(2S,4S,5S,7S)-5-azido-N-(3-(3,3-dimethylureido)-2,2-dimethylpropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide | 1321622-52-9

• 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: (2S,4S,5S,7S)-5-azido-N-(3-(3,3-dimethylureido)-2,2-dimethylpropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide
• 英文别名: (2S,4S,5S,7S)-5-azido-N-[3-(dimethylcarbamoylamino)-2,2-dimethylpropyl]-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide
• CAS: 1321622-52-9
• 化学式: C₃₃H₅₈N₆O₆
• 分子量: 634.86
• InChiKey: UTMZYTAQWPTXQN-LJWNLINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  45
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S,7S)-5-azido-N-(3-(3,3-dimethylureido)-2,2-dimethylpropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide 在 palladium 10% on activated carbon 、 氢气 、 C.I.酸性橙108 作用下， 以 甲基叔丁基醚 为溶剂， 以89.6%的产率得到(2S,4S,5S,7S)-5-amino-N-(3-(3,3-dimethylureido)-2,2-dimethylpropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide
  参考文献：
  名称：

  Synthesis, biological evaluation and docking studies of octane-carboxamide based renin inhibitors with extended segments toward S3′ site of renin

  摘要：

  Eighteen octane-carboxamide based renin inhibitors with extended segments for mimicking P3' unit of angiotensinogen have been synthesized. The biological evaluation identified novel renin inhibitors with more potent activity than aliskiren. Molecular docking studies showed that the extended amide-tails matched the P3' position of angiotensinogen and exerted interactions with the S3' site of renin. An unexpected pi-pi stacking interaction was observed during docking study for compound 9r, which could be a reasonable explanation for the outstanding potency of this compound. Further study is in progress to reveal a feasibility for developing novel renin inhibitors based on the possible non-classical interactions between the ligands and the new subsite of renin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.059
• 作为产物：
  描述：

  二溴新戊烷 在 2-羟基吡啶 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (2S,4S,5S,7S)-5-azido-N-(3-(3,3-dimethylureido)-2,2-dimethylpropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide
  参考文献：
  名称：

  Synthesis, biological evaluation and docking studies of octane-carboxamide based renin inhibitors with extended segments toward S3′ site of renin

  摘要：

  Eighteen octane-carboxamide based renin inhibitors with extended segments for mimicking P3' unit of angiotensinogen have been synthesized. The biological evaluation identified novel renin inhibitors with more potent activity than aliskiren. Molecular docking studies showed that the extended amide-tails matched the P3' position of angiotensinogen and exerted interactions with the S3' site of renin. An unexpected pi-pi stacking interaction was observed during docking study for compound 9r, which could be a reasonable explanation for the outstanding potency of this compound. Further study is in progress to reveal a feasibility for developing novel renin inhibitors based on the possible non-classical interactions between the ligands and the new subsite of renin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.059