(2S)-8-methyl-2-{[(2S)-2-methyl-4-quinolin-2-ylpiperazin-1-yl]methyl}-2,3-dihydro[1,4]dioxino-[2,3-f]quinoline | 676130-99-7

• 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: (2S)-8-methyl-2-{[(2S)-2-methyl-4-quinolin-2-ylpiperazin-1-yl]methyl}-2,3-dihydro[1,4]dioxino-[2,3-f]quinoline
• 英文别名: (2S)-8-methyl-2-{[(2S)-2-methyl-4-quinolin-2-ylpiperazin-1-yl]methyl}-2,3-dihydro[1,4]dioxino[2,3-f]quinoline；(2S)-8-methyl-2-[[(2S)-2-methyl-4-quinolin-2-ylpiperazin-1-yl]methyl]-2,3-dihydro-[1,4]dioxino[2,3-f]quinoline
• CAS: 676130-99-7
• 化学式: C₂₇H₂₈N₄O₂
• 分子量: 440.545
• InChiKey: SZQOJBUUZPJIPU-FPOVZHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R)-quinaldine dioxine brosylate 、 (S)-2-(3-methylpiperazin-1-yl)quinoline 在 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 silica gel 作用下， 以 二甲基亚砜 、 碳酸氢钠 为溶剂， 反应 16.0h， 以Flash chromatography on silica gel (2/2/96 methanol/2 M ammonia in methanol/methylene chloride) afforded 100 mg (62%) of the title compound as an off-white solid的产率得到(2S)-8-methyl-2-{[(2S)-2-methyl-4-quinolin-2-ylpiperazin-1-yl]methyl}-2,3-dihydro[1,4]dioxino-[2,3-f]quinoline
  参考文献：
  名称：

  Antidepressant arylpiperazine derivatives of heterocycle-fused benzodioxans

  摘要：

  公式I的化合物对于治疗抑郁症（包括但不限于重性抑郁症、儿童抑郁症和心境恶劣）、焦虑症、惊恐障碍、创伤后应激障碍、经前期不良情绪障碍（也称经前综合症）、注意力缺陷障碍（伴有或不伴有多动症）、强迫症、社交焦虑症、广泛性焦虑症、肥胖症、进食障碍（如厌食症和贪食症）、血管运动神经症、可卡因和酒精成瘾、性功能障碍及相关疾病有用。

  公开号：

  US20060276481A1

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 hetrocycle-fused benzodioxans
  申请人：Wyeth

  公开号：US07153849B2

  公开（公告）日：2006-12-26

  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.

  公式为I的化合物对于治疗抑郁症（包括但不限于重度抑郁症、儿童抑郁症和轻度抑郁症）、焦虑症、恐慌症、创伤后应激障碍、经前期不适症（也称经前综合症）、注意力缺陷障碍（伴有或不伴有多动症）、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、性功能障碍以及相关疾病具有治疗作用。
• 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.
• 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