5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide | 1446318-62-2

• 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: 5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide
• CAS: 1446318-62-2
• 化学式: C₁₉H₁₇ClFN₃OS
• 分子量: 389.881
• InChiKey: OBBFAIAGWHKLAH-JXBWDGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54.02
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide 在 叔丁基过氧化氢 、 氨 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以57.6%的产率得到N-[3-[(1S,3S,6S)-5-amino-3-methyl-4-azabicyclo[4.1.0]hept-4-en-3-yl]-4-fluoro-phenyl]-5-chloro-pyridine-2-carboxamide
  参考文献：
  名称：

  BACE1 inhibitors: A head group scan on a series of amides

  摘要：

  A series of amides bearing a variety of amidine head groups was investigated as BACE1 inhibitors with respect to inhibitory activity in a BACE1 enzyme as well as a cell-based assay. Determination of their basicity as well as their properties as substrates of P-glycoprotein revealed that a 2-amino-1,3-oxazine head group would be a suitable starting point for further development of brain penetrating compounds for potential Alzheimer's disease treatment. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.003
• 作为产物：
  描述：

  N-[(1S)-1-(5-bromo-2-fluoro-phenyl)-1-methyl-but-3-enyl]-2-methyl-propane-2-sulfinamide 在 劳森试剂 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 正丁基锂 、 三氟甲磺酸 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 苯甲醚 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 sodium t-butanolate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 68.0h， 生成 5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide
  参考文献：
  名称：

  BACE1 inhibitors: A head group scan on a series of amides

  摘要：

  A series of amides bearing a variety of amidine head groups was investigated as BACE1 inhibitors with respect to inhibitory activity in a BACE1 enzyme as well as a cell-based assay. Determination of their basicity as well as their properties as substrates of P-glycoprotein revealed that a 2-amino-1,3-oxazine head group would be a suitable starting point for further development of brain penetrating compounds for potential Alzheimer's disease treatment. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.003