3-(di-n-butylamino)-7-((2-(diethylamino)ethyl)(ethyl)amino)phenothiazinium iodide | 1241913-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 3-(di-n-butylamino)-7-((2-(diethylamino)ethyl)(ethyl)amino)phenothiazinium iodide
• 英文别名: 3-(Dibutylamino)-7-((2-(diethylamino)ethyl)(ethyl)amino)phenothiazin-5-ium iodide；dibutyl-[7-[2-(diethylamino)ethyl-ethylamino]phenothiazin-3-ylidene]azanium;iodide
• CAS: 1241913-70-1
• 化学式: C₂₈H₄₃N₄S*I
• 分子量: 594.647
• InChiKey: ORWOYRMPOJRVTD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吩噻嗪 在 碘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-(di-n-butylamino)-7-((2-(diethylamino)ethyl)(ethyl)amino)phenothiazinium iodide
  参考文献：
  名称：

  Phenothiazinium photoantimicrobials with basic side chains

  摘要：

  Derivatives of the standard cationic photosensitiser, methylene blue, were synthesised, having extra amino (basic) functionality in the auxochromic side-chain. The resulting analogues were profiled for photodynamic activity in vitro, and screened against standard Gram-positive and Gram-negative bacteria for photobactericidal activity. The substitution pattern of the derivatives was such that ionisation of the amino groups in situ, via protonation, provided a range of charge distribution and degree of charge across the molecular framework.While most examples exhibited greater activity than the lead compound, in addition to similar activity to the known, but more powerful, phenothiazinium photoantimicrobial, dimethyl methylene blue, this was also associated with relatively high dark toxicity, inferring that these compounds were targeting crucial structures before illumination.One derivative having an asymmetrical structure, with separation between a lipophilic and a hydrophilic region exhibited a combination of very high phototoxicity coupled with very low dark effects, against both the standard screen and an additional one containing further, relevant pathogen species, including Candida albicans. It is suggested that the great activity of this analogue is due to efficient membrane targeting. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2014.12.017

文献信息

• Phenothiazinium photoantimicrobials with basic side chains
  作者：Mark Wainwright、Joanna Antczak、Martyna Baca、Ciara Loughran、Katie Meegan

  DOI：10.1016/j.jphotobiol.2014.12.017

  日期：2015.9

  Derivatives of the standard cationic photosensitiser, methylene blue, were synthesised, having extra amino (basic) functionality in the auxochromic side-chain. The resulting analogues were profiled for photodynamic activity in vitro, and screened against standard Gram-positive and Gram-negative bacteria for photobactericidal activity. The substitution pattern of the derivatives was such that ionisation of the amino groups in situ, via protonation, provided a range of charge distribution and degree of charge across the molecular framework.While most examples exhibited greater activity than the lead compound, in addition to similar activity to the known, but more powerful, phenothiazinium photoantimicrobial, dimethyl methylene blue, this was also associated with relatively high dark toxicity, inferring that these compounds were targeting crucial structures before illumination.One derivative having an asymmetrical structure, with separation between a lipophilic and a hydrophilic region exhibited a combination of very high phototoxicity coupled with very low dark effects, against both the standard screen and an additional one containing further, relevant pathogen species, including Candida albicans. It is suggested that the great activity of this analogue is due to efficient membrane targeting. (C) 2015 Elsevier B.V. All rights reserved.