(2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxo-2-[[2-[(1R,2R,6R,7S,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]acetyl]amino]pentanoic acid | 418771-12-7

• 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: (2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxo-2-[[2-[(1R,2R,6R,7S,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]acetyl]amino]pentanoic acid
• CAS: 418771-12-7
• 化学式: C₂₃H₃₇NO₁₀
• 分子量: 487.547
• InChiKey: XNOIZXXCJCXTOS-OXEQCJSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxo-2-[[2-[(1R,2R,6R,7S,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]acetyl]amino]pentanoic acid 在 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (4S)-5-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-5-oxo-4-[[2-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetyl]amino]pentanoic acid
  参考文献：
  名称：

  β-C-Mannosides as Selectin Inhibitors

  摘要：

  Potential E- and P-selectin inhibitors were synthesized to explore a hydrophobic area on the E-selectin surface and the PSGL-1 protein binding site on the P-selectin surface that was recently defined by crystallography. Three series of mannose-based compounds (libraries A, B, and C) were synthesized using solution phase parallel synthesis. Biological evaluation of these compounds was done using two ELISA-based assays and transferred NOE (trNOE) experiments. Some of the compounds showed better activity than sLe(x) in the P-selectin assay.

  DOI：

  10.1021/jm010390f
• 作为产物：
  描述：

  (S)-5-叔丁基1-甲基2-氨基戊二酸酯 在 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 (2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxo-2-[[2-[(1R,2R,6R,7S,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]acetyl]amino]pentanoic acid
  参考文献：
  名称：

  β-C-Mannosides as Selectin Inhibitors

  摘要：

  Potential E- and P-selectin inhibitors were synthesized to explore a hydrophobic area on the E-selectin surface and the PSGL-1 protein binding site on the P-selectin surface that was recently defined by crystallography. Three series of mannose-based compounds (libraries A, B, and C) were synthesized using solution phase parallel synthesis. Biological evaluation of these compounds was done using two ELISA-based assays and transferred NOE (trNOE) experiments. Some of the compounds showed better activity than sLe(x) in the P-selectin assay.

  DOI：

  10.1021/jm010390f

文献信息

• β-C-Mannosides as Selectin Inhibitors
  作者：Neelu Kaila、Lihren Chen、Thomas、Desiree Tsao、Steve Tam、Patricia W. Bedard、Raymond T. Camphausen、Juan C. Alvarez、Giliyar Ullas

  DOI：10.1021/jm010390f

  日期：2002.4.1

  Potential E- and P-selectin inhibitors were synthesized to explore a hydrophobic area on the E-selectin surface and the PSGL-1 protein binding site on the P-selectin surface that was recently defined by crystallography. Three series of mannose-based compounds (libraries A, B, and C) were synthesized using solution phase parallel synthesis. Biological evaluation of these compounds was done using two ELISA-based assays and transferred NOE (trNOE) experiments. Some of the compounds showed better activity than sLe(x) in the P-selectin assay.