4-[5-(4'-Bromo-biphenyl-4-yl)-3-trifluoromethyl-pyrazol-1-yl]-phenylamine | 1177469-55-4

• 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-[5-(4'-Bromo-biphenyl-4-yl)-3-trifluoromethyl-pyrazol-1-yl]-phenylamine
• 英文别名: 4-[5-[4-(4-Bromophenyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]aniline
• CAS: 1177469-55-4
• 化学式: C₂₂H₁₅BrF₃N₃
• 分子量: 458.28
• InChiKey: FGBYYIZFRTUYTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[5-(4'-Bromo-biphenyl-4-yl)-3-trifluoromethyl-pyrazol-1-yl]-phenylamine 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-{4-[5-(4'-Bromo-biphenyl-4-yl)-3-trifluoromethyl-pyrazol-1-yl]-phenyl}-aminosulfonamide
  参考文献：
  名称：

  Development of novel antibacterial agents against methicillin-resistant Staphylococcus aureus

  摘要：

  Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to public health because of its resistance to multiple antibiotics most commonly used to treat infection. In this study, we report the unique ability of the cyclooxygenase-2 (COX-2) inhibitor celecoxib to kill Staphylococcus aureus and MRSA with modest potency. We hypothesize that the anti-Staphylococcus activity of celecoxib could be pharmacologically exploited to develop novel anti-MRSA agents with a distinct mechanism. Examination of an in-house, celecoxib-based focused compound library in conjunction with structural modifications led to the identification of compound 46 as the lead agent with high antibacterial potency against a panel of Staphylococcus pathogens and different strains of MRSA. Moreover, this killing effect is bacteria-specific, as human cancer cells are resistant to 46. In addition, a single intraperitoneal administration of compound 46 at 30 mg/kg improved the survival of MRSA-infected C57BL/6 mice. In light of its high potency in eradicating MRSA in vitro and its in vivo activity, compound 46 and its analogues warrant continued preclinical development as a potential therapeutic intervention against MRSA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.018
• 作为产物：
  描述：

  4-乙酰基-4-溴代联苯 在 盐酸 、 platinum(IV) oxide 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 4-[5-(4'-Bromo-biphenyl-4-yl)-3-trifluoromethyl-pyrazol-1-yl]-phenylamine
  参考文献：
  名称：

  Development of novel antibacterial agents against methicillin-resistant Staphylococcus aureus

  摘要：

  Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to public health because of its resistance to multiple antibiotics most commonly used to treat infection. In this study, we report the unique ability of the cyclooxygenase-2 (COX-2) inhibitor celecoxib to kill Staphylococcus aureus and MRSA with modest potency. We hypothesize that the anti-Staphylococcus activity of celecoxib could be pharmacologically exploited to develop novel anti-MRSA agents with a distinct mechanism. Examination of an in-house, celecoxib-based focused compound library in conjunction with structural modifications led to the identification of compound 46 as the lead agent with high antibacterial potency against a panel of Staphylococcus pathogens and different strains of MRSA. Moreover, this killing effect is bacteria-specific, as human cancer cells are resistant to 46. In addition, a single intraperitoneal administration of compound 46 at 30 mg/kg improved the survival of MRSA-infected C57BL/6 mice. In light of its high potency in eradicating MRSA in vitro and its in vivo activity, compound 46 and its analogues warrant continued preclinical development as a potential therapeutic intervention against MRSA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.018

文献信息

• ANTI-FRANCISELLA AGENTS
  申请人：Chen Ching-Shih

  公开号：US20120108823A1

  公开（公告）日：2012-05-03

  A series of celecoxib derivatives defined by Formula I: were prepared and evaluated for their ability to inhibit the gram-negative bacteria Francisella tularensis . Pharmaceutical compositions including celecoxib derivatives and their use in methods for treating or preventing infection by Francisella tularensis in a subject are described.

  一系列由公式I定义的Celecoxib衍生物被制备并评估其抑制革兰氏阴性细菌Francisella tularensis的能力。描述了包括Celecoxib衍生物的制药组合物及其在治疗或预防受体内Francisella tularensis感染的方法中的使用。
• Pyrazole derivatives as anti-francisella agents
  申请人：The Ohio State University Research Foundation

  公开号：EP2246332B1

  公开（公告）日：2013-09-18
• ANTIBACTERIAL PROTEIN KINASE INHIBITORS
  申请人：The Ohio State University

  公开号：US20150258100A1

  公开（公告）日：2015-09-17

  Methods of treating bacterial infection by in a subject by administering a pharmaceutical composition including a celecoxib derivative are described. The compounds are particularly useful for treating infection by bacteria capable of growing inside macrophages, such as Myocobacteria tuberculosis.
• US8580827B2
  申请人：——

  公开号：US8580827B2

  公开（公告）日：2013-11-12
• US9457031B2
  申请人：——

  公开号：US9457031B2

  公开（公告）日：2016-10-04