3-(2-(Trifluoromethyl)phenoxy)benzaldehyde | 110728-50-2

• 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: 3-(2-(Trifluoromethyl)phenoxy)benzaldehyde
• 英文别名: 3-[2-(trifluoromethyl)phenoxy]benzaldehyde
• CAS: 110728-50-2
• 化学式: C₁₄H₉F₃O₂
• mdl: MFCD19060549
• 分子量: 266.219
• InChiKey: PGBSAFISOYKCJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  磷酰基乙酸三乙酯 、 3-(2-(Trifluoromethyl)phenoxy)benzaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Phosphonosulfonates Are Potent, Selective Inhibitors of Dehydrosqualene Synthase and Staphyloxanthin Biosynthesis in Staphylococcus aureus

  摘要：

  Staphylococcus aureus produces a golden carotenoid virulence factor called staphyloxanthin (STX), and we report here the inhibition of the enzyme, dehydrosqualene synthase (CrtM), responsible for the first committed step in STX biosynthesis. The most active compounds are halogen-substituted phosphonosulfonates, with K-i values as low as 5 nM against the enzyme and IC50 values for STX inhibition in S. aureus as low as 11 nM. There is, however, only a poor correlation (R-2 = 0.27) between enzyme and cell pIC(50) (= -log(10) IC50) values. The ability to predict cell from enzyme data improves considerably (to R-2 = 0.72) with addition of two more descriptors. We also investigated the activity of these compounds against human squalene synthase (SQS), as a counterscreen, finding several potent STX biosynthesis inhibitors with essentially no squalene synthase activity. These results open up the way to developing potent and selective inhibitors of an important virulence factor in S. aureus, a major human pathogen.

  DOI：

  10.1021/jm801023u
• 作为产物：
  描述：

  2-碘三氟甲基苯 、 间羟基苯甲醛 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 3-(2-(Trifluoromethyl)phenoxy)benzaldehyde
  参考文献：
  名称：

  Phosphonosulfonates Are Potent, Selective Inhibitors of Dehydrosqualene Synthase and Staphyloxanthin Biosynthesis in Staphylococcus aureus

  摘要：

  Staphylococcus aureus produces a golden carotenoid virulence factor called staphyloxanthin (STX), and we report here the inhibition of the enzyme, dehydrosqualene synthase (CrtM), responsible for the first committed step in STX biosynthesis. The most active compounds are halogen-substituted phosphonosulfonates, with K-i values as low as 5 nM against the enzyme and IC50 values for STX inhibition in S. aureus as low as 11 nM. There is, however, only a poor correlation (R-2 = 0.27) between enzyme and cell pIC(50) (= -log(10) IC50) values. The ability to predict cell from enzyme data improves considerably (to R-2 = 0.72) with addition of two more descriptors. We also investigated the activity of these compounds against human squalene synthase (SQS), as a counterscreen, finding several potent STX biosynthesis inhibitors with essentially no squalene synthase activity. These results open up the way to developing potent and selective inhibitors of an important virulence factor in S. aureus, a major human pathogen.

  DOI：

  10.1021/jm801023u

文献信息

• Compounds, pharmaceutical compositions and methods of use therefor
  申请人：Ghosh Shomir

  公开号：US20050143372A1

  公开（公告）日：2005-06-30

  The invention relates to compounds having the formula (I). Preferred compounds are antagonists of C—C chemokine receptor 8. The invention also relates to a method for treating a subjected having an inflammatory disorder or viral disorder comprising administering to a subject in need thereof an effective amount of a compound of the invention.

  该发明涉及具有公式（I）的化合物。首选化合物是C-C趋化因子受体8的拮抗剂。该发明还涉及一种治疗患有炎症性疾病或病毒性疾病的受试者的方法，该方法包括向需要的受试者施用该发明的化合物的有效量。
• Phosphonosulfonates Are Potent, Selective Inhibitors of Dehydrosqualene Synthase and Staphyloxanthin Biosynthesis in <i>Staphylococcus aureus</i>
  作者：Yongcheng Song、Fu-Yang Lin、Fenglin Yin、Mary Hensler、Carlos A. Rodrígues Poveda、Dushyant Mukkamala、Rong Cao、Hong Wang、Craig T. Morita、Dolores González Pacanowska、Victor Nizet、Eric Oldfield

  DOI：10.1021/jm801023u

  日期：2009.2.26

  Staphylococcus aureus produces a golden carotenoid virulence factor called staphyloxanthin (STX), and we report here the inhibition of the enzyme, dehydrosqualene synthase (CrtM), responsible for the first committed step in STX biosynthesis. The most active compounds are halogen-substituted phosphonosulfonates, with K-i values as low as 5 nM against the enzyme and IC50 values for STX inhibition in S. aureus as low as 11 nM. There is, however, only a poor correlation (R-2 = 0.27) between enzyme and cell pIC(50) (= -log(10) IC50) values. The ability to predict cell from enzyme data improves considerably (to R-2 = 0.72) with addition of two more descriptors. We also investigated the activity of these compounds against human squalene synthase (SQS), as a counterscreen, finding several potent STX biosynthesis inhibitors with essentially no squalene synthase activity. These results open up the way to developing potent and selective inhibitors of an important virulence factor in S. aureus, a major human pathogen.