4-(5-anthracen-9-yl-3-trifluoromethyl-pyrazol-1-yl)-benzonitrile | 1374744-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-(5-anthracen-9-yl-3-trifluoromethyl-pyrazol-1-yl)-benzonitrile
• 英文别名: 4-[5-Anthracen-9-yl-3-(trifluoromethyl)pyrazol-1-yl]benzonitrile；4-[5-anthracen-9-yl-3-(trifluoromethyl)pyrazol-1-yl]benzonitrile
• CAS: 1374744-78-1
• 化学式: C₂₅H₁₄F₃N₃
• 分子量: 413.401
• InChiKey: OBMGGZOGXYLDCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-anthracen-9-yl-3-trifluoromethyl-pyrazol-1-yl)-benzonitrile 在 双氧水 、 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以82%的产率得到4-(5-anthracen-9-yl-3-trifluoromethyl-pyrazol-1-yl)-benzamide
  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：

  9-乙酰基蒽 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 4-(5-anthracen-9-yl-3-trifluoromethyl-pyrazol-1-yl)-benzonitrile
  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-STAPHYLOCOCCAL CELECOXIB DERIVATIVES
  申请人：The Ohio State University Research Foundation

  公开号：EP2635274B1

  公开（公告）日：2017-12-06
• US9079899B2
  申请人：——

  公开号：US9079899B2

  公开（公告）日：2015-07-14
• [EN] ANTI-STAPHYLOCOCCAL CELECOXIB DERIVATIVES<br/>[FR] DÉRIVÉS DE CÉLÉCOXIB ANTI-STAPHYLOCOQUE
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2012061260A1

  公开（公告）日：2012-05-10

  A method of treating infection by Staphylococcus in a subject by administering a pharmaceutical composition including a celecoxib derivative of formula I or a pharmaceutically acceptable salt thereof is described. The preparation of numerous celecoxib derivatives for testing as potential anti-staphylococcal agents is also described.
• Development of novel antibacterial agents against methicillin-resistant Staphylococcus aureus
  作者：Hao-Chieh Chiu、Su-Lin Lee、Naval Kapuriya、Dasheng Wang、Yi-Ru Chen、Sung-Liang Yu、Samuel K. Kulp、Lee-Jene Teng、Ching-Shih Chen

  DOI：10.1016/j.bmc.2012.06.018

  日期：2012.8

  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.