4-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]butan-1-amine | 1365036-35-6

• 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: 4-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]butan-1-amine
• 英文别名: 4-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]butan-1-amine
• CAS: 1365036-35-6
• 化学式: C₁₇H₂₂ClN₃
• 分子量: 303.835
• InChiKey: RJKWXLDNDKXXDU-UHFFFAOYSA-N

物化性质

• 沸点：
  500.9±50.0 °C(Predicted)
• 密度：
  1.207±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  45
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]butan-1-amine 、 3-羟基苯磺酰氯 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 3-hydroxy-N-{4-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]butyl}benzenesulphonamide
  参考文献：
  名称：

  Novel 3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole-Based Multifunctional Ligands with Antipsychotic-Like, Mood-Modulating, and Procognitive Activity

  摘要：

  The most troublesome aspects of behavioral and psychological symptoms of dementia (BPSD) are nowadays addressed by antidepressant, anxiolytic, and antipsychotic drugs, often administered off-label. Considering their modest effectiveness in dementia patients, the increased risk of adverse events and cognitive decline, there is an unmet need for well tolerated and effective therapy of BPSD. We designed and synthesized multifunctional ligands characterized in vitro as high affinity partial agonists of D2R, antagonists of 5-HT6R, and blockers of SERT. Moreover, the molecules activated 5-HT1AR and blocked 5-HT7R while having no relevant affinity for off-target M1R and hERG channel. Compound 16 (N-{244-(5-chloro-1H-iridol-3-y1)-1,2,3,6-tetrahydropyridin-l-yllethy1}-3-methylbenzene-l-sulfonamide), exhibited a broad antipsychotic-, antidepressant-, and anxiolytic-like activity, not eliciting motor impairments in mice. Most importantly, 16 showed memory-enhancing properties and it ameliorated memory deficits induced by scopolamine. The molecule outperformed most important comparators in selected tests, indicating its potential in the treatment of both cognitive and noncognitive (behavioral and psychological) symptoms of dementia.

  DOI：

  10.1021/acs.jmedchem.7b00839
• 作为产物：
  描述：

  4-(5-chloro-3-indolyl)-1,2,3,6-tetrahydropyridine 在 N,N-二异丙基乙胺 、 甲胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 4-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]butan-1-amine
  参考文献：
  名称：

  ARYLOSULFONAMIDES FOR THE TREATMENT OF CNS DISEASES

  摘要：

  化学式（I）的芳基磺胺衍生物及其药用盐。这些化合物可能对中枢神经系统疾病的治疗和/或预防有用。

  公开号：

  US20130172365A1

文献信息

• [EN] ARYLOSULFONAMIDES FOR THE TREATMENT OF CNS DISEASES<br/>[FR] ARYLSULFAMIDES POUR LE TRAITEMENT DE MALADIES DU SNC
  申请人：ADAMED SP ZOO

  公开号：WO2012035123A1

  公开（公告）日：2012-03-22

  Arylsulphonamide derivatives of formula (I) and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of disorders of the central nervous system.

  化学式（I）的芳基磺酰胺衍生物及其药用盐。这些化合物可能对中枢神经系统的治疗和/或预防具有用处。
• US8822517B2
  申请人：——

  公开号：US8822517B2

  公开（公告）日：2014-09-02
• US9120767B2
  申请人：——

  公开号：US9120767B2

  公开（公告）日：2015-09-01