methyl 2-(2-([1,1'-biphenyl]-4-yl)ethoxy)-5-(2-amino-3-hydroxy-2-methylpropanamido)benzoate | 1228319-31-0

• 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: methyl 2-(2-([1,1'-biphenyl]-4-yl)ethoxy)-5-(2-amino-3-hydroxy-2-methylpropanamido)benzoate
• CAS: 1228319-31-0
• 化学式: C₂₆H₂₈N₂O₅
• 分子量: 448.519
• InChiKey: ZBSVCRFBJROSKP-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  110.88
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-([1,1'-biphenyl]-4-yl)ethoxy)-5-(2-amino-3-hydroxy-2-methylpropanamido)benzoate 、 氯磷酸二乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Exploration of amino alcohol derivatives as novel, potent, and highly selective sphingosine-1-phosphate receptor subtype-1 agonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.02.098
• 作为产物：
  描述：

  tert-butyl (S)-2-(4-(4-phenylphenethyloxy)-3-(methoxyformyl)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-(2-([1,1'-biphenyl]-4-yl)ethoxy)-5-(2-amino-3-hydroxy-2-methylpropanamido)benzoate
  参考文献：
  名称：

  Exploration of amino alcohol derivatives as novel, potent, and highly selective sphingosine-1-phosphate receptor subtype-1 agonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.02.098