5-fluoro-1-methyl-1H-benzo[d]imidazole-2-amine | 1156928-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-fluoro-1-methyl-1H-benzo[d]imidazole-2-amine
• 英文别名: 5-fluoro-1-methyl-1H-benzo[d]imidazol-2-amine；2-Amino-5-fluoro-1-methylbenzimidazole；5-fluoro-1-methylbenzimidazol-2-amine
• CAS: 1156928-67-4
• 化学式: C₈H₈FN₃
• mdl: MFCD11215483
• 分子量: 165.17
• InChiKey: XURFLYNSPWZPFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-fluoro-1-methyl-1H-benzo[d]imidazole-2-amine 在 二碘甲烷 、 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以30 %的产率得到5-Fluoro-2-iodo-1-methylbenzimidazole
  参考文献：
  名称：

  BENZIMIDAZOLE DERIVATIVES

  摘要：

  Disclosed are benzimidazole derivatives, pharmaceutical compositions comprising them, and methods of using them.

  公开号：

  WO2024130173A1
• 作为产物：
  描述：

  4-氟-2-硝基-N-甲基苯胺 在 氯化铵 、 锌 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 19.0h， 生成 5-fluoro-1-methyl-1H-benzo[d]imidazole-2-amine
  参考文献：
  名称：

  BENZIMIDAZOLE DERIVATIVES

  摘要：

  Disclosed are benzimidazole derivatives, pharmaceutical compositions comprising them, and methods of using them.

  公开号：

  WO2024130173A1

文献信息

• Photoreactivity of monofluorinated 2-azidobenzimidazoles towards carboxylic acids
  作者：Nils Eckhard Kanitz、Thomas Lindel

  DOI：10.1515/znb-2016-0195

  日期：2016.12.1

  Aiming at the development of new photolabeling agents, the synthesis and photoreactivity of all monofluorinated derivatives of 2-azido-1-methylbenzimidazole are described. In the case of 4-, 5-, or 7-fluorination, irradiation in the presence of carboxylic acids (300 nm, Rayonet) afforded the monofluorinated 2-amino-6-acyloxybenzimidazoles in a regioselective manner, presumably after conversion of the initially formed nitrene to the N-cyanodiazaxylylene. Incorporation of chloride was also possible, and yields were comparable to those observed for the non-fluorinated parent compound. When blocking the reactive 6-position by a fluoro substituent, the title reaction was not possible. The analysis of the ¹⁹F NMR chemical shifts of the 5- and 7-monofluorinated products allowed the distinction between carboxylates and other nucleophiles.

  摘要：针对新型光标记剂的开发，描述了所有单氟衍生物2-氮化-1-甲基苯并咪唑的合成和光反应性。在4-、5-或7-氟化的情况下，在存在羧酸的情况下照射（300纳米，Rayonet）产生了单氟化的2-氨基-6-酰氧基苯并咪唑，可能是在最初形成的亚氮烯转化为N-氰基二氮并之后。氯化物的引入也是可能的，并且产率与非氟化母体化合物观察到的产率相当。当通过氟代取代物阻塞反应性的6位时，标题反应不可能进行。对5-和7-单氟化产物的19F NMR化学位移的分析允许区分羧酸盐和其他亲核试剂。
• Pyrazole-amides and -sulfonamides
  申请人：Atkinson N. Robert

  公开号：US20050049237A1

  公开（公告）日：2005-03-03

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides pyrazole-amides and -sulfonamides, compositions and methods that are useful in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  本发明提供了一种通过抑制电压依赖性钠通道中的钠离子流来治疗疾病的化合物、组合物和方法。更具体地，本发明提供了吡唑酰胺和磺酰胺，以及其组合物和方法，这些化合物、组合物和方法对于治疗中枢或外周神经系统疾病特别是疼痛和慢性疼痛非常有用，通过阻止与所述疾病的发作或复发有关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制包括PN3亚基的通道中的离子流来治疗神经病理性或炎性疼痛。
• PYRAZOLE-AMIDES AND -SULFONAMIDES
  申请人：Atkinson N. Robert

  公开号：US20080064690A1

  公开（公告）日：2008-03-13

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides pyrazole-amides and -sulfonamides, compositions and methods that are useful in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  本发明提供了一种通过抑制电压依赖性钠通道中的钠离子通量来治疗疾病的化合物、组合物和方法。更具体地，本发明提供了嘧唑酰胺和磺酰胺、组合物和方法，用于治疗中枢或外周神经系统障碍，特别是疼痛和慢性疼痛，通过阻断与指示条件的发生或复发有关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制包括PN3亚单位的通道中的离子通量来治疗神经病理性或炎症性疼痛。
• PYRAZOLE-AMIDES FOR USE IN THE TREATMENT OF PAIN
  申请人：Icagen, Inc.

  公开号：EP1451160B1

  公开（公告）日：2010-01-13
• BENZIMIDAZOLE DERIVATIVES USEFUL AS TRPM8 CHANNEL MODULATORS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP2440295B1

  公开（公告）日：2013-07-24