(S)-2-(allyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanamine | 1385068-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(allyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanamine
• CAS: 1385068-39-2
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: BCCHYIXMUMKQLC-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  53.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(allyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanamine 在 Hoveyda-Grubbs catalyst second generation 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 21.92h， 生成 N-[(S)-4-((S)-1,2-dihydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1(18),14,16-trien-16-yl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  Highly potent macrocyclic BACE-1 inhibitors incorporating a hydroxyethylamine core: Design, synthesis and X-ray crystal structures of enzyme inhibitor complexes

  摘要：

  A series of P1-P3 linked macrocyclic BACE-1 inhibitors containing a hydroxyethylamine (HEA) isostere scaffold has been synthesized. All inhibitors comprise a toluene or N-phenylmethanesulfonamide P2 moiety. Excellent BACE-1 potencies, both in enzymatic and cell-based assays, were observed in this series of target compounds, with the best candidates displaying cell-based IC50 values in the low nanomolar range. As an attempt to improve potency, a phenyl substituent aiming at the S3 subpocket was introduced in the macrocyclic ring. X-ray analyzes were performed on selected compounds, and enzyme-inhibitor interactions are discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.039
• 作为产物：
  描述：

  (2S,3S)-3-azido-1,2-O-isopropylidene-1,2,4-butanetriol 在 1,3-丙二硫醇 、 三乙胺 、 silver(l) oxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.0h， 生成 (S)-2-(allyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanamine
  参考文献：
  名称：

  Highly potent macrocyclic BACE-1 inhibitors incorporating a hydroxyethylamine core: Design, synthesis and X-ray crystal structures of enzyme inhibitor complexes

  摘要：

  A series of P1-P3 linked macrocyclic BACE-1 inhibitors containing a hydroxyethylamine (HEA) isostere scaffold has been synthesized. All inhibitors comprise a toluene or N-phenylmethanesulfonamide P2 moiety. Excellent BACE-1 potencies, both in enzymatic and cell-based assays, were observed in this series of target compounds, with the best candidates displaying cell-based IC50 values in the low nanomolar range. As an attempt to improve potency, a phenyl substituent aiming at the S3 subpocket was introduced in the macrocyclic ring. X-ray analyzes were performed on selected compounds, and enzyme-inhibitor interactions are discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.039