2-(4-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}piperazin-1-yl)-quinoline-6-carbonitrile | 676130-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 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)-quinoline-6-carbonitrile
• 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-carbonitrile
• CAS: 676130-94-2
• 化学式: C₂₇H₂₅N₅O₂
• 分子量: 451.528
• InChiKey: AIBSVCNXTNBLRF-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.5
• 氢给体数：
  0
• 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)-quinoline-6-carbonitrile 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)-quinoline-6-carbonitrile 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：

  (2R)-quinaldine dioxine brosylate 、 2-(piperazin-1-yl)quinoline-6-carbonitrile 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以72%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)-quinoline-6-carbonitrile
  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

• [EN] ANTIDEPRESSANT ARYLPIPERAZINE DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXANS<br/>[FR] DERIVES ARYLPIPERAZINES ANTIDEPRESSEURS DE BENZODIOXANES A FUSION HETEROCYCLIQUE
  申请人：WYETH CORP

  公开号：WO2004024731A1

  公开（公告）日：2004-03-25

  Compounds of the formula I: are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as pre-menstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive-compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.

  公式I的化合物对治疗抑郁症（包括但不限于重性抑郁障碍、儿童抑郁症和心境恶劣障碍）、焦虑症、恐慌障碍、创伤后应激障碍、经前期情感障碍（也称为经前综合征）、注意力缺陷障碍（伴有和不伴有多动症）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖、厌食症和暴食症等进食障碍、血管运动性潮红、可卡因和酒精成瘾、性功能障碍及相关疾病方面具有用处。
• Antidepressant arylpiperazine derivatives of heterocycle-fused benzodioxans
  申请人：——

  公开号：US20040142926A1

  公开（公告）日：2004-07-22

  Compounds of the formula I: 1 are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as pre-menstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive-compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity, eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.

  公式I:1的化合物可用于治疗抑郁症（包括但不限于重度抑郁障碍、儿童抑郁症和慢性抑郁症）、焦虑症、恐慌症、创伤后应激障碍、月经前失调症（也称为经前综合症）、注意力缺陷多动障碍（有或没有多动症）、强迫症、社交焦虑症、广泛性焦虑症、肥胖症、饮食失调如厌食症和贪食症、潮红、可卡因和酒精成瘾、性功能障碍及相关疾病的治疗。
• ANTIDEPRESSANT ARYLPIPERAZINE DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXANS
  申请人：Wyeth

  公开号：EP1537121A1

  公开（公告）日：2005-06-08
• US7153849B2
  申请人：——

  公开号：US7153849B2

  公开（公告）日：2006-12-26