N-[4-(5-p-tolyl-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-aminosulfonamide | 1374744-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[4-(5-p-tolyl-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-aminosulfonamide
• 英文别名: 5-(4-Methylphenyl)-1-[4-(sulfamoylamino)phenyl]-3-(trifluoromethyl)pyrazole
• CAS: 1374744-71-4
• 化学式: C₁₇H₁₅F₃N₄O₂S
• 分子量: 396.393
• InChiKey: SHGXCCXQSBQHLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(4-nitrophenyl)-5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazole 在 platinum(IV) oxide 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[4-(5-p-tolyl-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

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
• ANTIBACTERIAL PROTEIN KINASE INHIBITORS
  申请人：The Ohio State University

  公开号：EP2879679A2

  公开（公告）日：2015-06-10
• US9079899B2
  申请人：——

  公开号：US9079899B2

  公开（公告）日：2015-07-14
• US9457031B2
  申请人：——

  公开号：US9457031B2

  公开（公告）日：2016-10-04
• [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.