(5S)-5-(hexylthiomethyl)pyrrolidin-2-one | 1339086-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (5S)-5-(hexylthiomethyl)pyrrolidin-2-one
• 英文别名: (5S)-5-(hexylsulfanylmethyl)pyrrolidin-2-one
• CAS: 1339086-28-0
• 化学式: C₁₁H₂₁NOS
• 分子量: 215.36
• InChiKey: VQRIYRYCOMUIJX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (5S)-5-(hexylthiomethyl)pyrrolidin-2-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以94%的产率得到(5S)-N-tert-butoxycarbonyl-5-(hexylthiomethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Substituted lactam and cyclic azahemiacetals modulate Pseudomonas aeruginosa quorum sensing

  摘要：

  Quorum sensing (QS) is a population-dependent signaling process bacteria use to control multiple processes including virulence that is critical for establishing infection. The most common QS signaling molecule used by Gram-negative bacteria are acylhomoserine lactones. The development of non-native acylhomoserine lactone (AHL) ligands has emerged as a promising new strategy to inhibit QS in Gram-negative bacteria. In this work, we have synthesized a set of optically pure gamma-lactams and their reduced cyclic azahemiacetal analogues, bearing the additional alkylthiomethyl substituent, and evaluated their effect on the AHL-dependent Pseudomonas aeruginosa las and rhl QS pathways. The concentration of these ligands and the simple structural modification such as the length of the alkylthio substituent has notable effect on activity. The c-lactam derivatives with nonylthio or dodecylthio chains acted as inhibitors of las signaling with moderate potency. The cyclic azahemiacetal with shorter propylthio or hexylthio substituent was found to strongly inhibit both las and rhl signaling at higher concentrations while the propylthio analogue strongly stimulated the las QS system at lower concentrations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.044
• 作为产物：
  描述：

  1-己硫醇 、 (S)-5-溴甲基-2-吡咯烷酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 以94%的产率得到(5S)-5-(hexylthiomethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Substituted lactam and cyclic azahemiacetals modulate Pseudomonas aeruginosa quorum sensing

  摘要：

  Quorum sensing (QS) is a population-dependent signaling process bacteria use to control multiple processes including virulence that is critical for establishing infection. The most common QS signaling molecule used by Gram-negative bacteria are acylhomoserine lactones. The development of non-native acylhomoserine lactone (AHL) ligands has emerged as a promising new strategy to inhibit QS in Gram-negative bacteria. In this work, we have synthesized a set of optically pure gamma-lactams and their reduced cyclic azahemiacetal analogues, bearing the additional alkylthiomethyl substituent, and evaluated their effect on the AHL-dependent Pseudomonas aeruginosa las and rhl QS pathways. The concentration of these ligands and the simple structural modification such as the length of the alkylthio substituent has notable effect on activity. The c-lactam derivatives with nonylthio or dodecylthio chains acted as inhibitors of las signaling with moderate potency. The cyclic azahemiacetal with shorter propylthio or hexylthio substituent was found to strongly inhibit both las and rhl signaling at higher concentrations while the propylthio analogue strongly stimulated the las QS system at lower concentrations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.044

文献信息

• Substituted lactam and cyclic azahemiacetals modulate Pseudomonas aeruginosa quorum sensing
  作者：Venkata L.A. Malladi、Adam J. Sobczak、Natalie Maricic、Senthil Kumar Murugapiran、Lisa Schneper、John Makemson、Kalai Mathee、Stanislaw F. Wnuk

  DOI：10.1016/j.bmc.2011.07.044

  日期：2011.9

  Quorum sensing (QS) is a population-dependent signaling process bacteria use to control multiple processes including virulence that is critical for establishing infection. The most common QS signaling molecule used by Gram-negative bacteria are acylhomoserine lactones. The development of non-native acylhomoserine lactone (AHL) ligands has emerged as a promising new strategy to inhibit QS in Gram-negative bacteria. In this work, we have synthesized a set of optically pure gamma-lactams and their reduced cyclic azahemiacetal analogues, bearing the additional alkylthiomethyl substituent, and evaluated their effect on the AHL-dependent Pseudomonas aeruginosa las and rhl QS pathways. The concentration of these ligands and the simple structural modification such as the length of the alkylthio substituent has notable effect on activity. The c-lactam derivatives with nonylthio or dodecylthio chains acted as inhibitors of las signaling with moderate potency. The cyclic azahemiacetal with shorter propylthio or hexylthio substituent was found to strongly inhibit both las and rhl signaling at higher concentrations while the propylthio analogue strongly stimulated the las QS system at lower concentrations. (C) 2011 Elsevier Ltd. All rights reserved.