(S)-4-amino-5-(propylthio)pentanal | 1416310-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-amino-5-(propylthio)pentanal
• CAS: 1416310-83-2
• 化学式: C₈H₁₇NOS
• 分子量: 175.295
• InChiKey: QXYPAAORSMLVHV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  11.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (5S)-N-tert-butoxycarbonyl-5-(propylthiomethyl)pyrrolidin-2-ol 在 三氟乙酸 作用下， 反应 2.0h， 生成 (S)-4-amino-5-(propylthio)pentanal 、 (5S)-5-(propylthiomethyl)pyrrolidin-2-ol
  参考文献：
  名称：

  [EN] 2-METHYLTHIOPYRROLIDINES AND THEIR USE FOR MODULATING BACTERIAL QUORUM SENSING
  [FR] 2-MÉTHYLTHIOPYRROLIDINES ET LEUR UTILISATION POUR MODULER LA DÉTECTION DU QUORUM BACTÉRIEN

  摘要：

  本文披露了化学式（I）的化合物及其在抑制细菌中的群体感应中的应用。

  公开号：

  WO2012174511A1

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.