[4-(2-amino-3H-imidazol-4-yl)phenyl]-3,5-difluorobenzamide hydrochloride | 1190333-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-(2-amino-3H-imidazol-4-yl)phenyl]-3,5-difluorobenzamide hydrochloride
• 英文别名: N-[4-(2-amino-1H-imidazol-5-yl)phenyl]-3,5-difluorobenzamide;hydrochloride
• CAS: 1190333-13-1
• 化学式: C₁₆H₁₂F₂N₄O*ClH
• 分子量: 350.755
• InChiKey: WASHJFNOCXJDQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-叠氮苯甲酰甲基溴 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 盐酸 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 76.5h， 生成 [4-(2-amino-3H-imidazol-4-yl)phenyl]-3,5-difluorobenzamide hydrochloride
  参考文献：
  名称：

  [EN] INHIBITION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-PHENYL DERIVATIVES
  [FR] INHIBITION DE BIOFILMS BACTÉRIENS PAR DES DÉRIVÉS D'IMIDAZOLE-PHÉNYLE

  摘要：

  本文提供了一种防止、去除和/或抑制生物膜形成的咪唑-苯衍生物化合物的披露，以及包含这些化合物的组合物、包含这些化合物的设备和使用这些化合物的方法。

  公开号：

  WO2009123753A1

文献信息

• Augmenting the Activity of Macrolide Adjuvants against <i>Acinetobacter baumannii</i>
  作者：Veronica B. Hubble、Kyle R. Bartholomew、Alexander W. Weig、Sara M. Brackett、Samantha L. Barlock、Anne E. Mattingly、Ansley M. Nemeth、Roberta J. Melander、Christian Melander

  DOI：10.1021/acsmedchemlett.0c00276

  日期：2020.9.10

  Approximately 1.7 million Americans develop hospital associated infections each year, resulting in more than 98,000 deaths. One of the main contributors to such infections is the Gram-negative pathogen Acinetobacter baumannii. Recently, it was reported that aryl 2-aminoimidazole (2-AI) compounds potentiate macrolide antibiotics against a highly virulent strain of A. baumannii, AB5075. The two lead compounds in that report increased clarithromycin (CLR) potency against AB5075 by 16-fold, lowering the minimum inhibitory concentration (MIC) from 32 to 2 mu g/mL at a concentration of 10 mu M. Herein, we report a structure-activity relationship study of a panel of derivatives structurally inspired by the previously reported aryl 2-AI leads. Substitutions around the core phenyl ring yielded a lead that potentiates clarithromycin by 64- and 32-fold against AB5075 at 10 and 7.5 mu M, exceeding the dose response of the original lead. Additional probing of the amide linker led to the discovery of two urea containing adjuvants that suppressed clarithromycin resistance in AB5075 by 64- and 128-fold at 7.5 mu M. Finally, the originally reported adjuvant was tested for its ability to suppress the evolution of resistance to clarithromycin over the course of nine consecutive days. At 30 mu M, the parent compound reduced the CLR MIC from 512 to 2 mu g/mL, demonstrating that the original lead remained active against a more CLR resistant strain of AB5075.
• Identification of aryl 2-aminoimidazoles as biofilm inhibitors in Gram-negative bacteria
  作者：Cynthia A. Bunders、Justin J. Richards、Christian Melander

  DOI：10.1016/j.bmcl.2010.04.042

  日期：2010.6

  The synthesis and biofilm inhibitory activity of a 30-member aryl amide 2-aminoimidazole library against the three biofilm forming Gram-negative bacteria Escherichia coli, Psuedomonas aeruginosa, and Acinetobacter baumannii is presented. The most active compound identified inhibits the formation of E. coli biofilms with an IC(50) of 5.2 mu M and was observed to be non-toxic to planktonic growth, demonstrating that analogues based on an aryl framework are viable options as biofilm inhibitors within the 2-aminoimidazole family. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] INHIBITION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-PHENYL DERIVATIVES<br/>[FR] INHIBITION DE BIOFILMS BACTÉRIENS PAR DES DÉRIVÉS D'IMIDAZOLE-PHÉNYLE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2009123753A1

  公开（公告）日：2009-10-08

  Disclosure is provided for imidazole-phenyl derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  本文提供了一种防止、去除和/或抑制生物膜形成的咪唑-苯衍生物化合物的披露，以及包含这些化合物的组合物、包含这些化合物的设备和使用这些化合物的方法。