diethyl 5-oxo-1-(p-tolyl)-4-(p-tolylamino)-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate | 1404481-53-3

• 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: diethyl 5-oxo-1-(p-tolyl)-4-(p-tolylamino)-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate
• 英文别名: diethyl 4-(4-methylanilino)-1-(4-methylphenyl)-5-oxo-2H-pyrrole-2,3-dicarboxylate
• CAS: 1404481-53-3
• 化学式: C₂₄H₂₆N₂O₅
• 分子量: 422.481
• InChiKey: ZPPSARSJZRFVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙醛酸乙酯 、 乙烷,三氯氟- 在 palladium(II) trifluoroacetate 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以62%的产率得到diethyl 5-oxo-1-(p-tolyl)-4-(p-tolylamino)-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate
  参考文献：
  名称：

  乙二醛乙二醛和胺的钯催化串联环化：高度取代的环状脱氢-α-氨基酸衍生物的快速组装

  摘要：

  在Pd（TFA）2（5 mol％）存在下进行乙二醛酸乙酯和胺的新型级联环化反应，得到环状脱氢-α-氨基酸衍生物。该方法以高收率快速简便地获得高度取代的二氢吡咯-2-酮。

  DOI：

  10.1021/ol302483f

文献信息

• Pd-Catalyzed Tandem Cyclization of Ethyl Glyoxalate and Amines: Rapid Assembly of Highly Substituted Cyclic Dehydro-α-Amino Acid Derivatives
  作者：Yueting Luo、Xiaoxia Lu、Yong Ye、Ya Guo、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/ol302483f

  日期：2012.11.16

  A novel cascade cyclization of ethyl glyoxalate and amines proceeds in the presence of Pd(TFA)2 (5 mol %) to give the cyclic dehydro-α-amino acid derivatives. This method provides a fast and simple access to highly substituted dihydro-pyrrol-2-ones in good yields.

  在Pd（TFA）2（5 mol％）存在下进行乙二醛酸乙酯和胺的新型级联环化反应，得到环状脱氢-α-氨基酸衍生物。该方法以高收率快速简便地获得高度取代的二氢吡咯-2-酮。
• Synthesis of functionalized 2-pyrrolidinones via domino reactions of arylamines, ethyl glyoxylate and acetylenedicarboxylates
  作者：Hong Gao、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.tet.2012.11.018

  日期：2013.1

  successfully developed via the domino reactions of ethyl glyoxylate and acetylenedicarboxylate with 2 M arylamines in the presence of benzoic acid as catalyst. When two kinds of amines were used in the reaction, the stronger nucleophilic aliphatic amine preferentially added to acetylenedicarboxylate to form the reactive intermediate β-enamino ester and the reaction showed high regioselectivity.

  在乙二酸为催化剂的条件下，通过乙醛酸乙酯和乙炔二羧酸酯与2 M芳胺的多米诺反应，成功开发了一种有效且实用的官能化2-吡咯烷酮合成方法。当在反应中使用两种胺时，优先将更强的亲核脂肪族胺添加到乙炔二羧酸酯中，形成反应性中间体β-烯胺酯，该反应具有较高的区域选择性。
• Synthesis and anti-biofilm activities of dihydro-pyrrol-2-one derivatives on Pseudomonas aeruginosa
  作者：Yong Ye、Fei Fang、Yue Li

  DOI：10.1016/j.bmcl.2014.12.010

  日期：2015.2

  Biofilm formation is an important reason for bacterial resistance to antimicrobials. Many compounds with dihydro-pyrrol-2-one (DPO) have antibacterial effects. It is prospective to base on DPO skeleton to design new compounds for biofilm inhibition. DPO was designed by a novel method of tandem cyclization between ethyl glyoxalate and amines, the series of DPO derivatives were synthesized by change of the amines. Their activities were evaluated by the inhibition of biofilm in Pseudomonas aeruginosa. The interaction of DPO derivatives with mannitol dehydrogenase (MDH) or extracellular DNA (eDNA) in the biofilm was simulated by molecular docking to reveal possible mechanism. 19 new DPO derivatives were synthesized and identified, 15 of them had antibacterial activities, but only 5 of them had more than 50% inhibition on biofilm of P. aeruginosa at 50 mu g/mL. The MDH activity and eDNA content in biofilm decreased significantly after treatment of the DPO derivatives in concentration dependence. The simulation reveals that strong interaction exists between the five DPO derivatives and MDH or eDNA, which are involved in anti-biofilm mechanism. The synthetic method of DPO derivatives is practical to provide effective anti-biofilm agents for P. aeruginosa, and they take effect through inhibition on MDH and eDNA of biofilm. (C) 2014 Elsevier Ltd. All rights reserved.