ethyl 4-(3-ethoxyphenyl)-5-(4-methoxybenzoyl)-2-oxo-3,4-dihydro-1H-pyrimidine-6-carboxylate | 1613266-04-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 4-(3-ethoxyphenyl)-5-(4-methoxybenzoyl)-2-oxo-3,4-dihydro-1H-pyrimidine-6-carboxylate
• CAS: 1613266-04-8
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: ZUHVEIUGCQJPDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-乙氧基苯甲醛 、 乙基4-(4-甲氧基苯基)-2,4-二氧代丁酸酯 、 尿素 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 以78%的产率得到ethyl 4-(3-ethoxyphenyl)-5-(4-methoxybenzoyl)-2-oxo-3,4-dihydro-1H-pyrimidine-6-carboxylate
  参考文献：
  名称：

  Exploration of the dihydropyrimidine scaffold for the development of new potential anti-inflammatory agents blocking prostaglandin E2 synthase-1 enzyme (mPGES-1)

  摘要：

  Agents targeting microsomal prostaglandin E2 synthase-1 (mPGES-1) would inhibit only PGE2 production induced by inflammatory stimuli and thus could represent a valuable alternative to non-steroidal anti-inflammatory drugs (NSAIDs) as they should be free from the severe side effects of the classic anti-inflammatory drugs. Although several mPGES-1 inhibitors have been so far identified, none of them is currently in clinical trials, therefore the discovery of new molecular platforms, able to interfere with this interesting target, is urgently required. Here, we report the results of a focused collection of dyhidropyrimidin-2(1H)-one based molecules projected by Virtual Screening computational techniques. The key interactions with the receptor counterpart were introduced as a qualitative filter for the selection of the most promising compounds. The biological data obtained are consistent with the computer-aided suggestions and disclosed two interesting molecules showing in vitro mPGES-1 inhibitory activity in the low μM range.

  DOI：

  10.1016/j.ejmech.2014.04.061

文献信息

• Exploration of the dihydropyrimidine scaffold for the development of new potential anti-inflammatory agents blocking prostaglandin E2 synthase-1 enzyme (mPGES-1)
  作者：Gianluigi Lauro、Maria Strocchia、Stefania Terracciano、Ines Bruno、Katrin Fischer、Carlo Pergola、Oliver Werz、Raffaele Riccio、Giuseppe Bifulco

  DOI：10.1016/j.ejmech.2014.04.061

  日期：2014.6

  Agents targeting microsomal prostaglandin E2 synthase-1 (mPGES-1) would inhibit only PGE2 production induced by inflammatory stimuli and thus could represent a valuable alternative to non-steroidal anti-inflammatory drugs (NSAIDs) as they should be free from the severe side effects of the classic anti-inflammatory drugs. Although several mPGES-1 inhibitors have been so far identified, none of them is currently in clinical trials, therefore the discovery of new molecular platforms, able to interfere with this interesting target, is urgently required. Here, we report the results of a focused collection of dyhidropyrimidin-2(1H)-one based molecules projected by Virtual Screening computational techniques. The key interactions with the receptor counterpart were introduced as a qualitative filter for the selection of the most promising compounds. The biological data obtained are consistent with the computer-aided suggestions and disclosed two interesting molecules showing in vitro mPGES-1 inhibitory activity in the low μM range.