7-甲氧基-2-(三氟甲基)喹啉-4-醇 | 41192-85-2

• 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: 7-甲氧基-2-(三氟甲基)喹啉-4-醇
• 中文别名: 7-甲氧基-4-羟基-2-三氟甲基喹啉
• 英文名称: 7-methoxy-2-trifluoromethyl-1H-quinolin-4-one
• 英文别名: 4-hydroxy-7-methoxy-2-trifluoromethylquinoline；7-Methoxy-2-(trifluoromethyl)quinolin-4-OL；7-methoxy-2-(trifluoromethyl)-1H-quinolin-4-one
• CAS: 41192-85-2
• 化学式: C₁₁H₈F₃NO₂
• 分子量: 243.185
• InChiKey: SOHIYSRJLNWZFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  339.9±37.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 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：
  6

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  7-甲氧基-2-(三氟甲基)喹啉-4-醇 在 三氯氧磷 作用下， 反应 2.0h， 以78 mg的产率得到4-chloro-7-methoxy-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：

  间氨基苯甲醚 、 三氟乙酰乙酸乙酯 在 polyphosphoric acid 作用下， 反应 4.0h， 以12%的产率得到7-甲氧基-2-(三氟甲基)喹啉-4-醇
  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

文献信息

• Proline derivatives and use thereof as drugs
  申请人：Kitajima Hiroshi

  公开号：US20050245538A1

  公开（公告）日：2005-11-03

  The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

  本发明旨在提供具有治疗效果的化合物，其作用是通过DPP-IV的抑制作用，并且作为药物产品具有令人满意的效果。本发明人发现，在丙氨酸的γ位上引入取代基的衍生物具有强效的DPP-IV抑制活性，并通过增加稳定性完成了本发明。
• Proline derivatives and the use thereof as drugs
  申请人：——

  公开号：US20040106655A1

  公开（公告）日：2004-06-03

  The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the &ggr;-position of proline represented by the formula (I) 1 wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

  本发明旨在提供具有治疗作用的化合物，由于DPP-IV抑制作用而具有满意的药物产品。本发明人发现，具有引入取代基的脯氨酸γ-位置的衍生物，其化学式为(I)1，其中每个符号如规范中所定义，具有强效的DPP-IV抑制活性，并通过增加稳定性完成了本发明。
• PROLINE DERIVATIVES AND USE THEREOF AS DRUGS
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP1308439B1

  公开（公告）日：2008-10-15
• Antibacterial pyrimidine compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0096214B1

  公开（公告）日：1991-02-27
• Antimalarials. 2. Dihydro-1,3-oxazinoquinolines and dihydro-1,3-pyridobenzoxazines
  作者：L. C. March、W. A. Romanchick、G. S. Bajwa、M. M. Joullie

  DOI：10.1021/jm00262a006

  日期：1973.4