diethyl 1-cyclobutyl-4-(cyclobutylamino)-5-oxo-2, 5-dihydro-1H-pyrrole-2, 3-dicarboxylate | 1404481-70-4

• 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 1-cyclobutyl-4-(cyclobutylamino)-5-oxo-2, 5-dihydro-1H-pyrrole-2, 3-dicarboxylate
• 英文别名: diethyl 1-cyclobutyl-4-(cyclobutylamino)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate；diethyl 1-cyclobutyl-4-(cyclobutylamino)-5-oxo-2H-pyrrole-2,3-dicarboxylate
• CAS: 1404481-70-4
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: PQOKDZYDNQTGKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 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 、 环丁基胺 在 palladium(II) trifluoroacetate 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以34%的产率得到diethyl 1-cyclobutyl-4-(cyclobutylamino)-5-oxo-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 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.