2-(2-chloro-ethyl)-N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-benzamide | 934490-22-9

• 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-(2-chloro-ethyl)-N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-benzamide
• CAS: 934490-22-9
• 化学式: C₂₀H₂₁ClN₂O₂
• 分子量: 356.852
• InChiKey: QAKXHBOQOYDDDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-ethyl)-N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-benzamide 在 三氯氧磷 、 sodium tetrahydroborate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 5.0h， 以50%的产率得到10-methoxy-5,6a,7,8,13,13b-hexahydro-6H-13-aza-indeno[1,2-c]phenanthrene
  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 、 2-(2-chloroethyl)benzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到2-(2-chloro-ethyl)-N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-benzamide
  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