(2,5-Dioxopyrrolidin-1-yl) 2-[2-[2-[2-[2-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate | 211746-83-7

• 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: (2,5-Dioxopyrrolidin-1-yl) 2-[2-[2-[2-[2-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate
• CAS: 211746-83-7
• 化学式: C₂₀H₂₈N₂O₁₃
• 分子量: 504.448
• InChiKey: WBXKDGLANLVUCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  615.0±65.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  174
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2,5-Dioxopyrrolidin-1-yl) 2-[2-[2-[2-[2-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate 、 5-{[(2-aminoethyl)amino]carbonyl}pentyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以20%的产率得到
  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：

  di-tert-butyl 3,6,9,12,15-pentaoxaheptadecanedioate 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2,5-Dioxopyrrolidin-1-yl) 2-[2-[2-[2-[2-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate
  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

文献信息

• Ligand Recognition by E- and P-Selectin:  Chemoenzymatic Synthesis and Inhibitory Activity of Bivalent Sialyl Lewis x Derivatives and Sialyl Lewis x Carboxylic Acids
  作者：Valentin Wittmann、Shuichi Takayama、Ke Wei Gong、Gabriele Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1021/jo980350s

  日期：1998.7.1

  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.