tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-(2-(N-hexadecylcarbamimidoyl)hydrazineylidene)propyl)amino)propyl)carbamate | 1134204-38-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-(2-(N-hexadecylcarbamimidoyl)hydrazineylidene)propyl)amino)propyl)carbamate
• CAS: 1134204-38-8
• 化学式: C₅₀H₉₈N₈O₈
• 分子量: 939.377
• InChiKey: VPNRGHIPJWEIAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.75
• 重原子数：
  66.0
• 可旋转键数：
  32.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  187.22
• 氢给体数：
  4.0
• 氢受体数：
  10.0

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-(2-(N-hexadecylcarbamimidoyl)hydrazineylidene)propyl)amino)propyl)carbamate 、 三氟乙酸 反应 0.5h， 以100%的产率得到1-[3-[3-[4-(3-aminopropylamino)butylamino]propylamino]propylideneamino]-2-hexadecylguanidine;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Structure–activity relationships of lipopolysaccharide sequestration in guanylhydrazone-bearing lipopolyamines

  摘要：

  The toxicity of Gram-negative bacterial endotoxin (lipopolysaccharide, LPS) resides in its structurally highly conserved glycolipid component called lipid A. Our major goal has been to develop small-molecules that would sequester LPS by binding to the lipid A moiety, so that it could be useful for the prophylaxis or adjunctive therapy of Gram-negative sepsis. We had previously identified in rapid-throughput screens several guanylhydrazones as potent LPS binders. We were desirous of examining if the presence of the guanylhydrazone (rather than an amine) functionality would afford greater LPS sequestration potency. In evaluating a congeneric set of guanylhydrazone analogues, we find that C-16 alkyl substitution is optimal in the N-alkylguanylhydrazone series; a homospermine analogue with the terminal amine N-alkylated with a C-16 chain with the other terminus of the molecule bearing an unsubstituted guanylhydrazone moiety is marginally more active, suggesting very slight, if any, steric effects. Neither C-16 analogue is significantly more active, than the N-C-16-alkyl or N-C-16-acyl compounds that we had characterized earlier, indicating that basicity of the phosphate-recognizing cationic group, is not a determinant of LPS sequestration activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.051
• 作为产物：
  描述：

  1-Amino-2-hexadecylguanidine;hydroiodide 、 tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-oxopropyl)amino)propyl)carbamate 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以71%的产率得到tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-((tert-butoxycarbonyl)(3-(2-(N-hexadecylcarbamimidoyl)hydrazineylidene)propyl)amino)propyl)carbamate
  参考文献：
  名称：

  Structure–activity relationships of lipopolysaccharide sequestration in guanylhydrazone-bearing lipopolyamines

  摘要：

  The toxicity of Gram-negative bacterial endotoxin (lipopolysaccharide, LPS) resides in its structurally highly conserved glycolipid component called lipid A. Our major goal has been to develop small-molecules that would sequester LPS by binding to the lipid A moiety, so that it could be useful for the prophylaxis or adjunctive therapy of Gram-negative sepsis. We had previously identified in rapid-throughput screens several guanylhydrazones as potent LPS binders. We were desirous of examining if the presence of the guanylhydrazone (rather than an amine) functionality would afford greater LPS sequestration potency. In evaluating a congeneric set of guanylhydrazone analogues, we find that C-16 alkyl substitution is optimal in the N-alkylguanylhydrazone series; a homospermine analogue with the terminal amine N-alkylated with a C-16 chain with the other terminus of the molecule bearing an unsubstituted guanylhydrazone moiety is marginally more active, suggesting very slight, if any, steric effects. Neither C-16 analogue is significantly more active, than the N-C-16-alkyl or N-C-16-acyl compounds that we had characterized earlier, indicating that basicity of the phosphate-recognizing cationic group, is not a determinant of LPS sequestration activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.051