3-oxo-N-[(3S)-2-oxooxolan-3-yl]non-8-ynamide | 1309794-16-8

• 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: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]non-8-ynamide
• CAS: 1309794-16-8
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: RJDWWGOQNRCQHN-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  6-庚炔酸 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 3-oxo-N-[(3S)-2-oxooxolan-3-yl]non-8-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

• 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.