1-[2-(2-pentyl-4,5,6,7-tetrahydrobenzothiophen-5-yl)acetyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine ethylene ketal | 945953-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 1-[2-(2-pentyl-4,5,6,7-tetrahydrobenzothiophen-5-yl)acetyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine ethylene ketal
• 英文别名: 1-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-2-(2'-pentylspiro[1,3-dioxolane-2,4'-6,7-dihydro-5H-1-benzothiophene]-5'-yl)ethanone
• CAS: 945953-52-6
• 化学式: C₂₉H₃₅FN₂O₄S
• 分子量: 526.672
• InChiKey: ZBUROXMZGMESFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  93
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2-(2-pentyl-4,5,6,7-tetrahydrobenzothiophen-5-yl)acetyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine ethylene ketal 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以0.30 g的产率得到5-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-2-pentyl-6,7-dihydro-5H-1-benzothiophen-4-one
  参考文献：
  名称：

  Multistructure 3D-QSAR Studies on a Series of Conformationally Constrained Butyrophenones Docked into a New Homology Model of the 5-HT_2A Receptor

  摘要：

  The present study is part of a long-term research project aiming to gain insight into the mechanism of action of atypical antipsychotics. Here we describe a 3D-QSAR study carried out on a series of butyrophenones with affinity for the serotonin-2A receptor, aligned by docking into the binding site of a receptor model. The series studied has two peculiarities: (i) all the compounds have a chiral center and can be represented by two enantiomeric structures, and (ii) many of the structures can bind the receptor in two alternative orientations, posing the problem of how to select a single representative structure for every compound. We have used an original solution consisting of the simultaneous use of multiple structures, representing different configurations, binding conformations, and positions. The final model showed good statistical quality (n = 426, r(2) = 0.84, q(LOO)(2) = 0.81) and its interpretation provided useful information, not obtainable from the simple inspection of the ligand-receptor complexes.

  DOI：

  10.1021/jm070277a
• 作为产物：
  描述：

  6-氟-3-(哌啶-4-基)苯并[D]异恶唑 在 1-羟基苯并三唑 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 121.0h， 生成 1-[2-(2-pentyl-4,5,6,7-tetrahydrobenzothiophen-5-yl)acetyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine ethylene ketal
  参考文献：
  名称：

  Multistructure 3D-QSAR Studies on a Series of Conformationally Constrained Butyrophenones Docked into a New Homology Model of the 5-HT_2A Receptor

  摘要：

  The present study is part of a long-term research project aiming to gain insight into the mechanism of action of atypical antipsychotics. Here we describe a 3D-QSAR study carried out on a series of butyrophenones with affinity for the serotonin-2A receptor, aligned by docking into the binding site of a receptor model. The series studied has two peculiarities: (i) all the compounds have a chiral center and can be represented by two enantiomeric structures, and (ii) many of the structures can bind the receptor in two alternative orientations, posing the problem of how to select a single representative structure for every compound. We have used an original solution consisting of the simultaneous use of multiple structures, representing different configurations, binding conformations, and positions. The final model showed good statistical quality (n = 426, r(2) = 0.84, q(LOO)(2) = 0.81) and its interpretation provided useful information, not obtainable from the simple inspection of the ligand-receptor complexes.

  DOI：

  10.1021/jm070277a