8-benzoyl-2-(4-(methylsulfonyl)phenyl)quinoline-4-carboxylic acid | 1242077-98-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 8-benzoyl-2-(4-(methylsulfonyl)phenyl)quinoline-4-carboxylic acid
• 英文别名: 8-benzoyl-2-(4-methylsulfonylphenyl)quinoline-4-carboxylic acid
• CAS: 1242077-98-0
• 化学式: C₂₄H₁₇NO₅S
• 分子量: 431.469
• InChiKey: NMIJKSWDGCIHBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-benzoyl-2-(4-(methylthio)phenyl)quinoline-4-carboxylic acid 在 Oxone 作用下， 以 四氢呋喃 、 水 为溶剂， 以67%的产率得到8-benzoyl-2-(4-(methylsulfonyl)phenyl)quinoline-4-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of ketoprofen analogs as potent cyclooxygenase-2 inhibitors

  摘要：

  A new series of ketoprofen analogs were synthesized to evaluate their biological activities as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 inhibition studies showed that all compounds were potent and selective inhibitors of the COX-2 isozyme with IC(50) values in the highly potent 0.057-0.085 mu M range, and COX-2 selectivity indexes in the 115 to >1298.7 range. Compounds possessing azido pharmacophore group (8a and 8b) exhibited highly COX-2 inhibitory selectivity and potency even more than reference drug celecoxib. Molecular modeling studies indicated that the azido substituent can be inserted deeply into the secondary pocket of COX-2 active site for interactions with Arg(513). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.094

文献信息

• Design, synthesis, and biological evaluation of ketoprofen analogs as potent cyclooxygenase-2 inhibitors
  作者：Afshin Zarghi、Razieh Ghodsi

  DOI：10.1016/j.bmc.2010.06.094

  日期：2010.8

  A new series of ketoprofen analogs were synthesized to evaluate their biological activities as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 inhibition studies showed that all compounds were potent and selective inhibitors of the COX-2 isozyme with IC(50) values in the highly potent 0.057-0.085 mu M range, and COX-2 selectivity indexes in the 115 to >1298.7 range. Compounds possessing azido pharmacophore group (8a and 8b) exhibited highly COX-2 inhibitory selectivity and potency even more than reference drug celecoxib. Molecular modeling studies indicated that the azido substituent can be inserted deeply into the secondary pocket of COX-2 active site for interactions with Arg(513). (C) 2010 Elsevier Ltd. All rights reserved.