1-(4-([1,1'-biphenyl]-4-ylmethoxy)phenyl)-2-bromoethan-1-one | 1159499-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-([1,1'-biphenyl]-4-ylmethoxy)phenyl)-2-bromoethan-1-one
• CAS: 1159499-95-2
• 化学式: C₂₁H₁₇BrO₂
• 分子量: 381.269
• InChiKey: IODHWUXPVSKOCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  521.8±40.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-([1,1'-biphenyl]-4-ylmethoxy)phenyl)-2-bromoethan-1-one 、 N-BOC-2-甲基-L-丝氨酸 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and evaluation of arylalkoxy- and biarylalkoxy-phenylamide and phenylimidazoles as potent and selective sphingosine-1-phosphate receptor subtype-1 agonists

  摘要：

  In pursuit of potent and selective sphingosine-1-phosphate receptor agonists, we have utilized previously reported phenylamide and phenylimidazole scaffolds to explore extensive side-chain modi. cations to generate new molecular entities. A number of designed molecules demonstrate good selectivity and excellent in vitro and in vivo potency in both mouse and rat models. Oral administration of the lead molecule 11c (PPI-4667) demonstrated potent and dose-responsive lymphopenia. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.073
• 作为产物：
  描述：

  1-[4-[(4-Phenylphenyl)methoxy]phenyl]ethanone 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 生成 1-(4-([1,1'-biphenyl]-4-ylmethoxy)phenyl)-2-bromoethan-1-one
  参考文献：
  名称：

  Synthesis and evaluation of arylalkoxy- and biarylalkoxy-phenylamide and phenylimidazoles as potent and selective sphingosine-1-phosphate receptor subtype-1 agonists

  摘要：

  In pursuit of potent and selective sphingosine-1-phosphate receptor agonists, we have utilized previously reported phenylamide and phenylimidazole scaffolds to explore extensive side-chain modi. cations to generate new molecular entities. A number of designed molecules demonstrate good selectivity and excellent in vitro and in vivo potency in both mouse and rat models. Oral administration of the lead molecule 11c (PPI-4667) demonstrated potent and dose-responsive lymphopenia. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.073

文献信息

• Exploration of amino alcohol derivatives as novel, potent, and highly selective sphingosine-1-phosphate receptor subtype-1 agonists
  作者：Ghotas Evindar、Sylvie G. Bernier、Elisabeth Doyle、Malcolm J. Kavarana、Alexander L. Satz、Jeanine Lorusso、Heather S. Blanchette、Ashis K. Saha、Gerhard Hannig、Barry A. Morgan、William F. Westlin

  DOI：10.1016/j.bmcl.2010.02.098

  日期：2010.4

  In pursuit of a potent and highly selective sphingosine-1-phosphate receptor agonists with an improved in vivo conversion of the precursor to the active phospho-drug, we have utilized previously reported phenylamide and phenylimidazole scaffolds to identify a selectivity enhancing moiety (SEM) and selectivity enhancing orientation (SEO) within both pharmacophores. SEM and SEO have allowed for over 100 to 500-fold improvement in selectivity for S1P receptor subtype 1 over subtype 3. Utility of SEM and SEO and further SAR study allowed for discovery of a potent and selective preclinical candidate PPI-4955 (21b) with an excellent in vivo potency and dose responsiveness and markedly improved overall in vivo pharmacodynamic properties upon oral administration. (C) 2010 Elsevier Ltd. All rights reserved.