trans-3-oxo-3H-spiro[7-aza-2-benzofuran-1,1'-cyclohexane]-4'-carbonitrile | 328233-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: trans-3-oxo-3H-spiro[7-aza-2-benzofuran-1,1'-cyclohexane]-4'-carbonitrile
• CAS: 328233-36-9
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: HFLLUQSIPFAOOZ-GMZHKTEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.98
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-3-oxo-3H-spiro[7-aza-2-benzofuran-1,1'-cyclohexane]-4'-carbonitrile 在 硫酸 、 水 作用下， 以90%的产率得到trans-3-oxo-3H-spiro[7-aza-2-benzofuran-1,1'-cyclohexane]-4'-carboxylic acid
  参考文献：
  名称：

  Discovery of trans-N-[1-(2-fluorophenyl)-3-pyrazolyl]-3-oxospiro[6-azaisobenzofuran-1(3H),1′-cyclohexane]-4′-carboxamide, a potent and orally active neuropeptide Y Y5 receptor antagonist

  摘要：

  A series of trans-3-oxospiro[(aza)isobenzofuran-1(3H),1'-cyclohexane]-4'-carboxamide derivatives were synthesized to identify potent NPY Y5 receptor antagonists. Of the compounds, 21j showed high Y5 binding affinity, metabolic stability and brain and cerebrospinal fluid (CSF) penetration, and low susceptibility to P-glycoprotein transporters. Oral administration of 21j significantly inhibited the Y5 agonist-induced food intake in rats with a minimum effective dose of 1 mg/kg. This compound was selected for proof-of-concept studies in human clinical trials. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.019
• 作为产物：
  描述：

  cis-4'-hydroxy-3H-spiro[7-aza-2-benzofuran-1,1'-cyclohexan]-3-one 、 氰化四乙基铵 以 N,N-二甲基甲酰胺 为溶剂， 生成 trans-3-oxo-3H-spiro[7-aza-2-benzofuran-1,1'-cyclohexane]-4'-carbonitrile
  参考文献：
  名称：

  Identification of positron emission tomography ligands for NPY Y5 receptors in the brain

  摘要：

  A series of trans-3-oxospiro[(aza)isobenzofuran-1(3H),1'-cyclohexane]-4'-carboxamide derivatives were synthesized and profiled for NPY Y5 binding affinity, brain and CSF penetrability in rats, and susceptibility to human and mouse P-glycoprotein transporters in order to develop a PET ligand. Compound 12b exhibited an acceptable profile for a PET ligand, and [C-11]12b was successfully utilized in clinical settings as a Y5 PET ligand. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.103