(5Z)-5-[[4-(diethylamino)phenyl]methylidene]-3-[2-hydroxy-3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]imidazolidine-2,4-dione | 1416719-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5Z)-5-[[4-(diethylamino)phenyl]methylidene]-3-[2-hydroxy-3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]imidazolidine-2,4-dione
• CAS: 1416719-69-1
• 化学式: C₂₃H₃₅N₅O₄
• 分子量: 445.562
• InChiKey: PLPVWKOMEUUEBG-QNGOZBTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  99.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 在 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (5Z)-5-[[4-(diethylamino)phenyl]methylidene]-3-[2-hydroxy-3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]imidazolidine-2,4-dione
  参考文献：
  名称：

  Search for new tools to combat Gram-negative resistant bacteria among amine derivatives of 5-arylidenehydantoin

  摘要：

  A series of amine-alkyl derivatives of 5-arylidenehydantoin 3-21 was evaluated for their ability to improve antibiotic effectiveness in two strains of Gram-negative Enterobacter aerogenes: the reference strain (ATCC-13048) and the chloramphenicol-resistant derivative over-producing the AcrAB-TolC efflux pump (CM-64). Three antibiotics, chloramphenicol, nalidixic acid and sparfloxacin were used as markers of efflux pump activity. New compounds (5-16) were obtained within 3-4 step synthesis using Knoevenagel condensation, Mitsunobu reaction and microwave aided N-alkylation. Molecular modeling based structure-activity relationship (SAR) studies were performed. The most active compounds: (Z)-5-(4-(diethylamino) benzylidene)-3-(2-hydroxy-3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)imidazolidine-2,4-dione (14) and (Z)-5-(2,4-dimethoxybenzylidene)-3-(2-hydroxy-3-(isopropylamino)propyl)imidazolidine-2,4-dione (15) induced fourfold decrease of minimal inhibition concentration (MIC) of all tested antibiotics in the strain CM-64 overexpressing the AcrAB-TolC pump. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.053

文献信息

• Search for new tools to combat Gram-negative resistant bacteria among amine derivatives of 5-arylidenehydantoin
  作者：Jadwiga Handzlik、Ewa Szymańska、Sandrine Alibert、Jacqueline Chevalier、Ewa Otrębska、Elżbieta Pękala、Jean-Marie Pagès、Katarzyna Kieć-Kononowicz

  DOI：10.1016/j.bmc.2012.10.053

  日期：2013.1

  A series of amine-alkyl derivatives of 5-arylidenehydantoin 3-21 was evaluated for their ability to improve antibiotic effectiveness in two strains of Gram-negative Enterobacter aerogenes: the reference strain (ATCC-13048) and the chloramphenicol-resistant derivative over-producing the AcrAB-TolC efflux pump (CM-64). Three antibiotics, chloramphenicol, nalidixic acid and sparfloxacin were used as markers of efflux pump activity. New compounds (5-16) were obtained within 3-4 step synthesis using Knoevenagel condensation, Mitsunobu reaction and microwave aided N-alkylation. Molecular modeling based structure-activity relationship (SAR) studies were performed. The most active compounds: (Z)-5-(4-(diethylamino) benzylidene)-3-(2-hydroxy-3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)imidazolidine-2,4-dione (14) and (Z)-5-(2,4-dimethoxybenzylidene)-3-(2-hydroxy-3-(isopropylamino)propyl)imidazolidine-2,4-dione (15) induced fourfold decrease of minimal inhibition concentration (MIC) of all tested antibiotics in the strain CM-64 overexpressing the AcrAB-TolC pump. (C) 2012 Elsevier Ltd. All rights reserved.