3-溴-5-(4-氯苯氧基)吡啶 | 28232-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-溴-5-(4-氯苯氧基)吡啶
• 英文名称: 3-bromo-5-(4-chlorophenoxy)pyridine
• CAS: 28232-66-8
• 化学式: C₁₁H₇BrClNO
• 分子量: 284.54
• InChiKey: WBVDIRRTMMAHKU-UHFFFAOYSA-N

物化性质

• 熔点：
  79 ºC
• 沸点：
  341.4±32.0 °C(Predicted)
• 密度：
  1.568

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-溴-5-(4-氯苯氧基)吡啶 、 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-(4-chlorophenoxy)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-溴-5-(4-氯苯氧基)吡啶
  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

• 一种含2-羟基苯甲酸的三环类XOR/URAT1双重抑制剂及其制备方法与应用
  申请人：华南理工大学

  公开号：CN114805192B

  公开（公告）日：2023-05-23

  本发明公开了一种含2‑羟基苯甲酸的三环类XOR/URAT1双重抑制剂及其制备方法与应用，属于XOR/URAT1双重抑制剂领域。该含2‑羟基苯甲酸的三环类XOR/URAT1双重抑制剂的结构如式(A)所示：其中，X为O或NH，R1为氢、烷基、烷氧基、卤素或氰基，R2为氢、烷基、烷氧基、卤素或氰基。本发明的含2‑羟基苯甲酸的三环类XOR/URAT1双重抑制剂与已知XOR/URAT1双重抑制剂有不同的化学结构；其对与痛风有关的XOR和URAT1这两个关键作用靶点都表现出优良的抑制作用，可应用于制备抗高尿酸血症或痛风药物。
• Design, synthesis, and biological evaluation of 3-phenyl substituted pyridine derivatives as potential dual inhibitors of XOR and URAT1
  作者：Chao Yang、Haojie Cai、Xinying Zhu、Lei Zhang、Jing Li

  DOI：10.1016/j.ejmech.2024.116407

  日期：2024.5

  agents might not achieve aim of lowering uric acid to ideal value in clinic. Thus, therapeutic strategies of combining XOR inhibitors with uricosuric drugs were proposed and implemented. Based on our initial work of virtual screening, and were potential hits for dual-targeted inhibitors on XOR/URAT1. By docking / with XOR/URAT1 respectively, compounds were designed to get different degree of inhibition

  黄嘌呤氧化还原酶 (XOR) 和尿酸转运蛋白 1 (URAT1) 分别是涉及尿酸产生和重吸收的两个最广泛研究的靶标。已上市的药物几乎都以XOR或URAT1为靶点，但有时单一药物可能无法达到临床降低尿酸至理想值的目的。因此，提出并实施了XOR抑制剂与促尿酸排泄药物联合的治疗策略。基于我们最初的虚拟筛选工作，XOR/URAT1 的双靶点抑制剂具有潜在的潜力。通过分别与XOR/URAT1对接，设计化合物对XOR和URAT1产生不同程度的抑制效果，其中对XOR（IC = 0.037 ± 0.001 μM）和URAT1（IC = 546.70 ± 32.60 μM）显示出最佳的抑制效果。 。与XOR/URAT1的进一步对接研究导致设计了对XOR和URAT1抑制活性显着提高的化合物，例如和。特别是，XOR 的 IC 值为 0.006 ± 0.000 μM，优于非布索坦 (IC = 0.008 ± 0.000
• Synthesis of novel halo-oxybispyridines, new building blocks in cholinergic medicinal chemistry
  作者：Anne Sophie Voisin、Alexandre Bouillon、Jean-Charles Lancelot、Aurélien Lesnard、Sylvain Rault

  DOI：10.1016/j.tet.2006.04.002

  日期：2006.6

  This paper describes a method for the preparation of oxybispyridines bearing several halogens, which could be further transformed into other functional groups thus giving access to libraries with the bis-pyridyl ether moiety as the common structural feature of interest in cholinergic medicinal chemistry. Scope and limitation of the method are outlined. (c) 2006 Elsevier Ltd. All rights reserved.
• Structure–Activity Studies of 7-Heteroaryl-3-azabicyclo[3.3.1]non-6-enes: A Novel Class of Highly Potent Nicotinic Receptor Ligands
  作者：Scott R. Breining、Matt Melvin、Balwinder S. Bhatti、Gary D. Byrd、Melanie N. Kiser、Christopher D. Hepler、Dawn N. Hooker、Jenny Zhang、Leslie A. Reynolds、Lisa R. Benson、Nikolai B. Fedorov、Serguei S. Sidach、J. Pike Mitchener、Linda M. Lucero、Ronald J. Lukas、Paul Whiteaker、Daniel Yohannes

  DOI：10.1021/jm3011299

  日期：2012.11.26

  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.