(E)-N-((2,3-dihydro-1H-inden-5-yl)methyl)-N-methyl-3-phenylprop-2-en-1-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-N-((2,3-dihydro-1H-inden-5-yl)methyl)-N-methyl-3-phenylprop-2-en-1-amine
• 英文别名: (E)-N-(2,3-dihydro-1H-inden-5-ylmethyl)-N-methyl-3-phenylprop-2-en-1-amine
• 化学式: C₂₀H₂₃N
• 分子量: 277.409
• InChiKey: AAVTYZWHGZWZCB-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-((2,3-dihydro-1H-inden-5-yl)methyl)-N-methyl-3-phenylprop-2-en-1-amine 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.02h， 生成 (E)-N-((2,3-dihydro-1H-inden-5-yl)methyl)-N-methyl-3-phenylprop-2-en-1-amine hydrochloride
  参考文献：
  名称：

  Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)

  摘要：

  Antivirulence strategies are now attracting interest for the inherent mechanism of action advantages. In our previous work, diapophytoene desaturase (CrtN) was identified to be an attractive and drugable target for fighting pigmented S. aureus infections. In this research, we developed a series of effective benzocycloalkane-derived CrtN inhibitors with submicromolar IC50. Analogue 8 blocked the pigment biosynthesis of three MRSA strains with a nanomolar IC50 value. Corresponding to its mode of action, 8 did not function as a bactericidal agent. 8 could sensitize S. aureus to immune clearance. In vivo, 8 was proven to be efficacious in an S. aureus Newman sepsis model and abscess formation model. For two typical MRSAs,. USA400 MW2 and Mu50, 8 significantly decreased the staphylococcal loads in the liver and kidneys. Moreover, 8 showed minimal antifungal activity compared to that of NTF. In summary, 8 has the potential to be developed as a therapeutic drug, especially against intractable MRSA issues.

  DOI：

  10.1021/acs.jmedchem.6b00122
• 作为产物：
  描述：

  5-羟基甲基茚满 在 三溴化磷 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-N-((2,3-dihydro-1H-inden-5-yl)methyl)-N-methyl-3-phenylprop-2-en-1-amine
  参考文献：
  名称：

  Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)

  摘要：

  Antivirulence strategies are now attracting interest for the inherent mechanism of action advantages. In our previous work, diapophytoene desaturase (CrtN) was identified to be an attractive and drugable target for fighting pigmented S. aureus infections. In this research, we developed a series of effective benzocycloalkane-derived CrtN inhibitors with submicromolar IC50. Analogue 8 blocked the pigment biosynthesis of three MRSA strains with a nanomolar IC50 value. Corresponding to its mode of action, 8 did not function as a bactericidal agent. 8 could sensitize S. aureus to immune clearance. In vivo, 8 was proven to be efficacious in an S. aureus Newman sepsis model and abscess formation model. For two typical MRSAs,. USA400 MW2 and Mu50, 8 significantly decreased the staphylococcal loads in the liver and kidneys. Moreover, 8 showed minimal antifungal activity compared to that of NTF. In summary, 8 has the potential to be developed as a therapeutic drug, especially against intractable MRSA issues.

  DOI：

  10.1021/acs.jmedchem.6b00122

文献信息

• [EN] ALKYLAMINE WITH BENZOALICYCLIC SUBSTITUENT AND APPLICATION THEREOF<br/>[FR] ALKYLAMINE AVEC SUBSTITUANT BENZOALICYCLIQUE ET SON APPLICATION<br/>[ZH] 苯并脂肪环取代烷基胺类化合物及其用途
  申请人：UNIV EAST CHINA SCIENCE & TECH

  公开号：WO2017132912A1

  公开（公告）日：2017-08-10

  本发明提供一种苯并脂肪环取代烷基胺类化合物及其用途，具体地，涉及一种式I所示的化合物、或其药学上可接受的盐及其制备方法，以及其在制备金黄色葡萄球菌金黄色色素合成抑制剂类抗菌药物中的应用 (I).
• Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant <i>S. aureus</i> (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)
  作者：Youxin Wang、Hongxia Di、Feifei Chen、Yong Xu、Qiang Xiao、Xuehai Wang、Hanwen Wei、Yanli Lu、Lingling Zhang、Jin Zhu、Lefu Lan、Jian Li

  DOI：10.1021/acs.jmedchem.6b00122

  日期：2016.5.26

  Antivirulence strategies are now attracting interest for the inherent mechanism of action advantages. In our previous work, diapophytoene desaturase (CrtN) was identified to be an attractive and drugable target for fighting pigmented S. aureus infections. In this research, we developed a series of effective benzocycloalkane-derived CrtN inhibitors with submicromolar IC50. Analogue 8 blocked the pigment biosynthesis of three MRSA strains with a nanomolar IC50 value. Corresponding to its mode of action, 8 did not function as a bactericidal agent. 8 could sensitize S. aureus to immune clearance. In vivo, 8 was proven to be efficacious in an S. aureus Newman sepsis model and abscess formation model. For two typical MRSAs,. USA400 MW2 and Mu50, 8 significantly decreased the staphylococcal loads in the liver and kidneys. Moreover, 8 showed minimal antifungal activity compared to that of NTF. In summary, 8 has the potential to be developed as a therapeutic drug, especially against intractable MRSA issues.