(S)-8-azido-1,2-cyclohexylidenedioxy-3,4-octadione | 1042719-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-8-azido-1,2-cyclohexylidenedioxy-3,4-octadione
• CAS: 1042719-20-9
• 化学式: C₁₄H₂₁N₃O₄
• 分子量: 295.338
• InChiKey: XWWBPIXPRDMFPR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  101.36
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-8-azido-1,2-cyclohexylidenedioxy-3,4-octadione 在 氘代硫酸 作用下， 以 氘代二甲亚砜 、 water-d2 为溶剂， 反应 6.0h， 以36%的产率得到(S)-8-azido-1,2-dihydroxyoctane-3,4-dione
  参考文献：
  名称：

  An Unexpected Switch in the Modulation of AI-2-Based Quorum Sensing Discovered through Synthetic 4,5-Dihydroxy-2,3-pentanedione Analogues

  摘要：

  Quorum sensing (QS) has traditionally referred to a mechanism of communication within a species of bacteria. However, emerging research implicates QS in interspecies communication and competition, and such systems have been proposed in a wide variety of bacteria, The AI-2-based QS system represents the most studied of these proposed interspecies systems, and has been proposed to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the treatment of bacterial infections and the study of unknown AI-2-based QS systems. Toward this end, we have designed and synthesized a panel of 4,5-dihydroxy-2,3-pentanedione/AI-2 analogues and evaluated their effects on the AI-2 QS of various bacteria. The panel of compounds exhibited differential effects in the bacterial cell lines examined, providing a platform for the development of broad-spectrum modulators of AI-2-based QS.

  DOI：

  10.1021/ja802353j
• 作为产物：
  描述：

  (R)-1,2-cyclohexylidenedioxyoct-3-yne-8-azido 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 0.25h， 以36%的产率得到(S)-8-azido-1,2-cyclohexylidenedioxy-3,4-octadione
  参考文献：
  名称：

  An Unexpected Switch in the Modulation of AI-2-Based Quorum Sensing Discovered through Synthetic 4,5-Dihydroxy-2,3-pentanedione Analogues

  摘要：

  Quorum sensing (QS) has traditionally referred to a mechanism of communication within a species of bacteria. However, emerging research implicates QS in interspecies communication and competition, and such systems have been proposed in a wide variety of bacteria, The AI-2-based QS system represents the most studied of these proposed interspecies systems, and has been proposed to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the treatment of bacterial infections and the study of unknown AI-2-based QS systems. Toward this end, we have designed and synthesized a panel of 4,5-dihydroxy-2,3-pentanedione/AI-2 analogues and evaluated their effects on the AI-2 QS of various bacteria. The panel of compounds exhibited differential effects in the bacterial cell lines examined, providing a platform for the development of broad-spectrum modulators of AI-2-based QS.

  DOI：

  10.1021/ja802353j

文献信息

• A Multivalent Probe for AI-2 Quorum-Sensing Receptors
  作者：Amanda L. Garner、Junguk Park、Joseph S. Zakhari、Colin A. Lowery、Anjali Kumari Struss、Daisuke Sawada、Gunnar F. Kaufmann、Kim D. Janda

  DOI：10.1021/ja207556d

  日期：2011.10.12

  Multivalency is a common principle in the recognition of cellular receptors, and multivalent agonists and antagonists have played a major role in understanding mammalian cell receptor biology. The study of bacterial cell receptors using similar approaches, however, has lagged behind. Herein we describe our efforts toward the development of a dendrimer-based multivalent probe for studying AI-2 quorum-sensing receptors. From these studies, we have discovered a chemical probe specific for Lsr-type AI-2 quorum-sensing receptors with the potential for enabling the identification of new bacterial species that utilize AI-2 as a quorum-sensing signaling molecule.