N-[4-(5-Chloro-2-methoxy-benzyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-yl]-C,C,C-trifluoro-methanesulfonamide | 693262-92-9

• 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: N-[4-(5-Chloro-2-methoxy-benzyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-yl]-C,C,C-trifluoro-methanesulfonamide
• 英文别名: N-[4-[(5-chloro-2-methoxyphenyl)methyl]-2-oxo-6-(trifluoromethyl)-1H-quinolin-3-yl]-1,1,1-trifluoromethanesulfonamide
• CAS: 693262-92-9
• 化学式: C₁₉H₁₃ClF₆N₂O₄S
• 分子量: 514.833
• InChiKey: CBCGLLDRSNNYJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-[4-(5-Chloro-2-methoxy-benzyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-yl]-C,C,C-trifluoro-methanesulfonamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 N-[4-(5-Chloro-2-hydroxy-benzyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-yl]-C,C,C-trifluoro-methanesulfonamide
  参考文献：
  名称：

  The synthesis and structure–activity relationships of 3-amino-4-benzylquinolin-2-ones

  摘要：

  3-Amino-4-benzylquinolin-2-ones have been identified as a novel class of KCNQ2 channel openers. Synthesis and SAR is described along with their electrophysiological evaluation as activators of the cloned mKCNQ2 channel expressed in Xenopus laevis oocytes. The preliminary SAR data suggest the importance of both the trifluoromethylsulfonamido group and electron-withdrawing substituents on the quinolone nucleus for expression of KCNQ2 channel opening properties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.073
• 作为产物：
  描述：

  4-(三氟甲基)苯基氨基甲酸叔丁酯 在 吡啶 、 盐酸 、 叔丁基锂 、 sodium acetate 、 三溴化硼 、 sodium hydride 、 一水合肼 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 生成 N-[4-(5-Chloro-2-methoxy-benzyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-yl]-C,C,C-trifluoro-methanesulfonamide
  参考文献：
  名称：

  The synthesis and structure–activity relationships of 3-amino-4-benzylquinolin-2-ones

  摘要：

  3-Amino-4-benzylquinolin-2-ones have been identified as a novel class of KCNQ2 channel openers. Synthesis and SAR is described along with their electrophysiological evaluation as activators of the cloned mKCNQ2 channel expressed in Xenopus laevis oocytes. The preliminary SAR data suggest the importance of both the trifluoromethylsulfonamido group and electron-withdrawing substituents on the quinolone nucleus for expression of KCNQ2 channel opening properties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.073

文献信息

• The synthesis and structure–activity relationships of 3-amino-4-benzylquinolin-2-ones
  作者：Piyasena Hewawasam、Nathan Chen、Min Ding、Joanne T. Natale、Christopher G. Boissard、Sarita Yeola、Valentin K. Gribkoff、John Starrett、Steven I. Dworetzky

  DOI：10.1016/j.bmcl.2004.01.073

  日期：2004.4

  3-Amino-4-benzylquinolin-2-ones have been identified as a novel class of KCNQ2 channel openers. Synthesis and SAR is described along with their electrophysiological evaluation as activators of the cloned mKCNQ2 channel expressed in Xenopus laevis oocytes. The preliminary SAR data suggest the importance of both the trifluoromethylsulfonamido group and electron-withdrawing substituents on the quinolone nucleus for expression of KCNQ2 channel opening properties. (C) 2004 Elsevier Ltd. All rights reserved.