N-(3-methoxyphenyl)-4-propoxybenzamide | 5838-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-methoxyphenyl)-4-propoxybenzamide
• CAS: 5838-23-3
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: UYOQZGZWDKLEMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-methoxyphenyl)-4-propoxybenzamide 在 四氯化锡 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 7-methoxy-2-(4-propoxyphenyl)quinolin-4-ol
  参考文献：
  名称：

  2-Phenylquinoline S. aureus NorA Efflux Pump Inhibitors: Evaluation of the Importance of Methoxy Group Introduction

  摘要：

  Antimicrobial resistance (AMR) represents a hot topic in drug discovery. Besides the identification of new antibiotics, the use of nonantibiotic molecules to block resistance mechanisms is a powerful alternative. Bacterial efflux pumps exert an early step in AMR development by allowing bacteria to grow at subinhibitorial drug concentrations. Thus, efflux pump inhibitors (EPIs) offer a great opportunity to fight AMR Given our experience in developing Staphylococcus aureus NorA EPIs, in this work, starting from the 2-phenylquinoline hit 1, we planned the introduction of methoxy groups on the basis of their presence in known NorA EPIs. Among the 35 different synthesized derivatives, compounds 3b and 7d exhibited the best NorA inhibition activity by restoring at very low concentrations ciprofloxacin MICs against resistant S. aureus strains. Interestingly, both compounds displayed EPI activities at nontoxic concentrations for human cells as well as highlighted promising results by preliminary pharmacokinetic studies.

  DOI：

  10.1021/acs.jmedchem.8b00791
• 作为产物：
  描述：

  4-丙氧基苯甲酰氯 、 间氨基苯甲醚 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到N-(3-methoxyphenyl)-4-propoxybenzamide
  参考文献：
  名称：

  2-Phenylquinoline S. aureus NorA Efflux Pump Inhibitors: Evaluation of the Importance of Methoxy Group Introduction

  摘要：

  Antimicrobial resistance (AMR) represents a hot topic in drug discovery. Besides the identification of new antibiotics, the use of nonantibiotic molecules to block resistance mechanisms is a powerful alternative. Bacterial efflux pumps exert an early step in AMR development by allowing bacteria to grow at subinhibitorial drug concentrations. Thus, efflux pump inhibitors (EPIs) offer a great opportunity to fight AMR Given our experience in developing Staphylococcus aureus NorA EPIs, in this work, starting from the 2-phenylquinoline hit 1, we planned the introduction of methoxy groups on the basis of their presence in known NorA EPIs. Among the 35 different synthesized derivatives, compounds 3b and 7d exhibited the best NorA inhibition activity by restoring at very low concentrations ciprofloxacin MICs against resistant S. aureus strains. Interestingly, both compounds displayed EPI activities at nontoxic concentrations for human cells as well as highlighted promising results by preliminary pharmacokinetic studies.

  DOI：

  10.1021/acs.jmedchem.8b00791

文献信息

• NEW METHOD FOR IDENTIFYING COMPOUNDS USEFUL FOR TREATING AND/OR PREVENTING DISEASES ASSOCIATED WITH BONE LOSS
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2331967B1

  公开（公告）日：2015-11-04
• Compounds for treating and/or preventing diseases associated with bone loss
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE -CNRS-

  公开号：EP2716285B1

  公开（公告）日：2016-04-27
• JP2012500393A
  申请人：——

  公开号：JP2012500393A

  公开（公告）日：2012-01-05
• METHOD FOR IDENTIFYING COMPOUNDS USEFUL FOR TREATING AND/OR PREVENTING DISEASE-ASSOCIATED BONE LOSS
  申请人：Blangy Anne

  公开号：US20110212974A1

  公开（公告）日：2011-09-01

  The present invention concerns a method for identifying a compound which inhibits the activation of RAC GTPase by DOCK5 protein comprising the steps of (i) coexpressing the DOCK5 and the RAC proteins in a cell, wherein said DOCK5 protein induces the conversion of inactive RAC, which inactive RAC is bound to GDP, to active RAC, which active RAC is bound to GTP, (ii) contacting or not said cell with said compound, (iii) determining the conversion of inactive RAC to active RAC in the presence or absence of said compound, and (iv) selecting the compound inhibiting the conversion of inactive RAC to active RAC. Said compound is useful for treating disease-associated bone loss.
• US9091678B2
  申请人：——

  公开号：US9091678B2

  公开（公告）日：2015-07-28