4-{(1S,2R)-1-[(1S,2R)-1-(2-{2-[2-(2-Amino-ethoxy)-ethoxy]-ethoxy}-ethylcarbamoyl)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-2,3-dihydroxy-propylcarbamoyl}-butyric acid | 185753-17-7

• 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: 4-{(1S,2R)-1-[(1S,2R)-1-(2-{2-[2-(2-Amino-ethoxy)-ethoxy]-ethoxy}-ethylcarbamoyl)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-2,3-dihydroxy-propylcarbamoyl}-butyric acid
• CAS: 185753-17-7
• 化学式: C₂₇H₅₀N₄O₁₅
• 分子量: 670.712
• InChiKey: BBWNTKKTMMOVSJ-KJORSZOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.08
• 重原子数：
  46.0
• 可旋转键数：
  24.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  297.92
• 氢给体数：
  10.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N-succinimidyl 10,12-pentacosadiynoic acid ester 、 4-{(1S,2R)-1-[(1S,2R)-1-(2-{2-[2-(2-Amino-ethoxy)-ethoxy]-ethoxy}-ethylcarbamoyl)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-2,3-dihydroxy-propylcarbamoyl}-butyric acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以84%的产率得到
  参考文献：
  名称：

  Liposome-like fucopeptides as sialyl lewis X mimetics

  摘要：

  Several fucodipeptides and their liposome-like derivatives were prepared and tested as inhibitors of sialyl Lewis X binding to E-selectin. It has been found that trans-hydroxyproline (D or L) can be used to mimic the galactose residue of sialyl Lewis X, and the mimetic containing 3,4-dihydroxy-D-proline is the most active with IC50 value (50 mu M) 10-fold greater than sialyl Lewis X. Derivatization of a hydroxythreonine-containing fucodipeptides into a covalent liposome-like derivative, however, provides a mimetic with only IC50 similar to 30 mu M. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00509-4
• 作为产物：
  描述：

  4-{(1S,2R)-1-[(1S,2R)-1-(2-{2-[2-(2-Azido-ethoxy)-ethoxy]-ethoxy}-ethylcarbamoyl)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3-benzyloxy-2-hydroxy-propylcarbamoyl}-butyric acid benzyl ester 在 palladium dihydroxide 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 溶剂黄146 为溶剂， 以94%的产率得到4-{(1S,2R)-1-[(1S,2R)-1-(2-{2-[2-(2-Amino-ethoxy)-ethoxy]-ethoxy}-ethylcarbamoyl)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-2,3-dihydroxy-propylcarbamoyl}-butyric acid
  参考文献：
  名称：

  Liposome-like fucopeptides as sialyl lewis X mimetics

  摘要：

  Several fucodipeptides and their liposome-like derivatives were prepared and tested as inhibitors of sialyl Lewis X binding to E-selectin. It has been found that trans-hydroxyproline (D or L) can be used to mimic the galactose residue of sialyl Lewis X, and the mimetic containing 3,4-dihydroxy-D-proline is the most active with IC50 value (50 mu M) 10-fold greater than sialyl Lewis X. Derivatization of a hydroxythreonine-containing fucodipeptides into a covalent liposome-like derivative, however, provides a mimetic with only IC50 similar to 30 mu M. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00509-4