7,8-dimethyl-5,6,8,9,14,14b-hexahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-7-ium iodide | 1336919-37-9

• 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: 7,8-dimethyl-5,6,8,9,14,14b-hexahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-7-ium iodide
• 英文别名: 12,13-Dimethyl-3-aza-13-azoniapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16,18,20-heptaene;iodide
• CAS: 1336919-37-9
• 化学式: C₂₁H₂₃N₂*I
• 分子量: 430.332
• InChiKey: NFACZVRYALHOIO-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：
  0
• 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：

  7,8-dimethyl-5,6,8,9,14,14b-hexahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-7-ium iodide 在 氨 、 sodium 作用下， 反应 0.17h， 以89%的产率得到(8RS)-7,8-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine
  参考文献：
  名称：

  Chiral Indolo[3,2-f][3]benzazecine-Type Dopamine Receptor Antagonists: Synthesis and Activity of Racemic and Enantiopure Derivatives

  摘要：

  Racemic and enantiopure 8-substituted derivatives of the lead dopamine receptor antagonist LE 300 (1) were prepared, and their affinities for the dopamine receptors (D(1)-D(5)) were tested. The separate enantiomers showed significantly different affinities; the (8S)-methyl and (8R)-hyroxymethyl derivatives where the substituents point below the reference plane of the indolo[3,2-f][3]benzazecine scaffold were markedly more active than their enantiomeric counterparts. The racemic 8-carboxy derivative was shown to be selective for the D(5)-receptor, even against D(1).

  DOI：

  10.1021/jm200676f
• 作为产物：
  描述：

  3-(2-nitroprop-1-en-1-yl)-1H-indole 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 反应 36.0h， 生成 7,8-dimethyl-5,6,8,9,14,14b-hexahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-7-ium iodide
  参考文献：
  名称：

  Chiral Indolo[3,2-f][3]benzazecine-Type Dopamine Receptor Antagonists: Synthesis and Activity of Racemic and Enantiopure Derivatives

  摘要：

  Racemic and enantiopure 8-substituted derivatives of the lead dopamine receptor antagonist LE 300 (1) were prepared, and their affinities for the dopamine receptors (D(1)-D(5)) were tested. The separate enantiomers showed significantly different affinities; the (8S)-methyl and (8R)-hyroxymethyl derivatives where the substituents point below the reference plane of the indolo[3,2-f][3]benzazecine scaffold were markedly more active than their enantiomeric counterparts. The racemic 8-carboxy derivative was shown to be selective for the D(5)-receptor, even against D(1).

  DOI：

  10.1021/jm200676f

文献信息

• Chiral Indolo[3,2-<i>f</i>][3]benzazecine-Type Dopamine Receptor Antagonists: Synthesis and Activity of Racemic and Enantiopure Derivatives
  作者：Dina Robaa、Christoph Enzensperger、Shams ElDin AbulAzm、Mohamed M. Hefnawy、Hussein I. El-Subbagh、Tanveer A. Wani、Jochen Lehmann

  DOI：10.1021/jm200676f

  日期：2011.10.27

  Racemic and enantiopure 8-substituted derivatives of the lead dopamine receptor antagonist LE 300 (1) were prepared, and their affinities for the dopamine receptors (D(1)-D(5)) were tested. The separate enantiomers showed significantly different affinities; the (8S)-methyl and (8R)-hyroxymethyl derivatives where the substituents point below the reference plane of the indolo[3,2-f][3]benzazecine scaffold were markedly more active than their enantiomeric counterparts. The racemic 8-carboxy derivative was shown to be selective for the D(5)-receptor, even against D(1).