(E)-methyl 5-(3-(thiophen-2-yl)allylamino)-2-morpholinobenzoate | 1116688-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (E)-methyl 5-(3-(thiophen-2-yl)allylamino)-2-morpholinobenzoate
• 英文别名: methyl 2-morpholin-4-yl-5-[[(E)-3-thiophen-2-ylprop-2-enyl]amino]benzoate
• CAS: 1116688-83-5
• 化学式: C₁₉H₂₂N₂O₃S
• 分子量: 358.461
• InChiKey: PQALIRIJPTWSLE-DUXPYHPUSA-N

物化性质

• 熔点：
  131 °C(Solvent: Dichloromethane)
• 沸点：
  573.2±50.0 °C(predicted)
• 密度：
  1.257±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-methyl 5-(3-(thiophen-2-yl)allylamino)-2-morpholinobenzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以78%的产率得到(E)-5-(3-(thiophen-2-yl)allylamino)-2-morpholinobenzoic acid
  参考文献：
  名称：

  Synthesis and structure activity relationship studies of novel Staphylococcus aureus Sortase A inhibitors

  摘要：

  Synthetic methods have been developed for lead Sortase A inhibitors identified from previous studies. Several derivatives of the lead inhibitor were synthesized to derive preliminary structure activity relationships (SAR). Different regions of the lead inhibitor that are critical for the enzyme activity have been determined by systematic SAR studies. The E stereochemistry of the lead compound was found to be critical for its activity. Replacement of the E double bond with Z double bond or a rigid triple bond reduced the enzyme inhibitory activity in most cases. Reduction of the double bond to a C-C single bond resulted in complete loss of activity. Amide carbonyl and NH groups were also found to be crucial for the activity of this class of inhibitors, as well. The morpholine ring oxygen atom was also found to be an important factor for the activity of the lead inhibitor. Preliminary SAR studies led to the identification of compounds with improved enzyme inhibition. The most active compound was found to have an IC(50) value of 58 mu M against the enzyme. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.024
• 作为产物：
  描述：

  (2E)-3-(2-噻吩基)丙烯醛 、 methyl 5-amino-2-morpholinobenzoate 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以88%的产率得到(E)-methyl 5-(3-(thiophen-2-yl)allylamino)-2-morpholinobenzoate
  参考文献：
  名称：

  Synthesis and structure activity relationship studies of novel Staphylococcus aureus Sortase A inhibitors

  摘要：

  Synthetic methods have been developed for lead Sortase A inhibitors identified from previous studies. Several derivatives of the lead inhibitor were synthesized to derive preliminary structure activity relationships (SAR). Different regions of the lead inhibitor that are critical for the enzyme activity have been determined by systematic SAR studies. The E stereochemistry of the lead compound was found to be critical for its activity. Replacement of the E double bond with Z double bond or a rigid triple bond reduced the enzyme inhibitory activity in most cases. Reduction of the double bond to a C-C single bond resulted in complete loss of activity. Amide carbonyl and NH groups were also found to be crucial for the activity of this class of inhibitors, as well. The morpholine ring oxygen atom was also found to be an important factor for the activity of the lead inhibitor. Preliminary SAR studies led to the identification of compounds with improved enzyme inhibition. The most active compound was found to have an IC(50) value of 58 mu M against the enzyme. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.024