ethyl 3-oxo-4-(pentyloxy)butanoate | 1342887-40-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 3-oxo-4-(pentyloxy)butanoate
• 英文别名: Ethyl 3-oxo-4-pentoxybutanoate
• CAS: 1342887-40-4
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: VJPFWVXLUTZJHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对三氟甲基苯胺 、 ethyl 3-oxo-4-(pentyloxy)butanoate 在 对甲苯磺酸 作用下， 以 正己烷 为溶剂， 反应 5.0h， 以48%的产率得到2-(pentyloxymethyl)-6-(trifluoromethyl)quinolin-4(1H)-one
  参考文献：
  名称：

  [EN] PQSR MODULATORS
  [FR] MODULATEURS DU PQSR

  摘要：

  本发明涉及一般式（I）的化合物；含有一种或多种化合物的制药组合物；以及将该化合物用作抗感染剂的用途。

  公开号：

  WO2015149821A1
• 作为产物：
  描述：

  戊醇 、 4-氯乙酰乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以90%的产率得到ethyl 3-oxo-4-(pentyloxy)butanoate
  参考文献：
  名称：

  Optimization of anti-virulence PqsR antagonists regarding aqueous solubility and biological properties resulting in new insights in structure–activity relationships

  摘要：

  Increasing antibiotic resistance urgently requires novel therapeutic options to combat bacterial infections. The anti-virulence therapy selectively intervening with pathogenicity without affecting bacterial viability is such a strategy to overcome resistance. We consider the virulence regulator PqsR as an attractive target in the human pathogen Pseudomonas aeruginosa, and recently discovered the first PqsR antagonists, which, however, suffered from poor aqueous solubility. In this work, the antagonists were structurally modified to become more soluble, and their structure-activity as well as structure-property relationships were studied. A novel promising compound with improved solubility and enhanced antivirulence activity was discovered (IC50: 3.8 mu M, pyocyanin). Our findings emphasize the crucial role of substituents at the 3-position and the carbonyl group at the 4-position for ligand receptor interactions, and illuminate the way for further optimization of PqsR antagonists as anti-virulence agents. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.016

文献信息

• PQSR modulators
  申请人：HELMHOLTZ-ZENTRUM FÜR INFEKTIONSFORSCHUNG GMBH

  公开号：US10472326B2

  公开（公告）日：2019-11-12

  The present invention relates to compounds according to general formula (I); to pharmaceutical compositions comprising one or more of the compound(s); and to the use of the compound(s) as anti-infectives.

  本发明涉及符合通式（I）的化合物；含有一种或多种该化合物的药物组合物；以及该化合物作为抗感染药的用途。
• PQSR MODULATORS
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP3126333B1

  公开（公告）日：2018-08-01
• Optimization of anti-virulence PqsR antagonists regarding aqueous solubility and biological properties resulting in new insights in structure–activity relationships
  作者：Cenbin Lu、Benjamin Kirsch、Christine K. Maurer、Johannes C. de Jong、Andrea Braunshausen、Anke Steinbach、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2014.04.016

  日期：2014.5

  Increasing antibiotic resistance urgently requires novel therapeutic options to combat bacterial infections. The anti-virulence therapy selectively intervening with pathogenicity without affecting bacterial viability is such a strategy to overcome resistance. We consider the virulence regulator PqsR as an attractive target in the human pathogen Pseudomonas aeruginosa, and recently discovered the first PqsR antagonists, which, however, suffered from poor aqueous solubility. In this work, the antagonists were structurally modified to become more soluble, and their structure-activity as well as structure-property relationships were studied. A novel promising compound with improved solubility and enhanced antivirulence activity was discovered (IC50: 3.8 mu M, pyocyanin). Our findings emphasize the crucial role of substituents at the 3-position and the carbonyl group at the 4-position for ligand receptor interactions, and illuminate the way for further optimization of PqsR antagonists as anti-virulence agents. (c) 2014 Elsevier Masson SAS. All rights reserved.
• [EN] PQSR MODULATORS<br/>[FR] MODULATEURS DU PQSR
  申请人：HELMHOLTZ ZENTRUM FÜR INFEKTIONSFORSCHUNG GMBH

  公开号：WO2015149821A1

  公开（公告）日：2015-10-08

  The present invention relates to compounds according to general formula (I); to pharmaceutical compositions comprising one or more of the compound(s); and to the use of the compound(s) as anti-infectives.

  本发明涉及一般式（I）的化合物；含有一种或多种化合物的制药组合物；以及将该化合物用作抗感染剂的用途。