2-fluoro-10-methoxy-13b-methyl-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-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-fluoro-10-methoxy-13b-methyl-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
• 英文别名: 5-Fluoro-16-methoxy-2-methyl-10,20-diazapentacyclo[11.7.0.02,10.03,8.014,19]icosa-1(13),3(8),4,6,14(19),15,17-heptaen-9-one；5-fluoro-16-methoxy-2-methyl-10,20-diazapentacyclo[11.7.0.02,10.03,8.014,19]icosa-1(13),3(8),4,6,14(19),15,17-heptaen-9-one
• 化学式: C₂₀H₁₇FN₂O₂
• 分子量: 336.366
• InChiKey: SMROVGVAZQEZFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-甲氧基色胺 、 2-Ethynyl-4-fluorobenzoic 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87%的产率得到2-fluoro-10-methoxy-13b-methyl-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-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

文献信息

• Gold(I)-Catalyzed Cascade Approach for the Synthesis of Tryptamine-Based Polycyclic Privileged Scaffolds as α₁-Adrenergic Receptor Antagonists
  作者：Zeng Li、Jing Li、Nan Yang、Ying Chen、Yu Zhou、Xun Ji、Lei Zhang、Jinfang Wang、Xin Xie、Hong Liu

  DOI：10.1021/jo4017887

  日期：2013.11.1

  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.