methyl (8R)-5,6,8,9,14,14b-hexahydroindolo-[2',3':3,4]pyrido[2,1-a]isoquinoline-8-carboxylate | 1336919-47-1

• 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: methyl (8R)-5,6,8,9,14,14b-hexahydroindolo-[2',3':3,4]pyrido[2,1-a]isoquinoline-8-carboxylate
• 英文别名: methyl (12R)-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16,18,20-heptaene-12-carboxylate
• CAS: 1336919-47-1
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: BNDMJYQQUXOWNH-QSVWIEALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (8R)-5,6,8,9,14,14b-hexahydroindolo-[2',3':3,4]pyrido[2,1-a]isoquinoline-8-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82.6%的产率得到[(8R)-5,6,8,9,14,14b-hexahydroindolo-[2',3':3,4]pyrido[2,1-a]isoquinolin-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