4-(5-chloro-2-methoxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-2(1H)-quinolinone | 275375-70-7

• 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: 4-(5-chloro-2-methoxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-2(1H)-quinolinone
• 英文别名: 4-(5-chloro-2-methoxyphenyl)-3-(2-hydroxyethyl)-6-trifluoromethyl-2(1H)-quinolinone；3-(2-Hydroxyethyl)-4-(2-methoxy-5-chlorophenyl)-6-(trifluoromethyl)-1,2-dihydroquinoline-2-one；4-(5-chloro-2-methoxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-1H-quinolin-2-one
• CAS: 275375-70-7
• 化学式: C₁₉H₁₅ClF₃NO₃
• 分子量: 397.781
• InChiKey: HDBWMDUCFAXJCN-UHFFFAOYSA-N

物化性质

• 熔点：
  219-221 °C
• 沸点：
  554.8±50.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(5-chloro-2-methoxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-2(1H)-quinolinone 生成 BMS-223131
  参考文献：
  名称：

  A mild and efficient synthesis of 4-aryl-quinolin-2(1H)-ones via a tandem amidation/Knoevenagel condensation of 2-amino-benzophenones with esters or lactones

  摘要：

  Using LiHMDS as the base, a tandem amidation/Knoevenagel condensation of 2-aminobenzophenones with alpha-methylene esters or lactones gives 4-aryl-quinolin-2(1H)-ones in 65-96% yield. This method is mild, highly efficient, and amenable to scaleup. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00889-x
• 作为产物：
  描述：

  (2-氨基-5-三氟甲基-苯基)-(5-氯-2-甲氧基-苯基)-甲酮 在 吡啶 、 dimethyl sulfide borane 、 氢溴酸 、 双(三甲基硅烷基)氨基钾 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-(5-chloro-2-methoxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-2(1H)-quinolinone
  参考文献：
  名称：

  4-Aryl-3-(hydroxyalkyl)quinolin-2-ones:  Novel Maxi-K Channel Opening Relaxants of Corporal Smooth Muscle Targeted for Erectile Dysfunction

  摘要：

  Novel 4-aryl-3-(hydroxyalkyl)quinoline-2-one derivatives were prepared and evaluated as openers of the cloned maxi-K channel hSlo expressed in Xenopus laevis oocytes by utilizing electrophysiological methods. The effect of these maxi-K openers on corporal smooth muscle was studied in vitro using isolated rabbit corpus cavernosum. From this study, a potent maxi-K opener was identified as an effective relaxant of rabbit corporal smooth muscle and shown to be active in an in vivo animal model of male erectile function.

  DOI：

  10.1021/jm030005h

文献信息

• Preparation of 3-substituted-4-arylquinolin-2-one derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US06353119B1

  公开（公告）日：2002-03-05

  The present invention relates to a process for the preparation of 3-substituted-4-arylquinolin-2-one derivatives from a substituted coumarin and using a photochemical cyclization method on a dihydrofuran intermediate.

  本发明涉及一种从取代香豆素出发，利用二氢呋喃中间体的光化学环化方法制备3-取代-4-芳基喹啉-2-酮衍生物的工艺。
• [EN] 3-SUBSTITUTED-4-ARYLQUINOLIN-2-ONE DERIVATIVES AS POTASSIUM CHANNEL MODULATORS<br/>[FR] DERIVES 3-SUBSTITUES DE 4-ARYLQUINOLIN-2-ONE UTILISES COMME MODULATEURS DES CANAUX POTASSIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2000034244A1

  公开（公告）日：2000-06-15

  The present invention provides novel 3-substituted-4-arylquinolin-2-one derivatives having general formula (I) wherein R, R?1, R2, R3, R4, R5, R6 and R7¿ are as defined herein, or a nontoxic pharmaceutically acceptable salt thereof which are modulators of the large conductance calcium-activated K+ channels and are useful in the treatment of disorders which are responsive to the opening of the potassium channels.

  本发明提供了一种新型的3-取代-4-芳基喹啉-2-酮衍生物，其具有通式（I），其中R，R?1，R2，R3，R4，R5，R6和R7¿如本文所定义，或其无毒的药学上可接受的盐，它们是大电导钙激活K+通道的调节剂，并且在治疗对钾通道开放有反应的疾病方面很有用。
• 3-SUBSTITUTED-4-ARYLQUINOLIN-2-ONE DERIVATIVES AS POTASSIUM CHANNEL MODULATORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1133474B1

  公开（公告）日：2007-02-21
• EP1133474A4
  申请人：——

  公开号：EP1133474A4

  公开（公告）日：2005-02-16
• US6184231B1
  申请人：——

  公开号：US6184231B1

  公开（公告）日：2001-02-06