2-(4-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}piperazin-1-yl)quino-line-6-carboxamide | 676131-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}piperazin-1-yl)quino-line-6-carboxamide
• 英文别名: 2-[4-[[(2S)-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-yl]methyl]piperazin-1-yl]quinoline-6-carboxamide
• CAS: 676131-03-6
• 化学式: C₂₇H₂₇N₅O₃
• 分子量: 469.543
• InChiKey: XLBQSSZFTNCULY-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}piperazin-1-yl)quino-line-6-carboxamide 在 盐酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 2-(4-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}piperazin-1-yl)quino-line-6-carboxamide dihydrochloride
  参考文献：
  名称：

  Synthesis, Potency, and in Vivo Evaluation of 2-Piperazin-1-ylquinoline Analogues as Dual Serotonin Reuptake Inhibitors and Serotonin 5-HT_1A Receptor Antagonists

  摘要：

  On the basis of the previously reported clinical candidate, SSA-426 (1), a series of related 2-piperazin-1-ylquinoline derivatives 3-16 were synthesized and evaluated as dual-acting serotonin (5-HT) reuptake inhibitors and 5-HT1A receptor antagonists. In particular, compound 7 exhibits potent functional activities at both the 5-HT transporter and 5-HT1A receptor, good selectivity over the alpha(1)-adrenergic and dopaminergic receptors, acceptable pharmacokinetic properties, and a favorable in vivo profile.

  DOI：

  10.1021/jm900374r
• 作为产物：
  描述：

  2-(piperazin-1-yl) quinoline-6-carboxamide 、 (2R)-quinaldine dioxine brosylate 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以44%的产率得到2-(4-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}piperazin-1-yl)quino-line-6-carboxamide
  参考文献：
  名称：

  Synthesis, Potency, and in Vivo Evaluation of 2-Piperazin-1-ylquinoline Analogues as Dual Serotonin Reuptake Inhibitors and Serotonin 5-HT_1A Receptor Antagonists

  摘要：

  On the basis of the previously reported clinical candidate, SSA-426 (1), a series of related 2-piperazin-1-ylquinoline derivatives 3-16 were synthesized and evaluated as dual-acting serotonin (5-HT) reuptake inhibitors and 5-HT1A receptor antagonists. In particular, compound 7 exhibits potent functional activities at both the 5-HT transporter and 5-HT1A receptor, good selectivity over the alpha(1)-adrenergic and dopaminergic receptors, acceptable pharmacokinetic properties, and a favorable in vivo profile.

  DOI：

  10.1021/jm900374r

文献信息

• Synthesis, Potency, and in Vivo Evaluation of 2-Piperazin-1-ylquinoline Analogues as Dual Serotonin Reuptake Inhibitors and Serotonin 5-HT_1A Receptor Antagonists
  作者：Dahui Zhou、Gary P. Stack、Jennifer Lo、Amedeo A. Failli、Deborah A. Evrard、Boyd L. Harrison、Nicole T. Hatzenbuhler、Megan Tran、Susan Croce、Soo Yi、Jeannette Golembieski、Geoffrey A. Hornby、Margaret Lai、Qian Lin、Lee E. Schechter、Deborah L. Smith、Adam D. Shilling、Christine Huselton、Paul Mitchell、Chad E. Beyer、Terrance H. Andree

  DOI：10.1021/jm900374r

  日期：2009.8.13

  On the basis of the previously reported clinical candidate, SSA-426 (1), a series of related 2-piperazin-1-ylquinoline derivatives 3-16 were synthesized and evaluated as dual-acting serotonin (5-HT) reuptake inhibitors and 5-HT1A receptor antagonists. In particular, compound 7 exhibits potent functional activities at both the 5-HT transporter and 5-HT1A receptor, good selectivity over the alpha(1)-adrenergic and dopaminergic receptors, acceptable pharmacokinetic properties, and a favorable in vivo profile.