methyl (S)-2-((4-ethynylbenzyl)amino)-2-phenylacetate | 1198184-38-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-2-((4-ethynylbenzyl)amino)-2-phenylacetate
• CAS: 1198184-38-1
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: GURHETOICLPVHO-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-3-iodo-phenyl)-5-methanesulfonyl-1-(3-morpholin-4-yl-propyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine 、 methyl (S)-2-((4-ethynylbenzyl)amino)-2-phenylacetate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 Methyl (2S)-({[4-({2-chloro-5-[5-(methylsulfonyl)-1-(3-morpholin-4-ylpropyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]phenyl}ethynyl)phenyl]methyl]amino)(phenyl)ethanoate
  参考文献：
  名称：

  Pyrazole-based arylalkyne cathepsin S inhibitors. Part II: Optimization of cellular potency

  摘要：

  Basic lipophilic substituents dramatically improved the cellular potency of a previously disclosed series of pyrazole-based arylalkyne cathepsin S inhibitors. The incorporation of substituted benzylamines in the para position of the arylalkyne maintained enzymatic activity (hCatS IC(50) = 80-420 nM) and imparted cellular potency (IC(50) = 0.8-4.0 mu M). Further refinement of the morpholine portion of the pharmacophore enabled the identification of bicyclic piperidines with enhanced affinity for CatS (IC(50) = 10-30 nM) and sub-micromolar cellular potency (JY Ii IC(50) = 200-720 nM). (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.013
• 作为产物：
  描述：

  甲基2-(苯基氨基)乙酸酯 、 4-乙炔基苯甲醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (S)-2-((4-ethynylbenzyl)amino)-2-phenylacetate
  参考文献：
  名称：

  Pyrazole-based arylalkyne cathepsin S inhibitors. Part II: Optimization of cellular potency

  摘要：

  Basic lipophilic substituents dramatically improved the cellular potency of a previously disclosed series of pyrazole-based arylalkyne cathepsin S inhibitors. The incorporation of substituted benzylamines in the para position of the arylalkyne maintained enzymatic activity (hCatS IC(50) = 80-420 nM) and imparted cellular potency (IC(50) = 0.8-4.0 mu M). Further refinement of the morpholine portion of the pharmacophore enabled the identification of bicyclic piperidines with enhanced affinity for CatS (IC(50) = 10-30 nM) and sub-micromolar cellular potency (JY Ii IC(50) = 200-720 nM). (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.013