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(5S)-5-(nonylthiomethyl)pyrrolidin-2-one | 1339086-64-4

中文名称
——
中文别名
——
英文名称
(5S)-5-(nonylthiomethyl)pyrrolidin-2-one
英文别名
(5S)-5-(nonylsulfanylmethyl)pyrrolidin-2-one
(5S)-5-(nonylthiomethyl)pyrrolidin-2-one化学式
CAS
1339086-64-4
化学式
C14H27NOS
mdl
——
分子量
257.44
InChiKey
VAMCTUAZBLGJLX-ZDUSSCGKSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.3
  • 重原子数:
    17
  • 可旋转键数:
    10
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.93
  • 拓扑面积:
    54.4
  • 氢给体数:
    1
  • 氢受体数:
    2

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    二碳酸二叔丁酯(5S)-5-(nonylthiomethyl)pyrrolidin-2-one4-二甲氨基吡啶三乙基硼氢化锂 作用下, 以 四氢呋喃二氯甲烷 为溶剂, 反应 48.5h, 生成 (5S)-N-tert-butoxycarbonyl-5-(nonylthiomethyl)pyrrolidin-2-ol
    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-壬硫醇(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98%的产率得到(5S)-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
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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.
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