4-[6-bromo-N-(4-(methoxycarbonyl)phenyl)hexaneamino]benzoic acid methyl ester | 912806-39-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[6-bromo-N-(4-(methoxycarbonyl)phenyl)hexaneamino]benzoic acid methyl ester
• 英文别名: methyl 4-[N-(6-bromohexyl)-4-methoxycarbonylanilino]benzoate
• CAS: 912806-39-4
• 化学式: C₂₂H₂₆BrNO₄
• 分子量: 448.357
• InChiKey: BDYCBSUOIIRPMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[6-bromo-N-(4-(methoxycarbonyl)phenyl)hexaneamino]benzoic acid methyl ester 在 lithium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 环己酮 为溶剂， 反应 29.0h， 生成 4-(N-6-(3,5-bis(decyloxy)phenoxy)hexyl)-N-(4-carboxylphenyl)benzoic 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-乙酰氨基苯甲酸甲酯 在 potassium phosphate 、 copper(l) iodide 、 硼烷四氢呋喃络合物 、 (1S,2S)-(+)-1,2-环己二胺 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二丁醚 为溶剂， 反应 13.5h， 生成 4-[6-bromo-N-(4-(methoxycarbonyl)phenyl)hexaneamino]benzoic acid methyl ester
  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.