conditions allowing for chemoselective amidation of unprotected amino

  描述了使用表面活性剂在水中作为介质来形成酰胺键的一般选择性和环境友好的方法。使用现成的1-乙基-3-（3-（二甲基氨基）丙基）碳二亚胺（EDC）和羟基苯并三唑（HOBt）作为偶联体系，N-甲基吗啉（NMM）和TPGS-750-M代表温和的条件，允许用于未保护的氨基醇的化学选择性酰胺化。给出了与经典极性非质子溶剂（如二甲基甲酰胺或乙腈）的比较结果。