2-(4-aminophenyl)-1-hydroxy-benzimidazole | 149845-64-7

• 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: 2-(4-aminophenyl)-1-hydroxy-benzimidazole
• 英文别名: 4-(1-Hydroxybenzimidazol-2-yl)aniline
• CAS: 149845-64-7
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: CGGVROKDSFBZDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  64.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-aminobenzyl-2-nitrophenylamine 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-aminophenyl)-1-hydroxy-benzimidazole
  参考文献：
  名称：

  N-Hydroxybenzimidazole Inhibitors of the Transcription Factor LcrF in Yersinia: Novel Antivirulence Agents

  摘要：

  LcrF, a multiple adaptational response (MAR) transcription factor, regulates virulence in Yersinia pestis and Yersinia pseudotuberculosis. In a search for small molecule inhibitors of LcrF, an acrylic amide series of N-hydroxybenzimidazoles was synthesized and the SAR (structure-activity relationship) was examined, Selected test compounds demonstrated inhibitory activity in a primary cell-free LcrF-DNA binding assay as well as in a secondary whole cell assay (type III secretion system dependent Y. pseudotuberculosis cytotoxicity assay). The inhibitors exhibited no measurable antibacterial activity in vitro, confirming that they do not target bacterial growth. These results demonstrate that N-hydroxy-benzimidazole inhibitors, exemplified by 14, 22, and 36, are effective antivirulence agents and have the potential to prevent infections caused by Yersinia spp.

  DOI：

  10.1021/jm9006577

文献信息

• Transcription factor modulating compounds and methods of use thereof
  申请人：Alekshun Michael N.

  公开号：US20090170812A1

  公开（公告）日：2009-07-02

  Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.

  提供了替代苯并咪唑化合物，可用作抗感染剂，可降低微生物的抗药性、毒力或生长。提供了制备和使用替代苯并咪唑化合物的方法，以及其中的药物制剂，例如用于减少抗生素抗性和抑制生物膜的制剂。
• JPH0525140A
  申请人：——

  公开号：JPH0525140A

  公开（公告）日：1993-02-02
• <i>N</i>-Hydroxybenzimidazole Inhibitors of the Transcription Factor LcrF in <i>Yersinia</i>: Novel Antivirulence Agents
  作者：Oak K. Kim、Lynne K. Garrity-Ryan、Victoria J. Bartlett、Mark C. Grier、Atul K. Verma、Gabriel Medjanis、Janice E. Donatelli、Ann B. Macone、S. Ken Tanaka、Stuart B. Levy、Michael N. Alekshun

  DOI：10.1021/jm9006577

  日期：2009.9.24

  LcrF, a multiple adaptational response (MAR) transcription factor, regulates virulence in Yersinia pestis and Yersinia pseudotuberculosis. In a search for small molecule inhibitors of LcrF, an acrylic amide series of N-hydroxybenzimidazoles was synthesized and the SAR (structure-activity relationship) was examined, Selected test compounds demonstrated inhibitory activity in a primary cell-free LcrF-DNA binding assay as well as in a secondary whole cell assay (type III secretion system dependent Y. pseudotuberculosis cytotoxicity assay). The inhibitors exhibited no measurable antibacterial activity in vitro, confirming that they do not target bacterial growth. These results demonstrate that N-hydroxy-benzimidazole inhibitors, exemplified by 14, 22, and 36, are effective antivirulence agents and have the potential to prevent infections caused by Yersinia spp.