[(3S)-5-oxooxolan-3-yl] 2-methylcyclopropane-1-carboxylate | 1426843-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: [(3S)-5-oxooxolan-3-yl] 2-methylcyclopropane-1-carboxylate
• CAS: 1426843-33-5
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: BDLJVJSZWKCWIP-HUDPQJTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基环丙羧酸 、 (S)-(-)-β-羟基-γ-丁内酯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(3S)-5-oxooxolan-3-yl] 2-methylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Honaucins A−C, Potent Inhibitors of Inflammation and Bacterial Quorum Sensing: Synthetic Derivatives and Structure-Activity Relationships

  摘要：

  Honaucins A-C were isolated from the cyanobacterium Leptolyngbya crossbyana which was found overgrowing corals on the Hawaiian coast. Honaucin A consists of (S)-3-hydroxy-gamma-butyrolactone and 4-chlorocrotonic acid, which are connected via an ester linkage. Honaucin A and its two natural analogs exhibit potent inhibition of both bioluminescence, a quorum-sensing-dependent phenotype, in Vibrio harveyi BB120 and lipopolysaccharide-stimulated nitric oxide production in the murine macrophage cell line RAW264.7. The decrease in nitric oxide production was accompanied by a decrease in the transcripts of several proinflammatory cytokines, most dramatically interleukin-1 beta. Synthesis of honaucin A, as well as a number of analogs, and subsequent evaluation in anti-inflammation and quorum-sensing inhibition bioassays revealed the essential structural features for activity in this chemical class and provided analogs with greater potency in both assays.

  DOI：

  10.1016/j.chembiol.2012.03.014

文献信息

• ANTI-INFLAMMATORY AND QUORUM SENSING INHIBITION COMPOUNDS AND METHODS OF MAKING AND USING THEM
  申请人：Gerwick William

  公开号：US20140147481A1

  公开（公告）日：2014-05-29

  The invention provides novel compositions based on a structure designated as “Honaucin A”, including Honaucin A variants and analogs, and pharmaceutical compositions, liposomes and nanoparticles comprising them, and methods of making and using them. In one embodiment these Honaucin A compounds, and variants and analogs thereof are used to ameliorate (including to treat or prevent) inflammation. In one embodiment, these Honaucin A compounds, and variants and analogs thereof are used to ameliorate (including to treat or prevent) inflammation. In one embodiment, these Honaucin A compounds, and variants and analogs thereof are used as bacterial quorumsensing inhibitors. Accordingly, in alternative embodiments the compositions of the invention are used as anti-bacterial agents.
• US9073884B2
  申请人：——

  公开号：US9073884B2

  公开（公告）日：2015-07-07