8-(4-bromobenzyloxy)-3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,9-dione | 859224-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 8-(4-bromobenzyloxy)-3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,9-dione
• 英文别名: 8-(4-bromobenzyloxy)-3,5,10-trioxatricyclo[6.2.1.0^2,6]undecane-4,9-dione
• CAS: 859224-76-3
• 化学式: C₁₅H₁₃BrO₆
• 分子量: 369.169
• InChiKey: DTQQZVZHZZLKFM-MCYUEQNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  8-(4-bromobenzyloxy)-3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,9-dione 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Quinic Acid Derivatives as Sialyl Lewis^x-Mimicking Selectin Inhibitors:  Design, Synthesis, and Crystal Structure in Complex with E-Selectin

  摘要：

  A search for noncarbohydrate sLe(x) mimics led to the development of quinic acid derivatives as selectin inhibitors. At Wyeth we solved the first cocrystal structure of a small molecule, quinic acid, with E-selectin. In the cocomplex two hydroxyls of quinic acid mimic the calcium-bound fucose of the tetrasaccharide sLe(x). The X-ray structure, together with structure based computational methods, was used to design quinic acid based libraries that were synthesized and evaluated for their ability to block the interaction of sLex with P-selectin. A large number of analogues were prepared using solution-phase parallel synthesis. Selected compounds showed decrease in leukocyte rolling in the IVM mouse model. Compound 2 inhibited neutrophil influx in the murine TIP model and demonstrated good plasma exposure.

  DOI：

  10.1021/jm050049l
• 作为产物：
  描述：

  1,5-quinide 在 吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 8-(4-bromobenzyloxy)-3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,9-dione
  参考文献：
  名称：

  Quinic Acid Derivatives as Sialyl Lewis^x-Mimicking Selectin Inhibitors:  Design, Synthesis, and Crystal Structure in Complex with E-Selectin

  摘要：

  A search for noncarbohydrate sLe(x) mimics led to the development of quinic acid derivatives as selectin inhibitors. At Wyeth we solved the first cocrystal structure of a small molecule, quinic acid, with E-selectin. In the cocomplex two hydroxyls of quinic acid mimic the calcium-bound fucose of the tetrasaccharide sLe(x). The X-ray structure, together with structure based computational methods, was used to design quinic acid based libraries that were synthesized and evaluated for their ability to block the interaction of sLex with P-selectin. A large number of analogues were prepared using solution-phase parallel synthesis. Selected compounds showed decrease in leukocyte rolling in the IVM mouse model. Compound 2 inhibited neutrophil influx in the murine TIP model and demonstrated good plasma exposure.

  DOI：

  10.1021/jm050049l