2,6-dichloro-3H-imidazo[4,5-b]pyridine | 19918-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,6-dichloro-3H-imidazo[4,5-b]pyridine
• 英文别名: 2,6-Dichlor-3H-imidazo<4,5-b>pyridin；2,6-dichloro-1H-imidazo[4,5-b]pyridine
• CAS: 19918-35-5
• 化学式: C₆H₃Cl₂N₃
• 分子量: 188.016
• InChiKey: YCBVVLXZVZADHK-UHFFFAOYSA-N

物化性质

• 熔点：
  295-310 °C(Solv: water (7732-18-5); acetic acid (64-19-7))
• 沸点：
  232.4±50.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'-azaspiro[oxirane-2,3'-bicyclo[2.2.2]octan]-1'-yl-4-ium)trihydroborate 、 2,6-dichloro-3H-imidazo[4,5-b]pyridine 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 反应 73.25h， 生成 7-chloro-3H-1'-azaspiro[oxazolo[2',3':2,3]imidazo[4,5-b]pyridine-2,3'-bicyclo[2.2.2]octane]
  参考文献：
  名称：

  [EN] QUINUCLIDINE COMPOUNDS AS ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS
  [FR] COMPOSÉS QUINUCLIDINE EN TANT QUE LIGANDS DU RÉCEPTEUR NICOTINIQUE ALPHA-7 DE L'ACÉTYLCHOLINE

  摘要：

  揭示了一系列具有化学式（I）的喹诺啉类化合物，它们与尼古丁型α7受体结合，可能对中枢神经系统疾病的治疗有用。

  公开号：

  WO2016073407A1
• 作为产物：
  描述：

  6-氯-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮 在 三氯氧磷 作用下， 反应 12.0h， 以30%的产率得到2,6-dichloro-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Optimization of 5-substituted thiazolyl ureas and 6-substituted imidazopyridines as potential HIV-1 latency reversing agents

  摘要：

  A persistent latent reservoir of virus in CD4(+) T cells is a major barrier to cure HIV. Activating viral transcription in latently infected cells using small molecules is one strategy being explored to eliminate latency. We previously described the use of a FlpIn.FM HEK293 cellular assay to identify and then optimize the 2-acylaminothiazole class to exhibit modest activation of HIV gene expression. Here, we implement two strategies to further improve the activation of viral gene expression and physicochemical properties of this class. Firstly, we explored rigidification of the central oxy-carbon linker with a variety of saturated heterocycles, and secondly, investigated bioisosteric replacement of the 2-acylaminothiazole moiety. The optimization process afforded lead compounds (74 and 91) from the 2-piperazinyl thiazolyl urea and the imidazopyridine class. The lead compounds from each class demonstrate potent activation of HIV gene expression in the FlpIn.FM HEK293 cellular assay (both with LTR EC(50)s of 80 nM) and in the Jurkat Latency 10.6 cell model (LTR EC50 220 and 320 nM respectively), but consequently activate gene expression non-specifically in the FlpIn.FM HEK293 cellular assay (CMV EC50 70 and 270 nM respectively) manifesting in cellular cytotoxicity. The lead compounds have potential for further development as novel latency reversing agents. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112254

文献信息

• Quinuclidine compounds as α-7 nicotinic acetylcholine receptor ligands
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10174052B2

  公开（公告）日：2019-01-08

  There are disclosed a series of quinuclidines having the Formula (I), which bind to the nicotinic α7 receptor and may be useful for the treatment of disorders of the central nervous system.

  本研究公开了一系列具有式（I）的喹烯酮类化合物，它们与烟碱α7 受体结合，可用于治疗中枢神经系统疾病。
• QUINUCLIDINE COMPOUNDS AS ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3215512A1

  公开（公告）日：2017-09-13
• IMIDAZO[4,5-B]PYRIDINE DERIVATIVES AS PCSK9 INHIBITORS AND METHODS OF USE THEREOF
  申请人：[en]ASTRAZENECA AB

  公开号：WO2024126773A1

  公开（公告）日：2024-06-20

  A compound with the Formula (I): A-B-C wherein A is of the following formula (AA) and X1is selected from O, S or NH; X2is either N or C-H; X3is either N or C-RA3; wherein if X1is NH and X2is C-H then X3is C-RA3; B is of formula (B-1) or (B-2); C is selected from the group consisting of optionally substituted C6-10carboaryl, C5-6heteroaryl or C5-10heterocyclyl, and their use as PCSK9 inhibitors.