2,11-dimethoxy-14b-methyl-8,9,14,14b-tetrahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-6(5H)-one

• 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: 2,11-dimethoxy-14b-methyl-8,9,14,14b-tetrahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-6(5H)-one
• 英文别名: 7,19-Dimethoxy-1-methyl-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4(9),5,7,16(21),17,19-heptaen-14-one；7,19-dimethoxy-1-methyl-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4(9),5,7,16(21),17,19-heptaen-14-one
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: QKENDKFCDAGIBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,11-dimethoxy-14b-methyl-8,9,14,14b-tetrahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-6(5H)-one 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到2,11-dimethoxy-14b-methyl-5,6,8,9,14,14b-hexahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinoline
  参考文献：
  名称：

  Gold(I)-Catalyzed Cascade Approach for the Synthesis of Tryptamine-Based Polycyclic Privileged Scaffolds as α₁-Adrenergic Receptor Antagonists

  摘要：

  An efficient and facile gold(I)-catalyzed one-pot cascade protocol has been developed for the synthesis of tryptamine-fused polycyclic privileged structures through the treatment of substituted tryptamines and 2-ethynylbenzoic acids or 2-ethynylphenylacetic acids. This strategy features the formation of one C-C bond and two C-N bonds with high yields and broad substrate tolerance. The selected reduced target molecules are validated to perform as alpha(1)-adrenergic receptors antagonists. The most potent one, 4bh, exhibits an IC50 value of 277 nM on alpha(1A) subtype with a selectivity ratio of 15.8 over alpha(1B) subtype.

  DOI：

  10.1021/jo4017887
• 作为产物：
  描述：

  5-甲氧基色胺 、 2-(2-Ethynyl-4-methoxyphenyl)acetic acid 在 (acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以82%的产率得到2,11-dimethoxy-14b-methyl-8,9,14,14b-tetrahydroindolo[2',3':3,4]pyrido[2,1-a]isoquinolin-6(5H)-one
  参考文献：
  名称：

  Gold(I)-Catalyzed Cascade Approach for the Synthesis of Tryptamine-Based Polycyclic Privileged Scaffolds as α₁-Adrenergic Receptor Antagonists

  摘要：

  An efficient and facile gold(I)-catalyzed one-pot cascade protocol has been developed for the synthesis of tryptamine-fused polycyclic privileged structures through the treatment of substituted tryptamines and 2-ethynylbenzoic acids or 2-ethynylphenylacetic acids. This strategy features the formation of one C-C bond and two C-N bonds with high yields and broad substrate tolerance. The selected reduced target molecules are validated to perform as alpha(1)-adrenergic receptors antagonists. The most potent one, 4bh, exhibits an IC50 value of 277 nM on alpha(1A) subtype with a selectivity ratio of 15.8 over alpha(1B) subtype.

  DOI：

  10.1021/jo4017887