Methyl 2,2-bis[(3,5-ditert-butylphenyl)methyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 1202779-16-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Methyl 2,2-bis[(3,5-ditert-butylphenyl)methyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1202779-16-5
• 化学式: C₃₉H₆₁NO₄
• 分子量: 607.918
• InChiKey: JBFBKBUPGYNWOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2,2-bis[(3,5-ditert-butylphenyl)methyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 lithium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以23%的产率得到2,2-Bis[(3,5-ditert-butylphenyl)methyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  参考文献：
  名称：

  Antimicrobial Activity of Small β-Peptidomimetics Based on the Pharmacophore Model of Short Cationic Antimicrobial Peptides

  摘要：

  We have synthesized a series of small beta-peptidomimetics (M-w < 650) that were based on the minimal pharmacophore model for anti-Staphylococcal activity of short cationic antimicrobial peptides. All beta-peptidomimetics had a net charge of +2 and formed an amphipathic scaffold consisting of an achiral lipophilic beta(2,2)-amino acid coupled to a C-terminal L-arginine amide residue. By varying the lipophilic side-chains of the beta(2,2)-amino acids, we obtained a series of highly potent beta-peptidomimetics with high enzymatic stability against alpha-chymotrypsin and a general low toxicity against human erythrocytes. The most potent beta-peptidomimetics displayed minimal inhibitory concentrations of 2.1-7.2 mu M against Staphylococcus aureus, methicillin resistant Staphylococcus aureus (MRSA), methicillin resistant Staphylococcus epidermidis (MRSE), and Escherichia coli, Small amphipathic beta-peptidomimetics may be a promising class of antimicrobial agents by means of having a similar range of potency and selectivity as larger cationic antimicrobial peptides in addition to improved enzymatic stability and lower costs of production.

  DOI：

  10.1021/jm901052r
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 C₃₄H₅₃NO₂ 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以60%的产率得到Methyl 2,2-bis[(3,5-ditert-butylphenyl)methyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Antimicrobial Activity of Small β-Peptidomimetics Based on the Pharmacophore Model of Short Cationic Antimicrobial Peptides

  摘要：

  We have synthesized a series of small beta-peptidomimetics (M-w < 650) that were based on the minimal pharmacophore model for anti-Staphylococcal activity of short cationic antimicrobial peptides. All beta-peptidomimetics had a net charge of +2 and formed an amphipathic scaffold consisting of an achiral lipophilic beta(2,2)-amino acid coupled to a C-terminal L-arginine amide residue. By varying the lipophilic side-chains of the beta(2,2)-amino acids, we obtained a series of highly potent beta-peptidomimetics with high enzymatic stability against alpha-chymotrypsin and a general low toxicity against human erythrocytes. The most potent beta-peptidomimetics displayed minimal inhibitory concentrations of 2.1-7.2 mu M against Staphylococcus aureus, methicillin resistant Staphylococcus aureus (MRSA), methicillin resistant Staphylococcus epidermidis (MRSE), and Escherichia coli, Small amphipathic beta-peptidomimetics may be a promising class of antimicrobial agents by means of having a similar range of potency and selectivity as larger cationic antimicrobial peptides in addition to improved enzymatic stability and lower costs of production.

  DOI：

  10.1021/jm901052r