(3R,4R,5S)-N-(tert-butoxycarbonyl)-3,4-dihydroxy-3,4-O-isopropylidene-5-(nonylthiomethyl)pyrrolidin-2-one | 1339086-49-5

• 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: (3R,4R,5S)-N-(tert-butoxycarbonyl)-3,4-dihydroxy-3,4-O-isopropylidene-5-(nonylthiomethyl)pyrrolidin-2-one
• CAS: 1339086-49-5
• 化学式: C₂₂H₃₉NO₅S
• 分子量: 429.621
• InChiKey: HNKLWXPMMZFWBP-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-N-(tert-butoxycarbonyl)-3,4-dihydroxy-3,4-O-isopropylidene-5-(nonylthiomethyl)pyrrolidin-2-one 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以85%的产率得到(3R,4R,5S)-3,4-dihydroxy-5-(nonylthiomethyl)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：

  (2S,3R,4S)-N-tert-butoxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxypyrrolidine 在 sodium periodate 、 ruthenium(IV) oxide hydrate 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.17h， 生成 (3R,4R,5S)-N-(tert-butoxycarbonyl)-3,4-dihydroxy-3,4-O-isopropylidene-5-(nonylthiomethyl)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