2-(N,N-dimethyl)-N′-hexadecylethanamide | 94678-00-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(N,N-dimethyl)-N′-hexadecylethanamide
• 英文别名: 2-(dimethylamino)-N-hexadecylacetamide
• CAS: 94678-00-9
• 化学式: C₂₀H₄₂N₂O
• 分子量: 326.566
• InChiKey: FXOWCKKUKRPJAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N′-(propane-1,3-diyl) bis(2-bromoethanamide) 、 2-(N,N-dimethyl)-N′-hexadecylethanamide 以 氯仿 为溶剂， 反应 24.0h， 以99%的产率得到N,N′-(propane-1,3-diethanamide) bis(N,N-dimethyl-(N′-hexadecylethanamide)ammonium bromide)
  参考文献：
  名称：

  Membrane Active Small Molecules Show Selective Broad Spectrum Antibacterial Activity with No Detectable Resistance and Eradicate Biofilms

  摘要：

  Treating bacterial biofilms With conventional antibiotics is limited due to ineffectiveness of the drugs and higher propensity to develop bacterial resistance. Development of new classes of antibacterial therapeutics with alternative mechanisms of action has become imperative. Herein, we report the design, synthesis, and biological evaluations of novel membrane,active small molecules featuring two positive charges, four nonpeptidic,amide groups, and variable hydro, phobic/hydrophilic (amphiphilic) character. The biocides synthesized via a facile methodology not only displayed good antibacterial activity against wild-type bacteria but also showed high activity against various drug-resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecium (VRE), and beta-lactam-resistant Klebsiella pneumoniae. Further, these biocides not only inhibited the formation of biofilms but also disrupted the established S. aureus and E. coli biofilms. The membrane-active biocides hindered the propensity to develop bacterial resistance. Moreover; the biocides showed negligible toxicity against mammalian cells and thus bear potential to be used as therapeutic agents.

  DOI：

  10.1021/acs.jmedchem.5b00443
• 作为产物：
  描述：

  十六胺 在 potassium carbonate 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 28.0h， 生成 2-(N,N-dimethyl)-N′-hexadecylethanamide
  参考文献：
  名称：

  Membrane Active Small Molecules Show Selective Broad Spectrum Antibacterial Activity with No Detectable Resistance and Eradicate Biofilms

  摘要：

  Treating bacterial biofilms With conventional antibiotics is limited due to ineffectiveness of the drugs and higher propensity to develop bacterial resistance. Development of new classes of antibacterial therapeutics with alternative mechanisms of action has become imperative. Herein, we report the design, synthesis, and biological evaluations of novel membrane,active small molecules featuring two positive charges, four nonpeptidic,amide groups, and variable hydro, phobic/hydrophilic (amphiphilic) character. The biocides synthesized via a facile methodology not only displayed good antibacterial activity against wild-type bacteria but also showed high activity against various drug-resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecium (VRE), and beta-lactam-resistant Klebsiella pneumoniae. Further, these biocides not only inhibited the formation of biofilms but also disrupted the established S. aureus and E. coli biofilms. The membrane-active biocides hindered the propensity to develop bacterial resistance. Moreover; the biocides showed negligible toxicity against mammalian cells and thus bear potential to be used as therapeutic agents.

  DOI：

  10.1021/acs.jmedchem.5b00443

文献信息

• Composition for External Application to Skin
  申请人：Suzuki Yasuto

  公开号：US20100273875A1

  公开（公告）日：2010-10-28

  A composition for external application to skin, containing a compound represented by formula (I) or a salt thereof, and/or a quaternary ammonium salt represented by formula (II): wherein R 1 is a substituted or unsubstituted, linear or branched chain alkyl group having 2 to 25 carbon atoms; X is —CO—NH—, —O—CO—O—, —NH—CO—, —CO—O—, —O—CO— or —O—; Y is a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms; R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 is an alkyl group having 1 to 4 carbon atoms; R 2 and R 3 are the same as or different from each other; R 4 , R 5 and R 6 , which may the same as or different from each other, each are an alkyl group having 1 to 4 carbon atoms; and A − is a counter ion.

  一种用于外用于皮肤的组合物，含有由式（I）或其盐所代表的化合物和/或由式（II）所代表的季铵盐：其中，R1是具有2到25个碳原子的取代或未取代的线性或支链烷基；X是-CO-NH-，-O-CO-O-，-NH-CO-，-CO-O-，-O-CO-或-O-；Y是具有1到4个碳原子的取代或未取代的亚烷基基团；R2是氢原子或具有1到4个碳原子的烷基基团；R3是具有1到4个碳原子的烷基基团；R2和R3相同或不同；R4、R5和R6，它们可以相同也可以不同，每个都是具有1到4个碳原子的烷基基团；A-是一个反离子。
• DE1139738
  申请人：——

  公开号：——

  公开（公告）日：——
• US9155914B2
  申请人：——

  公开号：US9155914B2

  公开（公告）日：2015-10-13