2-Bromo-N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-acetamide | 206993-31-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-Bromo-N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-acetamide
• 英文别名: 2-bromo-N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]acetamide
• CAS: 206993-31-9
• 化学式: C₁₀H₂₂BrNO₂Si
• 分子量: 296.28
• InChiKey: LGKQCERPLLVMHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-acetamide 、 (9S)-9-dihydro-N-desmethyl-N-isopropylerythromycin A 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 2.17h， 以0.02 g的产率得到
  参考文献：
  名称：

  Structure−Activity Relationships of 9-Substituted-9-Dihydroerythromycin-Based Motilin Agonists: Optimizing for Potency and Safety

  摘要：

  A series of 9-dihydro-9-acetamido-N-desmethyl-N-isopropyl erythromycin A analogues and related derivatives was generated as motilin agonists. The compounds were optimized for potency while showing both minimal antibacterial activity and hERG inhibition. As the substituent on the amide was increased in lipophilicity the potency and hERG inhibition increased, while polar groups lowered potency, without significantly impacting hERG inhibition. The N-methyl acetamide 7a showed the optimal in vitro profile and was probed further by varying the chain length to the macrocycle as well as changing the macrocycle scaffold. 7a remained the compound with the best in vitro properties.

  DOI：

  10.1021/jm901107f
• 作为产物：
  描述：

  溴乙酰溴 、 2-(叔丁基二甲基硅氧基)乙胺 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 2-Bromo-N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-acetamide
  参考文献：
  名称：

  Structure−Activity Relationships of 9-Substituted-9-Dihydroerythromycin-Based Motilin Agonists: Optimizing for Potency and Safety

  摘要：

  A series of 9-dihydro-9-acetamido-N-desmethyl-N-isopropyl erythromycin A analogues and related derivatives was generated as motilin agonists. The compounds were optimized for potency while showing both minimal antibacterial activity and hERG inhibition. As the substituent on the amide was increased in lipophilicity the potency and hERG inhibition increased, while polar groups lowered potency, without significantly impacting hERG inhibition. The N-methyl acetamide 7a showed the optimal in vitro profile and was probed further by varying the chain length to the macrocycle as well as changing the macrocycle scaffold. 7a remained the compound with the best in vitro properties.

  DOI：

  10.1021/jm901107f

文献信息

• Structure−Activity Relationships of 9-Substituted-9-Dihydroerythromycin-Based Motilin Agonists: Optimizing for Potency and Safety
  作者：Simon J. Shaw、Yue Chen、Hao Zheng、Hong Fu、Mark A. Burlingame、Saul Marquez、Yong Li、Mark Claypool、Christopher W. Carreras、William Crumb、Dwight J. Hardy、David C. Myles、Yaoquan Liu

  DOI：10.1021/jm901107f

  日期：2009.11.12

  A series of 9-dihydro-9-acetamido-N-desmethyl-N-isopropyl erythromycin A analogues and related derivatives was generated as motilin agonists. The compounds were optimized for potency while showing both minimal antibacterial activity and hERG inhibition. As the substituent on the amide was increased in lipophilicity the potency and hERG inhibition increased, while polar groups lowered potency, without significantly impacting hERG inhibition. The N-methyl acetamide 7a showed the optimal in vitro profile and was probed further by varying the chain length to the macrocycle as well as changing the macrocycle scaffold. 7a remained the compound with the best in vitro properties.