tert-butyl 4-(3-(3-(4-chloro-3-iodophenyl)-5-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)-2-hydroxypropyl)piperazine-1-carboxylate | 1198184-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 4-(3-(3-(4-chloro-3-iodophenyl)-5-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)-2-hydroxypropyl)piperazine-1-carboxylate
• CAS: 1198184-16-5
• 化学式: C₂₅H₃₅ClIN₅O₅S
• 分子量: 680.007
• InChiKey: YQRDQESUEPTKQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108.21
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-氯苯乙炔 、 tert-butyl 4-(3-(3-(4-chloro-3-iodophenyl)-5-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)-2-hydroxypropyl)piperazine-1-carboxylate 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 4-(3-{3-[4-chloro-3-(4-chloro-phenylethynyl)-phenyl]-5-methanesulfonyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl}-2-hydroxy-propyl)-piperazine-1-carboxylic acid tert-butyl ester
  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：

  3-(4-chloro-3-iodophenyl)-5-(methylsulfonyl)-1-(oxiran-2-ylmethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine 、 N-Boc-哌嗪 以 乙醇 为溶剂， 生成 tert-butyl 4-(3-(3-(4-chloro-3-iodophenyl)-5-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)-2-hydroxypropyl)piperazine-1-carboxylate
  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