4-Bromo-1-(2-bromo-4-chlorophenoxymethyl)-2-fluorobenzene | 1281674-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Bromo-1-(2-bromo-4-chlorophenoxymethyl)-2-fluorobenzene
• 英文别名: 2-bromo-1-[(4-bromo-2-fluorophenyl)methoxy]-4-chlorobenzene
• CAS: 1281674-67-6
• 化学式: C₁₃H₈Br₂ClFO
• mdl: MFCD19444468
• 分子量: 394.465
• InChiKey: CGQIJWYTPVDCMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Bromo-1-(2-bromo-4-chlorophenoxymethyl)-2-fluorobenzene 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Discovery of GSK345931A: An EP1 receptor antagonist with efficacy in preclinical models of inflammatory pain

  摘要：

  Herein we describe the medicinal chemistry programme to identify a potential back-up compound to the EP1 receptor antagonist GW848687X. This work started with the lipophilic 1,2-biaryl benzene derivative 4 which displayed molecular weight of 414.9 g/mol and poor in vivo metabolic stability in the rat and resulted in the identification of compound 7i (GSK345931A) which demonstrated good metabolic stability in the rat and lower molecular weight (381.9 g/mol). In addition, 7i (GSK345931A) showed measurable CNS penetration in the mouse and rat and potent analgesic efficacy in acute and sub-chronic models of inflammatory pain. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.032
• 作为产物：
  描述：

  2-溴-4-氯苯酚 、 4-溴-2-氟苄溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-Bromo-1-(2-bromo-4-chlorophenoxymethyl)-2-fluorobenzene
  参考文献：
  名称：

  Discovery of GSK345931A: An EP1 receptor antagonist with efficacy in preclinical models of inflammatory pain

  摘要：

  Herein we describe the medicinal chemistry programme to identify a potential back-up compound to the EP1 receptor antagonist GW848687X. This work started with the lipophilic 1,2-biaryl benzene derivative 4 which displayed molecular weight of 414.9 g/mol and poor in vivo metabolic stability in the rat and resulted in the identification of compound 7i (GSK345931A) which demonstrated good metabolic stability in the rat and lower molecular weight (381.9 g/mol). In addition, 7i (GSK345931A) showed measurable CNS penetration in the mouse and rat and potent analgesic efficacy in acute and sub-chronic models of inflammatory pain. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.032

文献信息

• Discovery of GSK345931A: An EP1 receptor antagonist with efficacy in preclinical models of inflammatory pain
  作者：Adrian Hall、Susan H. Brown、Christopher Budd、Nicholas M. Clayton、Gerard M.P. Giblin、Paul Goldsmith、Thomas G. Hayhow、David N. Hurst、Alan Naylor、D. Anthony Rawlings、Tiziana Scoccitti、Alexander W. Wilson、Wendy J. Winchester

  DOI：10.1016/j.bmcl.2008.11.032

  日期：2009.1

  Herein we describe the medicinal chemistry programme to identify a potential back-up compound to the EP1 receptor antagonist GW848687X. This work started with the lipophilic 1,2-biaryl benzene derivative 4 which displayed molecular weight of 414.9 g/mol and poor in vivo metabolic stability in the rat and resulted in the identification of compound 7i (GSK345931A) which demonstrated good metabolic stability in the rat and lower molecular weight (381.9 g/mol). In addition, 7i (GSK345931A) showed measurable CNS penetration in the mouse and rat and potent analgesic efficacy in acute and sub-chronic models of inflammatory pain. (C) 2008 Elsevier Ltd. All rights reserved.