6-chloro-8-trifluoromethyl-2-methylsulfinyl-3-acetyl-1H-quinolin-4-one | 1046459-73-7

• 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: 6-chloro-8-trifluoromethyl-2-methylsulfinyl-3-acetyl-1H-quinolin-4-one
• CAS: 1046459-73-7
• 化学式: C₁₃H₉ClF₃NO₃S
• 分子量: 351.734
• InChiKey: AFCRKCSIGWCJRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.0
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-chloro-8-trifluoromethyl-2-methylsulfinyl-3-acetyl-1H-quinolin-4-one 、 邻氯苯胺 以 邻二氯苯 为溶剂， 反应 24.0h， 生成 3-acetyl-6-chloro-2-(2-chloroanilino)-8-(trifluoromethyl)-1H-quinolin-4-one
  参考文献：
  名称：

  Identification of 3-acyl-2-phenylamino-1,4-dihydroquinolin-4-one derivatives as inhibitors of the phosphatase SerB653 in Porphyromonas gingivalis, implicated in periodontitis

  摘要：

  The serine phosphatase SerB653 plays a crucial role in the infection of Porphyromonas gingivalis, which contributes to the pathogenesis of periodontitis, an inflammatory disease of teeth-supporting tissues. Because functional loss of SerB653 eliminates the virulence of P. gingivalis, SerB653 inhibitors are considered potential periodontitis therapeutic or preventive agents. To identify SerB653 inhibitors with potent anti-periodontitis activity, we conducted a high-throughput screen of a representative 6800-compound subset of a synthetic chemical library of the Korea Chemical Bank (KCB) for compounds with activity against SerB653. The primary screening yielded 150 hits, and subsequent confirmatory studies identified eight compounds, mainly within a single cluster of 3-acyl-2-phenylamino-1,4-dihydroquinolin-4-one derivatives, that showed greater than 50% inhibition of SerB653 activity at a concentration of 50 mu M. A second screening with a focused library identified 10 compounds with IC50 values less than 10 mu M. In antibacterial tests, three of these compounds showed a minimum inhibitory concentration against P. gingivalis growth of 5-50 nM. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.011
• 作为产物：
  描述：

  3-Acetyl-6-chloro-2-methylsulfanyl-8-trifluoromethyl-1H-quinolin-4-one 在 双氧水 、 溶剂黄146 作用下， 反应 24.0h， 以89%的产率得到6-chloro-8-trifluoromethyl-2-methylsulfinyl-3-acetyl-1H-quinolin-4-one
  参考文献：
  名称：

  合成高度官能化的2-和4-氨基喹啉衍生物的方法

  摘要：

  一种用于2-和4-氨基喹啉衍生物的合成方法，这需要-2-甲硫基- 3-酰基-1的2-或4-取代基的选择性激活的优点ħ -喹啉-4-酮1，已经研制成功。由于先前已描述了由4-喹啉酮1形成3-氨基喹啉酮的方法，因此新方法包括从普通的4-喹啉酮开始选择性合成三种异构的2-，3-和4-氨基喹啉衍生物的通用方法。1。

  DOI：

  10.1016/j.tet.2008.05.014