2,3,5,6,11,11b-Hexahydro-3-oxo-11b-phenyl-1H-indolizino<8,7-b>indole | 741-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3,5,6,11,11b-Hexahydro-3-oxo-11b-phenyl-1H-indolizino<8,7-b>indole
• 英文别名: 11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one；11b-phenyl-1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-one；11b-phenyl-1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-one；3-Oxo-11b-phenyl-1.2.3.5.6.11b-hexahydro-11H-pyrrolo<2.1-a>-β-carbolin；11b-phenyl-2,5,6,11-tetrahydro-1H-indolizino[8,7-b]indol-3-one
• CAS: 741-25-3
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: OQHYPBCEAGZUGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  263-264 °C
• 沸点：
  532.0±49.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,5,6,11,11b-Hexahydro-3-oxo-11b-phenyl-1H-indolizino<8,7-b>indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 11b-phenyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist

  摘要：

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.

  DOI：

  10.1021/jm050846j
• 作为产物：
  描述：

  N-[2-(1H-indol-3-yl)ethyl]-4-oxo-4-phenylbutanamide 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 2,3,5,6,11,11b-Hexahydro-3-oxo-11b-phenyl-1H-indolizino<8,7-b>indole
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist

  摘要：

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.

  DOI：

  10.1021/jm050846j

文献信息

• Racemic and diastereoselective construction of indole alkaloids under solvent- and catalyst-free microwave-assisted Pictet–Spengler condensation
  作者：Mouhamad Jida、Olivier-Mohamad Soueidan、Benoit Deprez、Guillaume Laconde、Rebecca Deprez-Poulain

  DOI：10.1039/c2gc16596a

  日期：——

  An environment-friendly high-yielding method for the racemic and asymmetric diastereoselective preparation of indole alkaloids via Pictet–Spengler reaction is reported. The reaction proceeds with short reaction times under solvent-free and microwave-irradiation conditions.

  报道了一种环境友好且高产率的吲哚生物碱制备方法，通过Pictet-Spengler反应实现外消旋和不对称对映选择性合成。该反应在无溶剂和微波辐射条件下进行，反应时间短。
• Carboxyl-mediated Pictet-Spengler reaction. Improved synthesis of 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino[8,7-b]indoles from tryptamine-2-carboxylic acids
  作者：Krishnaswamy Narayanan、James M. Cook

  DOI：10.1021/jo00019a056

  日期：1991.9