{(1R,3R,4R,5S)-4-[(2,3,4-tris-O-benzyl-6-deoxy-α-L-galactopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2,4,6-tri-O-benzoyl-3-O-[(1S)-1-benzyloxycarbonyl-2-cyclohexylethyl]-β-D-galactopyranoside | 1026073-54-0

• 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: {(1R,3R,4R,5S)-4-[(2,3,4-tris-O-benzyl-6-deoxy-α-L-galactopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2,4,6-tri-O-benzoyl-3-O-[(1S)-1-benzyloxycarbonyl-2-cyclohexylethyl]-β-D-galactopyranoside
• CAS: 1026073-54-0
• 化学式: C₇₉H₈₆O₁₈
• 分子量: 1323.54
• InChiKey: XHQDFPDLHCNNTN-LIAIQJICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.98
• 重原子数：
  97.0
• 可旋转键数：
  28.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  205.34
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  {(1R,3R,4R,5S)-4-[(2,3,4-tris-O-benzyl-6-deoxy-α-L-galactopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2,4,6-tri-O-benzoyl-3-O-[(1S)-1-benzyloxycarbonyl-2-cyclohexylethyl]-β-D-galactopyranoside 在 palladium hydroxide on carbon 氢气 、 甲醇 、 sodium methylate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 甲醇 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 62.0h， 以76%的产率得到{(1R,3R,4R,5S)-4-[(α-L-fucopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2-O-benzoyl-3-O-[(1S)-1-carboxy-2-cyclohexylethyl]-β-D-galactopyranoside
  参考文献：
  名称：

  Glycomimetic replacements for hexoses and N-acetyl hexosamines

  摘要：

  提供了一种获取寡糖类模拟物的化合物和方法。更具体地，描述了一种通过在环己烷衍生物中合并或替代来获得寡糖类模拟物的化合物和方法。

  公开号：

  US20080161546A1
• 作为产物：
  描述：

  methyl (1R,3R,4R,5S)-4-O-(2,3,4-tris-O-benzyl-6-deoxy-α-L-galactopyranosyl)-3,4-dihydroxy-5-methylcyclohexane-1-carboxylate 、 ethyl 3-O-[(1S)-1-(cyclohexylmethyl)-2-oxo-2-(phenylmethoxy)ethyl]-1-thio-β-D-galactopyranoside 2,4,6-tribenzoate 在 dimethyl(methylthio)sulfonium triflate 作用下， 以 二氯甲烷 为溶剂， 反应 67.0h， 以66%的产率得到{(1R,3R,4R,5S)-4-[(2,3,4-tris-O-benzyl-6-deoxy-α-L-galactopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2,4,6-tri-O-benzoyl-3-O-[(1S)-1-benzyloxycarbonyl-2-cyclohexylethyl]-β-D-galactopyranoside
  参考文献：
  名称：

  Methods of use of glycomimetics with replacements for hexoses and n-acetyl hexosamines

  摘要：

  提供了一种使用化合物治疗内皮功能障碍，包括血管异常的方法。更具体地，描述了使用寡糖化合物或糖类模拟化合物的方法，其中环己烷衍生物被合并在其中。

  公开号：

  US20080200406A1

文献信息

• [EN] HETEROBIFUNCTIONAL INHIBITORS OF E-SELECTINS AND CXCR4 CHEMOKINE RECEPTORS<br/>[FR] INHIBITEURS HÉTÉROBIFONCTIONNELS D'E-SÉLECTINES ET DE RÉCEPTEURS AUX CHIMIOKINES CXCR4
  申请人：GLYCOMIMETICS INC

  公开号：WO2010126888A1

  公开（公告）日：2010-11-04

  Compounds, compositions and methods are provided for treating cancer and inflammatory diseases, and for releasing cells such as stem cells (e.g., bone marrow progenitor cells) into circulating blood and enhancing retention of the cells in the blood. More specifically, heterobifunctional compounds that inhibit both E-selectins and CXCR4 chemokine receptors are described.

  提供了用于治疗癌症和炎症性疾病的化合物、组合物和方法，以及释放细胞（如干细胞，例如骨髓祖细胞）进入循环血液并增强细胞在血液中的保留。具体描述了同时抑制E-选择素和CXCR4趋化受体的异二功能化合物。
• Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach
  作者：Jonas Egger、Céline Weckerle、Brian Cutting、Oliver Schwardt、Said Rabbani、Katrin Lemme、Beat Ernst

  DOI：10.1021/ja4029582

  日期：2013.7.3

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.
• [EN] GLYCOMIMETIC-PEPTIDOMIMETIC INHIBITORS OF E-SELECTINS AND CXCR4 CHEMOKINE RECEPTORS<br/>[FR] INHIBITEURS GLYCOMIMÉTIQUES-PEPTIDOMIMÉTIQUES DE SÉLECTINES E ET DE RÉCEPTEURS DE CHIMIOKINE CXCR4
  申请人：GLYCOMIMETICS INC

  公开号：WO2012061662A9

  公开（公告）日：2012-12-06