N-[2-oxo-2-(4-{4-[2-(1-pyrrolidinyl)acetylamino]benzyl}phenylamino)ethyl]carbamic acid 1,1-dimethylethyl ester | 1283594-54-6

• 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: N-[2-oxo-2-(4-{4-[2-(1-pyrrolidinyl)acetylamino]benzyl}phenylamino)ethyl]carbamic acid 1,1-dimethylethyl ester
• CAS: 1283594-54-6
• 化学式: C₂₆H₃₄N₄O₄
• 分子量: 466.58
• InChiKey: OJHLOIXSBAXYDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  99.77
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[2-oxo-2-(4-{4-[2-(1-pyrrolidinyl)acetylamino]benzyl}phenylamino)ethyl]carbamic acid 1,1-dimethylethyl ester 在 盐酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以87%的产率得到N-(4-{4-[(2-aminoacetyl)amino]benzyl}phenyl)-2-(1-pyrrolidinyl)acetamide
  参考文献：
  名称：

  Synthesis of GN8 derivatives and evaluation of their antiprion activity in TSE-infected cells

  摘要：

  A series of GN8 derivatives were synthesized from various diamines, carboxylic acid derivatives, and nitrogen nucleophiles, and their antiprion activity was tested in TSE-infected mouse neuronal cells. We found that two ethylenediamine units, hydrophobic substituents on the nitrogen atoms, and the diphenylmethane scaffold were essential structural features responsible for the activity. Seven derivatives bearing substituents at the benzylic position exhibited an improved antiprion activity with the IC50 values of 0.51-0.83 mu M. Conformational analysis of model compounds suggested that the introduction of the substituent at the benzylic position restricted the conformational variability of the diphenylmethane unit. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.132
• 作为产物：
  描述：

  N-{4-[4-(2-bromoacetylamino)benzyl]phenyl}carbamic acid 1,1-dimethylethyl ester 在 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 N-[2-oxo-2-(4-{4-[2-(1-pyrrolidinyl)acetylamino]benzyl}phenylamino)ethyl]carbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis of GN8 derivatives and evaluation of their antiprion activity in TSE-infected cells

  摘要：

  A series of GN8 derivatives were synthesized from various diamines, carboxylic acid derivatives, and nitrogen nucleophiles, and their antiprion activity was tested in TSE-infected mouse neuronal cells. We found that two ethylenediamine units, hydrophobic substituents on the nitrogen atoms, and the diphenylmethane scaffold were essential structural features responsible for the activity. Seven derivatives bearing substituents at the benzylic position exhibited an improved antiprion activity with the IC50 values of 0.51-0.83 mu M. Conformational analysis of model compounds suggested that the introduction of the substituent at the benzylic position restricted the conformational variability of the diphenylmethane unit. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.132