2-(8-aminooctanamido)-5-(3-aminopropoxy)-N-(4-(4-(benzyloxy)phenoxy)phenyl)benzamide | 1192471-22-9

• 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: 2-(8-aminooctanamido)-5-(3-aminopropoxy)-N-(4-(4-(benzyloxy)phenoxy)phenyl)benzamide
• CAS: 1192471-22-9
• 化学式: C₃₇H₄₄N₄O₅
• 分子量: 624.78
• InChiKey: LLVVKCZCZRTDDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  46.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  137.93
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(8-aminooctanamido)-5-(3-aminopropoxy)-N-(4-(4-(benzyloxy)phenoxy)phenyl)benzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.0h， 以74%的产率得到2-(8-aminooctanamido)-5-(3-aminopropoxy)-N-(4-(4-hydroxyphenoxy)phenyl)benzamide
  参考文献：
  名称：

  ω-Conotoxin GVIA mimetics based on an anthranilamide core: Effect of variation in ammonium side chain lengths and incorporation of fluorine

  摘要：

  A number of omega-conotoxin GVIA mimetics based on an anthranilamide core were prepared and tested for their affinity for rat brain Ca(v)2.2 channels. Features such as the presence of hydroxyl and fluoro substituents on the tyrosine side chain mimic, the length of the chains on the lysine/arginine side chain mimics and the use of diguanidino and diamino substituents rather than mono-guanidine/mono-amine substitution were examined. The diguanidinylated compounds proved to be the most active and deletion of the hydroxyl substituent had a limited influence on activity. The SAR associated with variation in the lysine/arginine side chain mimics was not strong. The introduction of a fluoro substituent into the tyrosine mimic produced the most active compound prepared in this study (2g), with an EC50 at rat brain Ca(v)2.2 channels of 6 mu M. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.063
• 作为产物：
  描述：

  2-(8-azidooctanamido)-5-(3-azidopropoxy)-N-(4-(4-(benzyloxy)phenoxy)phenyl)benzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到2-(8-aminooctanamido)-5-(3-aminopropoxy)-N-(4-(4-(benzyloxy)phenoxy)phenyl)benzamide
  参考文献：
  名称：

  ω-Conotoxin GVIA mimetics based on an anthranilamide core: Effect of variation in ammonium side chain lengths and incorporation of fluorine

  摘要：

  A number of omega-conotoxin GVIA mimetics based on an anthranilamide core were prepared and tested for their affinity for rat brain Ca(v)2.2 channels. Features such as the presence of hydroxyl and fluoro substituents on the tyrosine side chain mimic, the length of the chains on the lysine/arginine side chain mimics and the use of diguanidino and diamino substituents rather than mono-guanidine/mono-amine substitution were examined. The diguanidinylated compounds proved to be the most active and deletion of the hydroxyl substituent had a limited influence on activity. The SAR associated with variation in the lysine/arginine side chain mimics was not strong. The introduction of a fluoro substituent into the tyrosine mimic produced the most active compound prepared in this study (2g), with an EC50 at rat brain Ca(v)2.2 channels of 6 mu M. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.063