2-[2-[2-[2-[2-[2-[2-(2-chloro-2-oxoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl chloride | 145815-81-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2-[2-[2-[2-[2-[2-[2-(2-chloro-2-oxoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl chloride
• CAS: 145815-81-2
• 化学式: C₁₆H₂₈Cl₂O₉
• 分子量: 435.299
• InChiKey: GLKCJQVKAVCBAK-UHFFFAOYSA-N

物化性质

• 沸点：
  485.7±40.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  27.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 2-[2-[2-[2-[2-[2-[2-(2-chloro-2-oxoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl chloride 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 七氧杂二十三烷二酸二(N-羟基琥珀酰亚胺)酯
  参考文献：
  名称：

  Ligand Recognition by E- and P-Selectin:  Chemoenzymatic Synthesis and Inhibitory Activity of Bivalent Sialyl Lewis x Derivatives and Sialyl Lewis x Carboxylic Acids

  摘要：

  Described is the preparation of five sLe(x) dimers and five sLe(x) carboxylic acids by coupling chemoenzymatically synthesized amino-substituted sialyl Lewis x (sLe(x)) derivative 4 to homobifunctional cross-linkers 20-24 of varying chain length. 20-24 were obtained by alkylating low-molecular-weight oligoethylene glycols with tert-butyl bromoacetate and subsequent transformation of the di-tert-butyl esters into disuccinimide esters. The products were assayed for inhibition against binding of a sLe(a)-polymer to immobilized E- and P-selectin. In the E-selectin assay all dimers had lower IC50 values than the sLex monomer. The results show that comparable binding enhancements can be obtained with linkers of completely different length and rigidity. In the P-selectin assay four of the five sLe(x) carboxylic acids displayed significantly improved inhibitory potency. The lowest IC50 value was observed for the compound with the shortest spacer between the sLex moiety and the additional carboxylate, being ca. 20-40 times more potent than unmodified sLex. These findings should be of importance for the design of new multivalent forms of sLe(x) as well as sLe(x) mimetics as high-affinity selectin ligands.

  DOI：

  10.1021/jo980350s
• 作为产物：
  描述：

  六甘醇 在 氢氧化钾 、 草酰氯 、 四丁基硫酸氢铵 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.67h， 生成 2-[2-[2-[2-[2-[2-[2-(2-chloro-2-oxoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl chloride
  参考文献：
  名称：

  Ligand Recognition by E- and P-Selectin:  Chemoenzymatic Synthesis and Inhibitory Activity of Bivalent Sialyl Lewis x Derivatives and Sialyl Lewis x Carboxylic Acids

  摘要：

  Described is the preparation of five sLe(x) dimers and five sLe(x) carboxylic acids by coupling chemoenzymatically synthesized amino-substituted sialyl Lewis x (sLe(x)) derivative 4 to homobifunctional cross-linkers 20-24 of varying chain length. 20-24 were obtained by alkylating low-molecular-weight oligoethylene glycols with tert-butyl bromoacetate and subsequent transformation of the di-tert-butyl esters into disuccinimide esters. The products were assayed for inhibition against binding of a sLe(a)-polymer to immobilized E- and P-selectin. In the E-selectin assay all dimers had lower IC50 values than the sLex monomer. The results show that comparable binding enhancements can be obtained with linkers of completely different length and rigidity. In the P-selectin assay four of the five sLe(x) carboxylic acids displayed significantly improved inhibitory potency. The lowest IC50 value was observed for the compound with the shortest spacer between the sLex moiety and the additional carboxylate, being ca. 20-40 times more potent than unmodified sLex. These findings should be of importance for the design of new multivalent forms of sLe(x) as well as sLe(x) mimetics as high-affinity selectin ligands.

  DOI：

  10.1021/jo980350s