(S)-3-oxo-N-(2-oxotetrahydrofuran-3-yl)tridec-12-ynamide | 1309794-15-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-oxo-N-(2-oxotetrahydrofuran-3-yl)tridec-12-ynamide
• 英文别名: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]tridec-12-ynamide
• CAS: 1309794-15-7
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: AYCGKVOUELNADU-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  10-十一碳炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-3-oxo-N-(2-oxotetrahydrofuran-3-yl)tridec-12-ynamide
  参考文献：
  名称：

  Synthesis of ‘clickable’ acylhomoserine lactone quorum sensing probes: Unanticipated effects on mammalian cell activation

  摘要：

  Alkynyl- and azido-tagged 3-oxo-C-12-acylhomoserine lactone probes have been synthesized to examine their potential utility as probes for discovering the mammalian protein target of the Pseudomonas aeruginosa autoinducer, 3-oxo-C-12-acylhomoserine lactone. Although such substitutions are commonly believed to be quite conservative, from these studies, we have uncovered a drastic difference in activity between the alkynyl- and azido-modified compounds, and provide an example where such structural modification has proved to be much less than conservative. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.122

文献信息

• Quorum sensing modulators exhibit cytotoxicity in Hodgkin’s lymphoma cells and interfere with NF-κB signaling
  作者：Natarajan Nandakumar、Rambabu Dandela、Jacob Gopas、Michael M. Meijler

  DOI：10.1016/j.bmcl.2017.05.012

  日期：2017.7

  In recent years it has become evident that bacteria can modulate signaling pathways in host cells through the secretion of small signaling molecules. We have evaluated the cytotoxic effects and NF-kappa B inhibitory activities of a panel of quorum sensing molecules and their reactive analogs on Hodgkin's lymphoma cells (L428). We found that several molecules inhibited NF-kappa B signaling in a dose dependent manner. Three inhibitors (ITC-12, ITC-Cl and Br-Furanone) showed 50% NF-kappa B inhibition at concentrations less than 10 mM (4.1 mu M, 12.8 mu M and 9.9 mu M, respectively). Furthermore, all three molecules displayed cytotoxic effects against L428 cells with IC50 values of 12.4 mu M, 18.3 mu M and 3.1 mu M respectively after 48 h incubation. They also showed inhibition of A549 adenocarcinoma cell migration at low concentrations 5.6 mu M, 2.6 mu M and 7.9 mu M respectively. Further analysis showed that these molecules significantly decrease the degree of expression of proteins of NF-kappa B subunits p50, p65 and RelB both in cytosolic and nuclear fractions. This confirms that these compounds have the potential to modulate the NF-kappa B pathway by suppressing their subunits and thus exhibit cytotoxicity and inactivation of NF-kappa B signaling in Hodgkin's lymphoma cells. (C) 2017 Published by Elsevier Ltd.
• TRAIL ENHANCERS FOR THE SELECTIVE KILLING OF CANCER CELLS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20160272603A1

  公开（公告）日：2016-09-22

  The invention is directed to methods of inducing apoptosis, arresting cell cycle, or inhibiting cellular proliferation, or any combination thereof, in a tumor cell, by administration of an effective amount of an N-acyl homoserine lactone analog (AHL), optionally in conjunction with a tumor modulating agent such tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) to the patient. Novel bioactive analogs of an N-acyl homoserine lactone are also provided.
• US9604950B2
  申请人：——

  公开号：US9604950B2

  公开（公告）日：2017-03-28
• US9765061B2
  申请人：——

  公开号：US9765061B2

  公开（公告）日：2017-09-19
• Synthesis of ‘clickable’ acylhomoserine lactone quorum sensing probes: Unanticipated effects on mammalian cell activation
  作者：Amanda L. Garner、Jing Yu、Anjali Kumari Struss、Colin A. Lowery、Jie Zhu、Sook Kyung Kim、Junguk Park、Alexander V. Mayorov、Gunnar F. Kaufmann、Vladimir V. Kravchenko、Kim D. Janda

  DOI：10.1016/j.bmcl.2010.11.122

  日期：2011.5

  Alkynyl- and azido-tagged 3-oxo-C-12-acylhomoserine lactone probes have been synthesized to examine their potential utility as probes for discovering the mammalian protein target of the Pseudomonas aeruginosa autoinducer, 3-oxo-C-12-acylhomoserine lactone. Although such substitutions are commonly believed to be quite conservative, from these studies, we have uncovered a drastic difference in activity between the alkynyl- and azido-modified compounds, and provide an example where such structural modification has proved to be much less than conservative. (C) 2010 Elsevier Ltd. All rights reserved.