3-bromo-5-(3-methoxyphenoxy)pyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-5-(3-methoxyphenoxy)pyridine
• 化学式: C₁₂H₁₀BrNO₂
• 分子量: 280.121
• InChiKey: MQKKCRQPKWYAQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-(3-methoxyphenoxy)pyridine 、 tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 1.15h， 生成 7-(5-(3-methoxyphenoxy)pyridin-3-yl)-3-azabicyclo[3.3.1]non-7-ene trifluoroacetate
  参考文献：
  名称：

  Structure–Activity Studies of 7-Heteroaryl-3-azabicyclo[3.3.1]non-6-enes: A Novel Class of Highly Potent Nicotinic Receptor Ligands

  摘要：

  The potential for nicotinic ligands with affinity for the alpha 4 beta 2 or alpha 7 subtypes to treat such diverse diseases as nicotine addiction, neuropathic pain, and neurodegenerative and cognitive disorders has been exhibited clinically for several compounds while preclinical activity in relevant in vivo models has been demonstrated for many more. For several therapeutic programs, we sought nicotinic ligands with various combinations of affinity and function across both subtypes, with an emphasis on dual alpha 4 beta 2-alpha 7 ligands, to explore, the possibility of synergistic effects. We report here the structure-activity relationships (SAR) for a novel series of 7-heteroaryl-3-azabicyclo[3.3.1]non-6-enes and characterize many of the analogues for activity at multiple nicotinic subtypes.

  DOI：

  10.1021/jm3011299
• 作为产物：
  描述：

  3,5-二溴吡啶 在 氢化钾 、 铜 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 、 mineral oil 为溶剂， 反应 65.0h， 生成 3-bromo-5-(3-methoxyphenoxy)pyridine
  参考文献：
  名称：

  Structure–Activity Studies of 7-Heteroaryl-3-azabicyclo[3.3.1]non-6-enes: A Novel Class of Highly Potent Nicotinic Receptor Ligands

  摘要：

  The potential for nicotinic ligands with affinity for the alpha 4 beta 2 or alpha 7 subtypes to treat such diverse diseases as nicotine addiction, neuropathic pain, and neurodegenerative and cognitive disorders has been exhibited clinically for several compounds while preclinical activity in relevant in vivo models has been demonstrated for many more. For several therapeutic programs, we sought nicotinic ligands with various combinations of affinity and function across both subtypes, with an emphasis on dual alpha 4 beta 2-alpha 7 ligands, to explore, the possibility of synergistic effects. We report here the structure-activity relationships (SAR) for a novel series of 7-heteroaryl-3-azabicyclo[3.3.1]non-6-enes and characterize many of the analogues for activity at multiple nicotinic subtypes.

  DOI：

  10.1021/jm3011299

文献信息

• MTA-Cooperative PRMT5 Inhibitors
  申请人：Mirati Therapeutics, Inc.

  公开号：US20210078994A1

  公开（公告）日：2021-03-18

  The present invention relates to compounds that inhibit Protein Arginine N-Methyl Transferase 5 (PRMT5) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.

  本发明涉及抑制蛋白精氨酸N-甲基转移酶5（PRMT5）活性的化合物。具体而言，本发明涉及化合物、药物组合物和使用方法，例如使用本发明的化合物和药物组合物治疗癌症的方法。
• Pharmaceutical compositions and methods for use
  申请人：——

  公开号：US20020013309A1

  公开（公告）日：2002-01-31

  The present invention relates to diazabicyclic compounds, preferably to N-aryl diazabicyclic compounds. Of particular interest are 2-pyridyl diazabicyclic compounds, such as (1S,4S)-2-(5-(3-methoxyphenoxy)-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane. Other exemplary compounds of the present invention include: (1S,4S)-2-(5-(4-methoxyphenoxy)-3-pyridyl)-2,5-diazabicyclo[2.2.1 ]heptane, (1S,4S)-2-(5-(3,4-dimethoxyphenoxy)-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane, (1S,4S)-2-(5-(4-fluorophenoxy)-3-pyridyl)-2,5-diazabicyclo[2.2.1 ]heptane, and (1S,4S)-2-(5-benzoyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane. The present invention also relates to prodrug derivatives of the compounds of the present invention.

  本发明涉及二氮杂双环化合物，优选为N-芳基二氮杂双环化合物。特别感兴趣的是2-吡啶基二氮杂双环化合物，例如(1S,4S)-2-(5-(3-甲氧基苯氧基)-3-吡啶基)-2,5-二氮杂双环[2.2.1]庚烷。本发明的其他示例化合物包括：(1S,4S)-2-(5-(4-甲氧基苯氧基)-3-吡啶基)-2,5-二氮杂双环[2.2.1]庚烷，(1S,4S)-2-(5-(3,4-二甲氧基苯氧基)-3-吡啶基)-2,5-二氮杂双环[2.2.1]庚烷，(1S,4S)-2-(5-(4-氟苯氧基)-3-吡啶基)-2,5-二氮杂双环[2.2.1]庚烷和(1S,4S)-2-(5-苯甲酰基-3-吡啶基)-2,5-二氮杂双环[2.2.1]庚烷。本发明还涉及本发明化合物的前药衍生物。
• MTA-cooperative PRMT5 inhibitors
  申请人：Mirati Therapeutics, Inc.

  公开号：US11479551B2

  公开（公告）日：2022-10-25

  The present invention relates to compounds that inhibit Protein Arginine N-Methyl Transferase 5 (PRMT5) activity. In particular, the present invention relates to compounds of Formula (I) to pharmaceutical compositions comprising compounds of Formula (I) and to methods of use thereof, such as methods of treating cancer using the compounds of Formula (I) and pharmaceutical compositions comprising those compounds.

  本发明涉及抑制蛋白精氨酸 N-甲基转移酶 5（PRMT5）活性的化合物。特别是，本发明涉及式 (I) 的化合物 涉及包含式（I）化合物的药物组合物及其使用方法，例如使用式（I）化合物和包含这些化合物的药物组合物治疗癌症的方法。
• USRE041439E1
  申请人：——

  公开号：——

  公开（公告）日：——
• HETEROARYLDIAZABICYCLOALKANES AS NICOTINIC CHOLINERGIC RECEPTOR LIGANDS
  申请人：Targacept, Inc.

  公开号：EP1289996A1

  公开（公告）日：2003-03-12