1-(4-fluorophenyl)benzimidazole-2-thione | 1038333-46-8

• 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: 1-(4-fluorophenyl)benzimidazole-2-thione
• 英文别名: 1-(4-fluorophenyl)-1H-1,3-benzodiazole-2-thiol；3-(4-fluorophenyl)-1H-benzimidazole-2-thione
• CAS: 1038333-46-8
• 化学式: C₁₃H₉FN₂S
• mdl: MFCD11202249
• 分子量: 244.292
• InChiKey: AJNDNJRXZKSEJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)benzimidazole-2-thione 、 2-bromo-N-(3,5-dichloropyridin-2-yl)propanamide 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-(3,5-dichloropyridin-2-yl)-2-((1-(4-fluorophenyl)-benzo[d]imidazol-2-yl)thio)propanamide
  参考文献：
  名称：

  Host-Directed Inhibitors of Myxoviruses: Synthesis and in Vitro Biochemical Evaluation

  摘要：

  Drugs targeted to viral proteins are highly vulnerable to the development of viral resistance. One little explored approach to the treatment of viral diseases is the development of agents that target host factors required for virus replication. Myxoviruses are predominantly associated with acute disease and, thus, ideally suited for this approach since the necessary treatment time is anticipated to be limited. High-throughput screening previously identified benzimidazole 22407448 with broad antiviral activity against different influenza virus and paramyxovirus strains. Hit to lead chemistry has generated 6p (JMN3-003) with potent antiviral activity against a panel of myxovirus family members exhibiting EC(50) values in the low nanomolar range.

  DOI：

  10.1021/ml200125r
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 2.0h， 生成 1-(4-fluorophenyl)benzimidazole-2-thione
  参考文献：
  名称：

  Copper(I)-Catalyzed Synthesis of Substituted 2-Mercapto Benzimidazoles

  摘要：

  An efficient method for the preparation of various substituted 2-mercapto benzimidazoles from their corresponding thioureas has been developed. S-Alkylation of thioureas followed by Cu-catalyzed intramolecular N-arylation furnished substituted 2-mercapto benzimidazoles in high yields and short reaction times. Furthermore, 2-mercapto benzimidazoles substituted with a p-methoxybenzyl group allowed access to benzimidazole thiones.

  DOI：

  10.1021/jo802589d

文献信息

• Host-Directed Inhibitors of Myxoviruses: Synthesis and in Vitro Biochemical Evaluation
  作者：Aiming Sun、J. Maina Ndungu、Stefanie A. Krumm、Jeong-Joong Yoon、Pahk Thepchatri、Michael Natchus、Richard K. Plemper、James P. Snyder

  DOI：10.1021/ml200125r

  日期：2011.11.10

  Drugs targeted to viral proteins are highly vulnerable to the development of viral resistance. One little explored approach to the treatment of viral diseases is the development of agents that target host factors required for virus replication. Myxoviruses are predominantly associated with acute disease and, thus, ideally suited for this approach since the necessary treatment time is anticipated to be limited. High-throughput screening previously identified benzimidazole 22407448 with broad antiviral activity against different influenza virus and paramyxovirus strains. Hit to lead chemistry has generated 6p (JMN3-003) with potent antiviral activity against a panel of myxovirus family members exhibiting EC(50) values in the low nanomolar range.
• Copper(I)-Catalyzed Synthesis of Substituted 2-Mercapto Benzimidazoles
  作者：Siva Murru、Bhisma K. Patel、Jean Le Bras、Jacques Muzart

  DOI：10.1021/jo802589d

  日期：2009.3.6

  An efficient method for the preparation of various substituted 2-mercapto benzimidazoles from their corresponding thioureas has been developed. S-Alkylation of thioureas followed by Cu-catalyzed intramolecular N-arylation furnished substituted 2-mercapto benzimidazoles in high yields and short reaction times. Furthermore, 2-mercapto benzimidazoles substituted with a p-methoxybenzyl group allowed access to benzimidazole thiones.