3-acetyl-6-chloro-2-(4-chloroanilino)-8-(trifluoromethyl)-1H-quinolin-4-one | 1258725-31-3

• 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: 3-acetyl-6-chloro-2-(4-chloroanilino)-8-(trifluoromethyl)-1H-quinolin-4-one
• CAS: 1258725-31-3
• 化学式: C₁₈H₁₁Cl₂F₃N₂O₂
• 分子量: 415.199
• InChiKey: PNVHXAZOJZQBFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-Acetyl-6-chloro-2-methylsulfanyl-8-trifluoromethyl-1H-quinolin-4-one 在 双氧水 作用下， 以 溶剂黄146 、 邻二氯苯 为溶剂， 反应 48.0h， 生成 3-acetyl-6-chloro-2-(4-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

文献信息

• Identification of 3-acyl-2-phenylamino-1,4-dihydroquinolin-4-one derivatives as inhibitors of the phosphatase SerB653 in Porphyromonas gingivalis, implicated in periodontitis
  作者：Suk-Kyeong Jung、Youngkyung Ko、Keum Ran Yu、Ju Hee Kim、Joo-Youn Lee、Chong Hak Chae、Suk Ji、Chang Hyen Kim、Hyeon Kyu Lee、Eun Bok Choi、Bo Yeon Kim、Raymond L. Erikson、Sang J. Chung、Seung Jun Kim

  DOI：10.1016/j.bmcl.2012.01.011

  日期：2012.3

  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.