4-[4-(4-Chlorophenyl)-2,5-dioxopyrrol-3-yl]benzenesulfonamide | 1599441-84-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-[4-(4-Chlorophenyl)-2,5-dioxopyrrol-3-yl]benzenesulfonamide
• 英文别名: 4-[4-(4-chlorophenyl)-2,5-dioxopyrrol-3-yl]benzenesulfonamide
• CAS: 1599441-84-5
• 化学式: C₁₆H₁₁ClN₂O₄S
• 分子量: 362.793
• InChiKey: JRSDDATYOWGQMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-Chlorosulfonylphenyl)acetyl chloride 在 氨 、 sodium hydride 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 27.0h， 生成 4-[4-(4-Chlorophenyl)-2,5-dioxopyrrol-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and docking analysis of a novel family of 1-methyl-1H-pyrrole-2,5-diones as highly potent and selective cyclooxygenase-2 (COX-2) inhibitors

  摘要：

  As a continuous research for discovery of new COX-2 inhibitors, we present the simple chemical synthesis, in vitro biological screening, and molecular docking study of 1H-pyrrole-2,5-dione derivatives. New synthetic compounds were evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells as well as the COX-1 and COX-2 inhibitory potency. Among them, compound 9d (MPO-0029) was identified as more potent and selective COX-2 inhibitor [PGE(2) IC50 = 8.7 nM, COX-2 IC50 = 6.0 nM; COX-2 selectivity index (SI) = > 168] than celecoxib. Molecular docking experiments were further performed against COX-2 and COX-1 isozymes to determine their probable binding models. Results of molecular docking studies revealed that compound 9d (MPO-0029) has stronger binding interaction with COX-2 than with COX-1 isozyme, and provided successfully complementary theoretical support for the obtained experimental biological data. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.074

文献信息

• Synthesis, biological evaluation, and docking analysis of a novel family of 1-methyl-1H-pyrrole-2,5-diones as highly potent and selective cyclooxygenase-2 (COX-2) inhibitors
  作者：Kyung Ju Kim、Min Ji Choi、Ji-Sun Shin、Minju Kim、Hye-Eun Choi、Seoung Mook Kang、Jae Ho Jin、Kyung-Tae Lee、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2014.02.074

  日期：2014.4

  As a continuous research for discovery of new COX-2 inhibitors, we present the simple chemical synthesis, in vitro biological screening, and molecular docking study of 1H-pyrrole-2,5-dione derivatives. New synthetic compounds were evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells as well as the COX-1 and COX-2 inhibitory potency. Among them, compound 9d (MPO-0029) was identified as more potent and selective COX-2 inhibitor [PGE(2) IC50 = 8.7 nM, COX-2 IC50 = 6.0 nM; COX-2 selectivity index (SI) = > 168] than celecoxib. Molecular docking experiments were further performed against COX-2 and COX-1 isozymes to determine their probable binding models. Results of molecular docking studies revealed that compound 9d (MPO-0029) has stronger binding interaction with COX-2 than with COX-1 isozyme, and provided successfully complementary theoretical support for the obtained experimental biological data. (c) 2014 Elsevier Ltd. All rights reserved.