(R)-2-bromo-N-(1-hydroxybutan-2-yl)benzamide | 1359049-06-1

• 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: (R)-2-bromo-N-(1-hydroxybutan-2-yl)benzamide
• 英文别名: 2-bromo-N-[(2R)-1-hydroxybutan-2-yl]benzamide
• CAS: 1359049-06-1
• 化学式: C₁₁H₁₄BrNO₂
• 分子量: 272.142
• InChiKey: GEKMBHNFONLMET-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基丁醇 、 2-溴苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以57%的产率得到(R)-2-bromo-N-(1-hydroxybutan-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol – The crucial role of the configuration

  摘要：

  The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 mu M-14.03 mu M. Five of the most active compounds 11, 22, 23, 31 and 42(5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H(37)Rv showing no activity even at 20-32 fold higher concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.035

文献信息

• Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol – The crucial role of the configuration
  作者：Georgi M. Dobrikov、Violeta Valcheva、Margarita Stoilova-Disheva、Georgi Momekov、Pavleta Tzvetkova、Angel Chimov、Vladimir Dimitrov

  DOI：10.1016/j.ejmech.2011.11.035

  日期：2012.2

  The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 mu M-14.03 mu M. Five of the most active compounds 11, 22, 23, 31 and 42(5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H(37)Rv showing no activity even at 20-32 fold higher concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.