3-decanoylltetramic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-decanoylltetramic acid
• 英文别名: 3-(1-Hydroxydecylidene)pyrrolidine-2,4-dione；3-(1-hydroxydecylidene)pyrrolidine-2,4-dione
• 化学式: C₁₄H₂₃NO₃
• 分子量: 253.342
• InChiKey: USWXONDRQANYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-decanoylltetramic acid 、 苯胺 以 甲苯 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  某些3-烯胺四酸的合成，抗菌活性和构效关系研究

  摘要：

  据报道3-烯胺四酸作为抗菌剂的合成与评价。与类似的3-酰基四酸相反，烯胺四酸类化合物对有限范围的生物显示适度的抗菌活性，甚至该活性也强烈依赖于四酸酯环取代基的身份。而且，这些化合物似乎具有与类似的3-酰基四甲酸不同的作用方式，并且似乎为进一步完善药物发现提供了更多有限的机会。

  DOI：

  10.1016/j.bmcl.2014.03.013
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-3-decanoyltetramic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到3-decanoylltetramic acid
  参考文献：
  名称：

  Targeting Staphylococcus aureus Quorum Sensing with Nonpeptidic Small Molecule Inhibitors

  摘要：

  A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.

  DOI：

  10.1021/jm500215s

文献信息

• Targeting <i>Staphylococcus aureus</i> Quorum Sensing with Nonpeptidic Small Molecule Inhibitors
  作者：Ewan J. Murray、Rebecca C. Crowley、Alex Truman、Simon R. Clarke、James A. Cottam、Gopal P. Jadhav、Victoria R. Steele、Paul O’Shea、Catharina Lindholm、Alan Cockayne、Siri Ram Chhabra、Weng C. Chan、Paul Williams

  DOI：10.1021/jm500215s

  日期：2014.3.27

  A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.
• Synthesis, antibiotic activity and structure–activity relationship study of some 3-enaminetetramic acids
  作者：Yong-Chul Jeong、Muhammad Anwar、Mark G. Moloney

  DOI：10.1016/j.bmcl.2014.03.013

  日期：2014.4

  The synthesis and evaluation of 3-enaminetetramic acids as antibacterial agents is reported; contrary to the analogous 3-acyltetramic acids, the enaminetetramic acid class of compound exhibits modest antibacterial activity against a limited spectrum of organisms, and even that activity is strongly dependent on the identity of the tetramate ring substituents. Moreover, these compounds appear to have

  据报道3-烯胺四酸作为抗菌剂的合成与评价。与类似的3-酰基四酸相反，烯胺四酸类化合物对有限范围的生物显示适度的抗菌活性，甚至该活性也强烈依赖于四酸酯环取代基的身份。而且，这些化合物似乎具有与类似的3-酰基四甲酸不同的作用方式，并且似乎为进一步完善药物发现提供了更多有限的机会。