11-methoxy-7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine | 934490-17-2

• 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: 11-methoxy-7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine
• 英文别名: 17-Methoxy-11-methyl-11,21-diazatetracyclo[12.7.0.03,8.015,20]henicosa-1(14),3,5,7,15(20),16,18-heptaene
• CAS: 934490-17-2
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: AGZPZBJIQLGGOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-methoxy-7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以85%的产率得到11-Methyl-11,21-diazatetracyclo[12.7.0.03,8.015,20]henicosa-1(14),3,5,7,15(20),16,18-heptaen-17-ol
  参考文献：
  名称：

  Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists

  摘要：

  Relying on the high affinities of the benz-indolo-azecine LE 300 (1) and the hydroxylated dibenz-azecine LE 404 (2b) for the D-1/D-5 receptor subtypes, we synthesized methoxylated, hydroxylated and an indole-N methylated derivatives of 1 (Fig. 1). Hydroxylation of azecine derivatives is beneficial with regard to the affinities and selectivities for all the dopamine receptor subtypes. The 'serotonin-derived' 3-oxygenated target compounds but not the 11-oxygenated analogues were superior to the unsubstituted LE 300. 11-Methoxy-7,14-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f[3]bcnzazecine (3e) was found to be the most potent antagonist at D-2/D-3/D-4 and D-5 receptor subtypes (K-i for D-5=0.23 nmol) of all known benz-indolo-azecines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.093
• 作为产物：
  描述：

  5-甲氧基色胺 在 氨 、 sodium 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 5.0h， 生成 11-methoxy-7-methyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine
  参考文献：
  名称：

  Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists

  摘要：

  Relying on the high affinities of the benz-indolo-azecine LE 300 (1) and the hydroxylated dibenz-azecine LE 404 (2b) for the D-1/D-5 receptor subtypes, we synthesized methoxylated, hydroxylated and an indole-N methylated derivatives of 1 (Fig. 1). Hydroxylation of azecine derivatives is beneficial with regard to the affinities and selectivities for all the dopamine receptor subtypes. The 'serotonin-derived' 3-oxygenated target compounds but not the 11-oxygenated analogues were superior to the unsubstituted LE 300. 11-Methoxy-7,14-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f[3]bcnzazecine (3e) was found to be the most potent antagonist at D-2/D-3/D-4 and D-5 receptor subtypes (K-i for D-5=0.23 nmol) of all known benz-indolo-azecines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.093

文献信息

• Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists
  作者：Christoph Enzensperger、Susann Kilian、Marit Ackermann、Anne Koch、Kristin Kelch、Jochen Lehmann

  DOI：10.1016/j.bmcl.2006.11.093

  日期：2007.3

  Relying on the high affinities of the benz-indolo-azecine LE 300 (1) and the hydroxylated dibenz-azecine LE 404 (2b) for the D-1/D-5 receptor subtypes, we synthesized methoxylated, hydroxylated and an indole-N methylated derivatives of 1 (Fig. 1). Hydroxylation of azecine derivatives is beneficial with regard to the affinities and selectivities for all the dopamine receptor subtypes. The 'serotonin-derived' 3-oxygenated target compounds but not the 11-oxygenated analogues were superior to the unsubstituted LE 300. 11-Methoxy-7,14-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f[3]bcnzazecine (3e) was found to be the most potent antagonist at D-2/D-3/D-4 and D-5 receptor subtypes (K-i for D-5=0.23 nmol) of all known benz-indolo-azecines. (c) 2006 Elsevier Ltd. All rights reserved.