tert-butyl (2-cyanoethyl)(3-hydroxypropyl)carbamate | 1160936-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (2-cyanoethyl)(3-hydroxypropyl)carbamate
• CAS: 1160936-39-9
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: KAFIWVLZIMAYCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  73.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-cyanoethyl)(3-hydroxypropyl)carbamate 、 1,5-双-叔丁氧羰基-1,5,9-里亚萨壬 在 Pearlman catalyst 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 tert-butyl (3-((3-((tert-butoxycarbonyl)(3-hydroxypropyl)amino)propyl)amino)propyl)(3-((tert-butoxycarbonyl)amino)propyl)carbamate
  参考文献：
  名称：

  Structure–activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines

  摘要：

  We have previously shown that simple N-acyl or N-alkyl polyamines bind to and sequester Gram-negative bacterial lipopolysaccharide, affording protection against lethality in animal models of endotoxicosis. Several iterative design-and-test cycles of SAR studies, including high-throughput screens, had converged on compounds with polyamine scaffolds which have been investigated extensively with reference to the number, position, and length of acyl or alkyl appendages. However, the polyamine backbone itself had not been explored sufficiently, and it was not known if incremental variations on the polymethylene spacing would affect LPS-binding and neutralization properties. We have now systematically explored the relationship between variously elongated spermidine [NH2-(CH2)(3)-NH-(CH2)(4)-NH2] and norspermidine [NH2-(CH2)(3)-NH-(CH2)(3)-NH2] backbones, with the N-alkyl group being held constant at C-16 in order to examine if changing the spacing between the inner secondary amines may yield additional SAR information. We find that the norspermine-type compounds consistently showed higher activity compared to corresponding spermine homologues. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.055
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 3-(3-羟基丙基氨基)丙腈 以 甲醇 为溶剂， 反应 24.0h， 以5 g的产率得到tert-butyl (2-cyanoethyl)(3-hydroxypropyl)carbamate
  参考文献：
  名称：

  Structure–activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines

  摘要：

  We have previously shown that simple N-acyl or N-alkyl polyamines bind to and sequester Gram-negative bacterial lipopolysaccharide, affording protection against lethality in animal models of endotoxicosis. Several iterative design-and-test cycles of SAR studies, including high-throughput screens, had converged on compounds with polyamine scaffolds which have been investigated extensively with reference to the number, position, and length of acyl or alkyl appendages. However, the polyamine backbone itself had not been explored sufficiently, and it was not known if incremental variations on the polymethylene spacing would affect LPS-binding and neutralization properties. We have now systematically explored the relationship between variously elongated spermidine [NH2-(CH2)(3)-NH-(CH2)(4)-NH2] and norspermidine [NH2-(CH2)(3)-NH-(CH2)(3)-NH2] backbones, with the N-alkyl group being held constant at C-16 in order to examine if changing the spacing between the inner secondary amines may yield additional SAR information. We find that the norspermine-type compounds consistently showed higher activity compared to corresponding spermine homologues. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.055