2-(adamantan-1-yl)-N-(2-(4-(5-amino-2-((4-ethynylbenzyl)oxy)benzyl)piperazin-1-yl)-2-oxoethyl)acetamide | 1422430-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(adamantan-1-yl)-N-(2-(4-(5-amino-2-((4-ethynylbenzyl)oxy)benzyl)piperazin-1-yl)-2-oxoethyl)acetamide
• CAS: 1422430-40-7
• 化学式: C₃₄H₄₂N₄O₃
• 分子量: 554.732
• InChiKey: BQIAIRCIZYSSCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.9
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(adamantan-1-yl)-N-(2-(4-(5-amino-2-((4-ethynylbenzyl)oxy)benzyl)piperazin-1-yl)-2-oxoethyl)acetamide 在 盐酸 、 sodium nitrite 、 sodium azide 、 sodium acetate 作用下， 以 水 为溶剂， 反应 4.25h， 以5 mg的产率得到2-((3r,5r,7r)-adamantan-1-yl)-N-(2-(4-(5-azido-2-((4-ethynylbenzyl)oxy)benzyl)piperazin-1-yl)-2-oxoethyl)acetamide
  参考文献：
  名称：

  Inhibition of Ebola Virus Infection: Identification of Niemann-Pick C1 as the Target by Optimization of a Chemical Probe

  摘要：

  A high-throughput screen identified adamantane dipeptide 1 as an inhibitor of Ebola virus (EboV) infection. Hit-to-lead optimization to determine the structure-activity relationship (SAR) identified the more potent EboV inhibitor 2 and a photoaffinity labeling agent 3. These antiviral compounds were employed to identify the target as Niemann-Pick C1 (NPC1), a host protein that binds the EboV glycoprotein and is essential for infection. These studies establish NPC1 as a promising target for antiviral therapy.

  DOI：

  10.1021/ml300370k
• 作为产物：
  描述：

  2-(adamantan-1-yl)-N-(2-(4-(2-((4-ethynylbenzyl)oxy)-5-nitrobenzyl)piperazin-1-yl)-2-oxoethyl)acetamide 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以46 mg的产率得到2-(adamantan-1-yl)-N-(2-(4-(5-amino-2-((4-ethynylbenzyl)oxy)benzyl)piperazin-1-yl)-2-oxoethyl)acetamide
  参考文献：
  名称：

  Inhibition of Ebola Virus Infection: Identification of Niemann-Pick C1 as the Target by Optimization of a Chemical Probe

  摘要：

  A high-throughput screen identified adamantane dipeptide 1 as an inhibitor of Ebola virus (EboV) infection. Hit-to-lead optimization to determine the structure-activity relationship (SAR) identified the more potent EboV inhibitor 2 and a photoaffinity labeling agent 3. These antiviral compounds were employed to identify the target as Niemann-Pick C1 (NPC1), a host protein that binds the EboV glycoprotein and is essential for infection. These studies establish NPC1 as a promising target for antiviral therapy.

  DOI：

  10.1021/ml300370k

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF EBOLA AND LASSA FEVER VIRUSES<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DES VIRUS ÉBOLA ET DE LA FIÈVRE DE LASSA
  申请人：HARVARD COLLEGE

  公开号：WO2013022550A3

  公开（公告）日：2013-04-25