2S-(8-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methylamine | 675831-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2S-(8-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methylamine
• 英文别名: [(3S)-5-methoxy-2,3-dihydro-1,4-benzodioxin-3-yl]methanamine
• CAS: 675831-61-5
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: MCQGFLZGUXPQQQ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2S-(8-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methylamine 在 thionyl amide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (3S)-5-methoxy-3-[(sulfamoylamino)methyl]-2,3-dihydro-1,4-benzodioxine
  参考文献：
  名称：

  Novel, Broad-Spectrum Anticonvulsants Containing a Sulfamide Group: Pharmacological Properties of (S)-N-[(6-Chloro-2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]sulfamide (JNJ-26489112)

  摘要：

  Broad-spectrum anticonvulsants are of considerable interest as antiepileptic drugs, especially because of their potential for treating refractory patients. Such "neurostabilizers" have also been used to treat other neurological disorders, including migraine, bipolar disorder, and neuropathic pain. We synthesized a series of sulfamide derivatives (4-9, 10a-i, 11a, 11b, 12) and evaluated their anticonvulsant activity. Thus, we identified promising sulfamide 4 (JNJ-26489112) and explored its pharmacological properties. Compound 4 exhibited excellent anticonvulsant activity in rodents against audiogenic, electrically induced, and chemically induced seizures. Mechanistically, 4 inhibited voltage-gated Na+ channels and N-type Ca2+ channels and was effective as a K+ channel opener. The anticonvulsant profile of 4 suggests that it may be useful for treating multiple forms of epilepsy (generalized tonic-clonic, complex partial, absence seizures), including refractory (or pharmacoresistant) epilepsy, at dose levels that confer a good safety margin. On the basis of its pharmacology and other favorable characteristics, 4 was advanced into human clinical studies.

  DOI：

  10.1021/jm400894u
• 作为产物：
  描述：

  3,4-dimethyl-benzenesulfonic acid (R)-8-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl ester 、 2-azido-8-methoxy-2,3-dihydro-benzo[1,4]dioxine 在 sodium azide 、 水 、 三苯基膦 作用下， 以 DMF (N,N-dimethyl-formamide) 、 四氢呋喃 为溶剂， 反应 72.0h， 以68%的产率得到2S-(8-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methylamine
  参考文献：
  名称：

  [EN] ANTIDEPRESSANT CYCLOALKYLAMINE DERIVATIVES OF 2,3-DIHYDRO-1,4-BENZODIOXAN
  [FR] DERIVES CYCLOALKYLAMINE DE 2,3-DIHYDRO-1,4-BENZODIOXANE ANTIDEPRESSEURS

  摘要：

  公式I的化合物对于治疗抑郁症（包括但不限于重度抑郁障碍、儿童抑郁症和持续性抑郁障碍）、焦虑症、惊恐障碍、创伤后应激障碍、月经前症候群（也称为经前期症候群）、注意力缺陷多动障碍（有或没有多动症）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖症、厌食症和贪食症、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具有有益作用。

  公开号：

  WO2004024723A1

文献信息

• Antidepressant cycloalkylamine derivatives of 2,3-dihydro-1,4-Benzodioxan
  申请人：Evrard Ann Deborah

  公开号：US20060148881A1

  公开（公告）日：2006-07-06

  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.

  I式化合物可用于治疗抑郁症（包括但不限于重度抑郁症、儿童抑郁症和心境不良）、焦虑症、惊恐障碍、创伤后应激障碍、经前期不良情绪障碍（也称经前综合征）、注意力缺陷多动障碍、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、血管运动性潮红、可卡因和酒精成瘾、性功能障碍及相关疾病。
• Antidepressant cycloalkylamine derivatives of 2,3-dihydro-1,4-benzodioxan
  申请人：——

  公开号：US20040127543A1

  公开（公告）日：2004-07-01

  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的化合物对于治疗抑郁症（包括但不限于重度抑郁症、儿童抑郁症和慢性低落情绪）、焦虑、惊恐障碍、创伤后应激障碍、经前期失调症（也称经前综合征）、注意力缺陷障碍（有和没有过度活跃）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖症、进食障碍（如厌食症和贪食症）、血管运动性潮红、可卡因和酒精成瘾、性功能障碍和相关疾病有用。
• ANTIDEPRESSANT CYCLOALKYLAMINE DERIVATES OF 2,3-DIHYDRO-1,4-BENZODIOXAN
  申请人：Wyeth

  公开号：EP1537103A1

  公开（公告）日：2005-06-08
• US7041697B2
  申请人：——

  公开号：US7041697B2

  公开（公告）日：2006-05-09
• US7488751B2
  申请人：——

  公开号：US7488751B2

  公开（公告）日：2009-02-10