tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-(hexadecylamino)propyl)amino)propyl)carbamate | 946150-70-5

• 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: tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-(hexadecylamino)propyl)amino)propyl)carbamate
• CAS: 946150-70-5
• 化学式: C₄₉H₉₇N₅O₈
• 分子量: 884.338
• InChiKey: ILZGROGBZXQJPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.24
• 重原子数：
  62.0
• 可旋转键数：
  32.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  138.98
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-(hexadecylamino)propyl)amino)propyl)carbamate 、 三氟乙酸 反应 20.0h， 以88%的产率得到N¹-(3-aminopropyl)-N⁴-(3-(3-(hexadecylamino)propylamino)propyl)butane-1,4-diamine pentatrifluroacetate
  参考文献：
  名称：

  Protection from endotoxic shock by EVK-203, a novel alkylpolyamine sequestrant of lipopolysaccharide

  摘要：

  Lipopolysaccharides (LPS) play a key role in the pathogenesis of septic shock, a major cause of mortality in the critically ill patient. The only therapeutic option aimed at limiting downstream systemic inflammatory processes by targeting lipopolysaccharide is Toraymyxin (TM), an extracorporeal hemoperfusion device using solid phase-immobilized polymyxin B (PMB). While PMB is known to effectively sequester LPS, its severe systemic toxicity proscribes its parenteral use, and hemoperfusion may not be feasible in patients in shock. In our continuing efforts to develop small-molecule mimics which display the LPS-sequestering properties, but not the toxicity of PMB, a series of mono- and bis-substituted dialkylpolyamines were synthesized and evaluated. We show that EVK-203, an alkylpolyamine compound, specifically binds to and neutralizes the activity of LPS, and affords complete protection in a murine model of endotoxic shock. EVK-203 is without any apparent toxicity when administered to mice at multiples of therapeutic doses for several days. The specific endo toxin- sequestering property along with a very favorable therapeutic index renders this compound an ideal candidate for preclinical development. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.015
• 作为产物：
  描述：

  十六胺 、 2-(2-cyanoethyl)-6,11-bis<(1,1-dimethylethoxy)carbonyl>-2,6,11,15-tetraazahexadecanedioic acid bis(1,1-dimethylethyl) ester 在 palladium hydroxide on carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以87%的产率得到tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-(hexadecylamino)propyl)amino)propyl)carbamate
  参考文献：
  名称：

  Polyamines and their use as antibacterial and sensitizing agents

  摘要：

  多种链长的多胺被评估其抗微生物活性，以验证这些双阳离子两性化合物可能也结合并使革兰氏阴性细菌膜通透的假设。发现这些化合物具有显著的抗微生物活性，并通过细菌膜通透介导。经过烷基化的精胺，与C8或C9链双酰化，被发现能显著增加大肠杆菌对亲脂性抗生素如利福平的敏感性。

  公开号：

  US20070197658A1