5-(3'-hydroxypropylamino)-9-diethylaminobenzo[a]phenothiazinium chloride | 1182337-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-(3'-hydroxypropylamino)-9-diethylaminobenzo[a]phenothiazinium chloride
• CAS: 1182337-29-6
• 化学式: C₂₃H₂₅N₃OS*ClH
• 分子量: 427.998
• InChiKey: CYIKZKILCNPEFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.72
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(3'-hydroxypropylamino)-9-diethylaminobenzo[a]phenothiazinium chloride 、 异氰酸苄酯 在 dibutyltin dilaurate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80.5 %的产率得到
  参考文献：
  名称：

  克服光氧化还原催化中的氧气困境：用于抗菌应用的近红外 (NIR) 光触发过氧亚硝酸盐生成

  摘要：

  尼罗蓝衍生物SNB可同时用作I型光敏剂和近红外光催化剂，通过I型光敏化和耐氧光氧化还原催化同时产生超氧阴离子(O 2 ⋅ − )和一氧化氮(NO) ， 分别。O 2 ⋅ −和 NO的结合导致在 NIR 光照射下产生过氧亚硝酸盐，显示出在抗菌和抗生物膜应用中的巨大前景。

  DOI：

  10.1002/anie.202219153
• 作为产物：
  描述：

  2-amino-5-diethylaminophenylthiosulfuric acid sodium salt 、 3-(naphthalen-1-ylamino)propan-1-ol 在 silver carbonate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 5-(3'-hydroxypropylamino)-9-diethylaminobenzo[a]phenothiazinium chloride
  参考文献：
  名称：

  Antimicrobial Photodynamic Efficacy of Side-chain Functionalized Benzo[a]phenothiazinium Dyes

  摘要：

  Abstract5‐(Ethylamino)‐9‐diethylaminobenzo[a]phenothiazinium chloride (EtNBS) is a photosensitizer (PS) with broad antimicrobial photodynamic activity. The objective of this study was to determine the antimicrobial photodynamic effect of side chain/end group modifications of EtNBS on two representative bacterial Gram‐type‐specific strains. Two EtNBS derivatives were synthesized, each functionalized with a different side‐chain end‐group, alcohol or carboxylic acid. In solution, both exhibited photochemical properties consistent with those of the EtNBS parent molecule. In vitro photodynamic therapy experiments revealed an initial Gram‐type‐specificity with two representative strains; both derivatives were phototoxic to Staphylococcus aureus 29213 but the carboxylic acid derivative was nontoxic to Escherichia coli 25922. This difference in photodynamic efficacy was not due to a difference in the binding of the two molecules to the bacteria as the amount of both derivatives bound by bacteria was identical. Interestingly, the carboxylic acid derivative produced no fluorescence emission when observed in cultures of E. coli via fluorescence microscopy. These early findings suggest that the addition of small functional groups could achieve Gram‐type‐specific phototoxicity through altering the photodynamic activity of PSs and deserve further exploration in a larger number of representative strains of each Gram type.

  DOI：

  10.1111/j.1751-1097.2008.00403.x