4-methyl-11b-phenyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indolium iodide

• 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: 4-methyl-11b-phenyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indolium iodide
• 英文别名: 2,3,5,6,11,11b-hexahydro-4-methyl-11b-phenyl-1H-indolizino[8,7-b]indolium iodide；4-methyl-11b-phenyl-1,2,3,5,6,11-hexahydroindolizino[8,7-b]indol-4-ium;iodide
• 化学式: C₂₁H₂₃N₂*I
• 分子量: 430.332
• InChiKey: DJVFGQWSWXEFRZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-11b-phenyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indolium iodide 在 氨 、 lithium 作用下， 生成 3-methyl-7-phenyl-1,2,3,4,5,6,7,8-octahydro-azonino[5,4-b]indole
  参考文献：
  名称：

  Indole fused heterocyclic diuretic compounds

  摘要：

  通过在液氨中使用锂对应的季铵碘化物盐进行裂解，制备了取代的1,2,4,5,6,7,8,9-八氢-3H-氮杂环[5,4-b]-吲哚和取代的1,2,3,4,5,6,7,8-八氢-氮杂环[5,4-b]-吲哚。这些产物具有利尿活性。

  公开号：

  US03943148A1
• 作为产物：
  描述：

  3-苯丙烯溴酸酯 在 盐酸 、 lithium aluminium tetrahydride 、 三甲胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 为溶剂， 生成 4-methyl-11b-phenyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indolium iodide
  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

• Indole fused heterocyclic diuretic compounds
  申请人：American Home Products Corporation

  公开号：US03943148A1

  公开（公告）日：1976-03-09

  Substituted 1,2,4,5,6,7,8,9-octahydro-3H-azecino[5,4-b]-indoles and substituted 1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]-indoles are prepared by cleavage of the corresponding quaternary alkyl iodide salts with lithium in liquid ammonia. The products possess diuretic activity.

  通过在液氨中使用锂对应的季铵碘化物盐进行裂解，制备了取代的1,2,4,5,6,7,8,9-八氢-3H-氮杂环[5,4-b]-吲哚和取代的1,2,3,4,5,6,7,8-八氢-氮杂环[5,4-b]-吲哚。这些产物具有利尿活性。
• US3943148A
  申请人：——

  公开号：US3943148A

  公开（公告）日：1976-03-09
• 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
  作者：Barbara Hoefgen、Michael Decker、Patrick Mohr、Astrid M. Schramm、Sherif A. F. Rostom、Hussein El-Subbagh、Peter M. Schweikert、Dirk R. Rudolf、Matthias U. Kassack、Jochen Lehmann

  DOI：10.1021/jm050846j

  日期：2006.1.1

  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.