2-hydroxy-N,N-dimethyl-N-((1-oxo-1H-phenalen-2-yl)methyl)ethanaminium chloride | 1612156-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 2-hydroxy-N,N-dimethyl-N-((1-oxo-1H-phenalen-2-yl)methyl)ethanaminium chloride
• 英文别名: 2-Hydroxyethyl-dimethyl-[(1-oxophenalen-2-yl)methyl]azanium;chloride；2-hydroxyethyl-dimethyl-[(1-oxophenalen-2-yl)methyl]azanium;chloride
• CAS: 1612156-66-7
• 化学式: C₁₈H₂₀NO₂*Cl
• 分子量: 317.815
• InChiKey: ARRZMBLVFDFRCQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  萘嵌苯酮 在 盐酸 、 磷酸 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 2-hydroxy-N,N-dimethyl-N-((1-oxo-1H-phenalen-2-yl)methyl)ethanaminium chloride
  参考文献：
  名称：

  Improving Photodynamic Inactivation of Bacteria in Dentistry: Highly Effective and Fast Killing of Oral Key Pathogens with Novel Tooth-Colored Type-II Photosensitizers

  摘要：

  Increasing antibiotic resistances in microorganisms create serious problems in public health. This demands alternative approaches for killing pathogens to supplement standard treatment methods. Photodynamic inactivation of bacteria (PIB) uses light activated photosensitizers (PS) to generate reactive oxygen species immediately upon illumination, inducing lethal phototoxicity. Positively charged phenalen-1-one derivatives are a new generation of PS for light-mediated killing of pathogens with outstanding singlet oxygen quantum yield ΦΔ of >97%. Upon irradiation with a standard photopolymerizer light (bluephase C8, 1260 ± 50 mW/cm(2)) the PS showed high activity against the oral key pathogens Enterococcus faecalis, Actinomyces naeslundii, Streptococcus mutans, and Aggregatibacter actinomycetemcomitans. At a concentration of 10 μM, a maximum efficacy of more than 6 log10 steps (≥ 99.9999%) of bacteria killing is reached in less than 1 min (light dose 50 J/cm(2)) after one single treatment. The pyridinium substituent as positively charged moiety is especially advantageous for antimicrobial action.

  DOI：

  10.1021/jm4019492

文献信息

• Improving Photodynamic Inactivation of Bacteria in Dentistry: Highly Effective and Fast Killing of Oral Key Pathogens with Novel Tooth-Colored Type-II Photosensitizers
  作者：Andreas Späth、Christoph Leibl、Fabian Cieplik、Karin Lehner、Johannes Regensburger、Karl-Anton Hiller、Wolfgang Bäumler、Gottfried Schmalz、Tim Maisch

  DOI：10.1021/jm4019492

  日期：2014.6.26

  Increasing antibiotic resistances in microorganisms create serious problems in public health. This demands alternative approaches for killing pathogens to supplement standard treatment methods. Photodynamic inactivation of bacteria (PIB) uses light activated photosensitizers (PS) to generate reactive oxygen species immediately upon illumination, inducing lethal phototoxicity. Positively charged phenalen-1-one derivatives are a new generation of PS for light-mediated killing of pathogens with outstanding singlet oxygen quantum yield ΦΔ of >97%. Upon irradiation with a standard photopolymerizer light (bluephase C8, 1260 ± 50 mW/cm(2)) the PS showed high activity against the oral key pathogens Enterococcus faecalis, Actinomyces naeslundii, Streptococcus mutans, and Aggregatibacter actinomycetemcomitans. At a concentration of 10 μM, a maximum efficacy of more than 6 log10 steps (≥ 99.9999%) of bacteria killing is reached in less than 1 min (light dose 50 J/cm(2)) after one single treatment. The pyridinium substituent as positively charged moiety is especially advantageous for antimicrobial action.