4-羟基-8-(三氟甲氧基)-2-(三氟甲基)喹啉 | 306935-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 4-羟基-8-(三氟甲氧基)-2-(三氟甲基)喹啉
• 英文名称: 8-(trifluoromethoxyl)-2-(trifluoromethyl)-4-quinolinol
• 英文别名: 8-trifluoromethoxy-2-trifluoromethyl-4-quinolinol；8-trifluoromethoxy-2-trifluoromethyl-4-hydroxyquinoline；8-(trifluoromethoxy)-2-(trifluoromethyl)-1H-quinolin-4-one
• CAS: 306935-26-2
• 化学式: C₁₁H₅F₆NO₂
• 分子量: 297.157
• InChiKey: NPILHDIBEBFVPW-UHFFFAOYSA-N

物化性质

• 沸点：
  299.1±35.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Predicted)
• 溶解度：
  >44.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  9

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  4-羟基-8-(三氟甲氧基)-2-(三氟甲基)喹啉 在 四磷十氧化物 、 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以84%的产率得到4-bromo-8-(trifluoromethoxy)-2-(trifluoromethyl)quinoline
  参考文献：
  名称：

  Identification of 5-(Aryl/Heteroaryl)amino-4-quinolones as Potent Membrane-Disrupting Agents to Combat Antibiotic-Resistant Gram-Positive Bacteria

  摘要：

  Nosocomial infections caused by resistant Gram-positive organisms are on the rise, presumably due to a combination of factors including prolonged hospital exposure, increased use of invasive procedures, and pervasive antibiotic therapy. Although antibiotic stewardship and infection control measures are helpful, newer agents against multidrug-resistant (MDR) Gram-positive bacteria are urgently needed. Here, we describe our efforts that led to the identification of 5-amino-4-quinolone 111 with exceptionally potent Gram-positive activity with minimum inhibitory concentrations (MICs) ≤0.06 μg/mL against numerous clinical isolates. Preliminary mechanism of action and resistance studies demonstrate that the 5-amino-4-quinolones are bacteriostatic, do not select for resistance, and selectively disrupt bacterial membranes. While the precise molecular mechanism has not been elucidated, the lead compound is nontoxic displaying a therapeutic index greater than 500, is devoid of hemolytic activity, and has attractive physicochemical properties (clog P = 3.8, molecular weight (MW) = 441) that warrant further investigation of this promising antibacterial scaffold for the treatment of Gram-positive infections.

  DOI：

  10.1021/acs.jmedchem.2c01151
• 作为产物：
  描述：

  邻氨基三氟甲氧基苯 、 三氟乙酰乙酸乙酯 在 phosphorous pentoxide p-toluenesulfonic acid 作用下， 以51%的产率得到4-羟基-8-(三氟甲氧基)-2-(三氟甲基)喹啉
  参考文献：
  名称：

  [EN] ANTIBIOTIC COMPOSITIONS
  [FR] COMPOSITIONS ANTIBIOTIQUES

  摘要：

  本公开涉及具有抗微生物活性的化合物，包括这些化合物与β-内酰胺类抗生素结合的组合物，以及使用这些化合物和组合物的方法。

  公开号：

  WO2017136642A1

文献信息

• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HEPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099274A1

  公开（公告）日：2003-12-04

  Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

  丙型肝炎病毒抑制剂公开了具有以下通式：其中R1、R2、R3、R'、B、Y和X在描述中有所描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。
• Thiazolidine derivative and medicinal use thereof
  申请人：——

  公开号：US20040259883A1

  公开（公告）日：2004-12-23

  A thiazolidine derivative represented by the formula (I) 1 wherein each symbol is as defined in the specification, and a pharmaceutically acceptable salt thereof exhibit a potent DPP-IV inhibitory activity, and can be provided as an agent for the prophylaxis or treatment of diabetes, an agent for the prophylaxis or treatment of obesity and the like.

  一种噻唑啉衍生物，其化学式为(I)1，其中每个符号如规范中所定义，其药物可接受的盐具有强效的DPP-IV抑制活性，可作为糖尿病的预防或治疗剂，肥胖症的预防或治疗剂等。
• THIAZOLIDINE DERIVATIVES AND MEDICINAL USE THEREOF
  申请人：SAKASHITA Hiroshi

  公开号：US20070259880A1

  公开（公告）日：2007-11-08

  A thiazolidine derivative represented by the formula (I) wherein each symbol is as defined in the specification, and a pharmaceutically acceptable salt thereof exhibit a potent DPP-IV inhibitory activity, and can be provided as an agent for the prophylaxis or treatment of diabetes, an agent for the prophylaxis or treatment of obesity and the like.

  一种由式(I)所表示的噻唑啉衍生物，其中每个符号如规范中所定义，并且其药物可接受的盐表现出强效的DPP-IV抑制活性，可以作为预防或治疗糖尿病的药剂，预防或治疗肥胖等药剂。
• THIAZOLIDINE DERIVATIVE AND MEDICINAL USE THEREOF
  申请人：Mitsubishi Pharma Corporation

  公开号：EP1426366A1

  公开（公告）日：2004-06-09

  A thiazolidine derivative represented by the formula (I) wherein each symbol is as defined in the specification, and a pharmaceutically acceptable salt thereof exhibit a potent DPP-IV inhibitory activity, and can be provided as an agent for the prophylaxis or treatment of diabetes, an agent for the prophylaxis or treatment of obesity and the like.

  由式（I）表示的噻唑烷衍生物 其中各符号如说明书中所定义，其药学上可接受的盐具有强效的 DPP-IV 抑制活性，可作为预防或治疗糖尿病的制剂、预防或治疗肥胖症的制剂等。
• Hepatitis C Virus Inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：EP2340830A2

  公开（公告）日：2011-07-06

  Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  公开了具有通式：(I) 的丙型肝炎病毒抑制剂，其中 R1、R2、R3、R'、B、Y 和 X 已在说明中描述。还公开了包含这些化合物的组合物和使用这些化合物抑制 HCV 的方法。