4-bromophenyl ((R)-1-(pent-2-ynyl)pyrrolidin-2-yl)methylcarbamate trifluoroacetate | 1378379-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-bromophenyl ((R)-1-(pent-2-ynyl)pyrrolidin-2-yl)methylcarbamate trifluoroacetate
• CAS: 1378379-02-2
• 化学式: C₂HF₃O₂*C₁₇H₂₁BrN₂O₂
• 分子量: 479.294
• InChiKey: WDWNNQNAKXGIOH-XFULWGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.87
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (R)-methyl 1-(pent-2-ynyl)pyrrolidine-2-carboxylate 在 lithium aluminium tetrahydride 、 氨 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 19.0h， 生成 4-bromophenyl ((R)-1-(pent-2-ynyl)pyrrolidin-2-yl)methylcarbamate trifluoroacetate
  参考文献：
  名称：

  Synthesis and Nicotinic Receptor Activity of Chemical Space Analogues of N-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-4-chlorobenzamide (PNU-282,987) and 1,4-Diazabicyclo[3.2.2]nonane-4-carboxylic Acid 4-Bromophenyl Ester (SSR180711)

  摘要：

  The Chemical Universe Generated Databases up to 11 atoms of CNOF (GDB-11) and up to 13 atoms of CNOClS (GDB-13) were used to enumerate analogues of the diamine part of two known alpha 7 nicotinic receptor agonists and construct libraries of virtual analogues of these drugs. The libraries were scored using structure-based (docking to the nicotine binding site of the acetylcholine binding protein 1uw6.pdb) or ligand-based (similarity to the parent drugs) methods, and the top-scoring virtual ligands were inspected for easily accessible synthetic targets. In total, 21 diamines were prepared and acylated with aromatic carboxylic or oxycarbonic acids to produce 85 analogues of the parent drugs. The compounds were profiled by electrophysiology in Xenopus oocytes expressing human nicotinic acetylcholine receptor (nAChR) subtypes alpha 7, alpha 3 beta 2, alpha 4 beta 2, alpha 3 beta 4, or alpha 4 beta 4. Characterization of selected compounds revealed eight inhibitors of the alpha 7 nicotinic receptor and three positive allosteric modulators of the alpha 3 beta 2 nAChR.

  DOI：

  10.1021/jm300030r