7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine-8-carboxylic acid | 1336919-56-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine-8-carboxylic acid
• 英文别名: 11-Methyl-11,21-diazatetracyclo[12.7.0.03,8.015,20]henicosa-1(14),3,5,7,15,17,19-heptaene-12-carboxylic acid
• CAS: 1336919-56-2
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: NUVPQYAINAPNNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine-8-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以42%的产率得到[(8RS)-7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine-8-yl]methanol
  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：

  8-carboxy-7-methyl-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67%的产率得到7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine-8-carboxylic acid
  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