6-methoxy-4-(trifluoromethyl)quinolin-2(1H)-one | 328956-13-4

• 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
• 英文名称: 6-methoxy-4-(trifluoromethyl)quinolin-2(1H)-one
• 英文别名: 6-methoxy-4-trifluoromethylquinolin-2(1H)-one；6-Methoxy-4-trifluoromethyl-2(1H)-quinolinone；6-Methoxy-4-(trifluoromethyl)-2-quinolinol；6-methoxy-4-(trifluoromethyl)-1H-quinolin-2-one
• CAS: 328956-13-4
• 化学式: C₁₁H₈F₃NO₂
• 分子量: 243.185
• InChiKey: PONNDNMHYHDVIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  5

反应信息

• 作为反应物：
  描述：

  6-methoxy-4-(trifluoromethyl)quinolin-2(1H)-one 在 氢溴酸 、 溶剂黄146 作用下， 反应 72.0h， 以70%的产率得到6-hydroxy-4-(trifluoromethyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function

  摘要：

  Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.016
• 作为产物：
  描述：

  4,4,4-三氟-3-氧代丁酸 、 甲氧苯胺 生成 6-methoxy-4-(trifluoromethyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Bicyclic androgen and progesterone receptor modulator compounds and methods

  摘要：

  本发明涉及化合物、药物组合物和调节由AR和PR介导的过程的方法。更具体地，本发明涉及非甾体化合物和组合物，这些化合物和组合物是高亲和力、高特异性的AR和PR的激动剂、部分激动剂（即部分激活剂和/或组织特异性激活剂）和拮抗剂。还提供了制备这种化合物和药物组合物的方法，以及在其合成中使用的关键中间体。

  公开号：

  US06566372B1

文献信息

• Syntheses and Fluorescent Properties of 6-Methoxy-2-oxoquinoline-3,4-dicarbonitriles and 6,7-Dimethoxy-2-oxoquinoline-3,4-dicarbonitriles
  作者：Guy Crépin Enoua、Günther Lahm、Georg Uray、Wolfgang Stadlbauer

  DOI：10.1002/jhet.1865

  日期：2014.8

  4-Chlorocarbostyrils , , , , with methoxy substituents in 6, 7, or 6,7-position react with potassium cyanide in a p-toluenesulfinate mediated reaction either to the highly fluorescent and stable 2-oxoquinoline-3,4-dicarbonitriles , , , or at slightly lower temperatures to 4-monocarbonitriles , , . 4-Chlorocarbostyril and lithium p-toluenesulfinate gave pure 4-toluenesulfonylquinolone , which reacted

  4-氯咔啉 ， ， ， ， 在6、7或6,7位的甲氧基取代基与 对甲苯磺酸酯介导的对高荧光和稳定的2-氧代喹啉-3,4-二腈的反应中的氰化钾， ， ， 或在较低的温度下生成4-单腈 ， ， 。4-氯卡巴斯蒂利 和 对甲苯磺酸锂得到纯的4-甲苯磺酰基喹诺酮与氰化钾反应生成单腈 或二腈 ，取决于反应条件。4-三氟甲基喹诺酮类 和 由合适的甲氧基苯胺和4,4,4-三氟乙酰乙酸制备用于荧光比较的样品。
• 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 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。
• [EN] QUINOLINE-BASED DERIVATIVES AS VAP-1 INHIBITORS<br/>[FR] DÉRIVÉS À BASE DE QUINOLÉINE UTILISÉS COMME INHIBITEURS DE VAP-1<br/>[ZH] 作为VAP-1抑制剂的喹啉类衍生物
  申请人：MEDSHINE DISCOVERY INC

  公开号：WO2020063854A1

  公开（公告）日：2020-04-02

  公开了一类喹啉类衍生物及其在制备治疗与VAP-1有关疾病的药物中的应用，具体公开了式（II）所示化合物及其药学上可接受的盐。
• BICYCLIC ANDROGEN AND PROGESTERONE RECEPTOR MODULATOR COMPOUNDS AND METHODS
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP1212303A2

  公开（公告）日：2002-06-12