(2E)-N-(4-cyanophenyl)-3-(4-fluorophenyl)prop-2-enamide | 1187839-97-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-N-(4-cyanophenyl)-3-(4-fluorophenyl)prop-2-enamide
• 英文别名: (E)-N-(4-cyanophenyl)-3-(4-fluorophenyl)prop-2-enamide
• CAS: 1187839-97-9
• 化学式: C₁₆H₁₁FN₂O
• 分子量: 266.275
• InChiKey: FZUWZIWJNLVQHA-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-N-(4-cyanophenyl)-3-(4-fluorophenyl)prop-2-enamide 在 镍 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.5h， 生成 (E)-N-[4-(aminomethyl)phenyl]-3-(4-fluorophenyl)prop-2-enamide
  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
• 作为产物：
  描述：

  对氟肉桂酰氯 、 对氨基苯腈 生成 (2E)-N-(4-cyanophenyl)-3-(4-fluorophenyl)prop-2-enamide
  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

• <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.