dimethyl 4-[N-[6-(3,5-didecoxyphenoxy)hexanoyl]-4-methoxycarbonylanilino]benzene-1,2-dicarboxylate | 875211-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 4-[N-[6-(3,5-didecoxyphenoxy)hexanoyl]-4-methoxycarbonylanilino]benzene-1,2-dicarboxylate
• CAS: 875211-06-6
• 化学式: C₅₀H₇₁NO₁₀
• 分子量: 846.114
• InChiKey: IWYHMCCJFLLNCW-UHFFFAOYSA-N

物化性质

• 沸点：
  894.6±65.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  61
• 可旋转键数：
  35
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dimethyl 4-[N-[6-(3,5-didecoxyphenoxy)hexanoyl]-4-methoxycarbonylanilino]benzene-1,2-dicarboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以71%的产率得到4-[4-carboxy-N-[6-(3,5-didecoxyphenoxy)hexanoyl]anilino]phthalic acid
  参考文献：
  名称：

  A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors

  摘要：

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.

  DOI：

  10.1021/jm060468y
• 作为产物：
  描述：

  4-氨基苯-1,2-二羧酸二乙酯 在 copper(l) iodide 、 四丁基碘化铵 、 铜 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 二丁醚 、 环己酮 为溶剂， 反应 109.5h， 生成 dimethyl 4-[N-[6-(3,5-didecoxyphenoxy)hexanoyl]-4-methoxycarbonylanilino]benzene-1,2-dicarboxylate
  参考文献：
  名称：

  A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors

  摘要：

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.

  DOI：

  10.1021/jm060468y

文献信息

• A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors
  作者：Holger K. Ulbrich、Andreas Luxenburger、Philip Prech、Einar E. Eriksson、Oliver Soehnlein、Pierre Rotzius、Lennart Lindbom、Gerd Dannhardt

  DOI：10.1021/jm060468y

  日期：2006.10.1

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.