2-(2,2-Dimethylpropyl)-6,6-dimethyl-5,7-dihydropyrazolo[1,5-a]pyridin-4-one | 1414357-06-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,2-Dimethylpropyl)-6,6-dimethyl-5,7-dihydropyrazolo[1,5-a]pyridin-4-one
• 英文别名: 2-(2,2-dimethylpropyl)-6,6-dimethyl-5,7-dihydropyrazolo[1,5-a]pyridin-4-one
• CAS: 1414357-06-4
• 化学式: C₁₄H₂₂N₂O
• 分子量: 234.341
• InChiKey: URHYNFBYZASZEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,2-Dimethylpropyl)-6,6-dimethyl-5,7-dihydropyrazolo[1,5-a]pyridin-4-one 在 titanium(IV) tetraethanolate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-N-[(4S)-2-(2,2-dimethylpropyl)-6,6-dimethyl-5,7-dihydro-4H-pyrazolo[1,5-a]pyridin-4-yl]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Design and synthesis of potent hydroxyethylamine (HEA) BACE-1 inhibitors carrying prime side 4,5,6,7-tetrahydrobenzazole and 4,5,6,7-tetrahydropyridinoazole templates

  摘要：

  A set of low molecular weight compounds containing a hydroxyethylamine (HEA) core structure with different prime side alkyl substituted 4,5,6,7-tetrahydrobenzazoles and one 4,5,6,7-tetrahydropyridinoazole was synthesized. Striking differences were observed on potencies in the BACE-1 enzymatic and cellular assays depending on the nature of the heteroatoms in the bicyclic ring, from the low active compound 4 to inhibitor 6, displaying BACE-1 IC50 values of 44 nM (enzyme assay) and 65 nM (cell-based assay). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.097
• 作为产物：
  描述：

  3,3-二甲基丁醛 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 叔丁基锂 、 potassium hydride 、 一水合肼 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 、 正戊烷 为溶剂， -75.0~160.0 ℃ 、101.33 kPa 条件下， 生成 2-(2,2-Dimethylpropyl)-6,6-dimethyl-5,7-dihydropyrazolo[1,5-a]pyridin-4-one
  参考文献：
  名称：

  Design and synthesis of potent hydroxyethylamine (HEA) BACE-1 inhibitors carrying prime side 4,5,6,7-tetrahydrobenzazole and 4,5,6,7-tetrahydropyridinoazole templates

  摘要：

  A set of low molecular weight compounds containing a hydroxyethylamine (HEA) core structure with different prime side alkyl substituted 4,5,6,7-tetrahydrobenzazoles and one 4,5,6,7-tetrahydropyridinoazole was synthesized. Striking differences were observed on potencies in the BACE-1 enzymatic and cellular assays depending on the nature of the heteroatoms in the bicyclic ring, from the low active compound 4 to inhibitor 6, displaying BACE-1 IC50 values of 44 nM (enzyme assay) and 65 nM (cell-based assay). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.097