3-di-n-propylaminophenothiazinium triiodide | 854278-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-di-n-propylaminophenothiazinium triiodide
• CAS: 854278-47-0
• 化学式: C₁₈H₂₁N₂S*I₃
• 分子量: 678.158
• InChiKey: JJJZIYQKKGCNJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  16.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-di-n-propylaminophenothiazinium triiodide 、 3,3′-亚氨基双(N,N-二甲基丙胺) 以 甲醇 为溶剂， 以33%的产率得到3-(bis(3-(dimethylamino)propyl)amino)-7-(di-n-propylamino)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
• 作为产物：
  描述：

  吩噻嗪 在 碘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-di-n-propylaminophenothiazinium triiodide
  参考文献：
  名称：

  Phenothiazinium–fluoroquinolone drug conjugates

  摘要：

  Synthesis and antibacterial screening of a homologous series of 3-dialkylaminophenothiazinium-7-norfloxacin conjugates was carried out alongside a corresponding series of symmetrical methylene blue derivatives. The norfloxacin conjugates maintained typical methylene blue derivative photoproperties, such as long wavelength absorption, but produced no measurable singlet oxygen in the standard assay and provided no significant increase in the magnitude of photoantibacterial action, this being similar to the methylene blue homologues, although both the conjugates and homologues were considerably more active than methylene blue itself both against Staphylococcus aureus and Escherichia coli. DNA binding via intercalation was considerably greater for the series of norfloxacin conjugates than for the methylene blue homologues. (C) 2009 Elsevier B. V. and the International Society of Chemotherapy. All rights reserved.

  DOI：

  10.1016/j.ijantimicag.2009.11.022

文献信息

• Phenothiazinium photosensitisers VII: Novel substituted asymmetric N-benzylphenothiaziniums as photoantimicrobial agents
  作者：Mark Wainwright、Simon D. Brandt、Andrew Smith、Andrew Styles、Katie Meegan、Ciara Loughran

  DOI：10.1016/j.jphotobiol.2010.02.008

  日期：2010.5

  The synthesis of asymmetrical analogues of methylene blue, in which one of the dimethylamino groups is replaced by a diethylamino or di-n-propylamino group, and the other by benzylamino or 4-substituted benzylamino, is reported, the substituents being alkyl, alkoxyl or halogen. As expected, because of their longer alkyl chains these diethylamino- and di-n-propylamino derivatives proved to be considerably

  据报道，合成了亚甲基蓝的不对称类似物，其中一个二甲基氨基被一个二乙基氨基或二正丙基氨基取代，另一个被苄基氨基或4-取代的苄基氨基取代，取代基是烷基，烷氧基或卤素。如所预期的，由于它们的更长的烷基链，因此这些二乙基氨基和二正丙基氨基衍生物被证明比母体化合物亚甲基蓝具有更高的亲脂性，同时保持了适用于光抗菌剂的最大吸收波长和单线态氧效率。 同样如预期的那样，在针对革兰氏阳性和革兰氏阴性细菌的筛选测试中，取代的苄基氨基衍生物在光照下具有很高的活性，可能是由于单线态氧损伤，并且相对于标准品亚甲基蓝显示出对两种类别的活性大大提高。此外，亲脂性更高的衍生物对大肠杆菌表现出更大的活性。这可能是由于与该革兰氏阴性细菌的富含脂质的外膜的相互作用增加。相对于亚甲蓝，衍生物的DNA结合也增加了，在强嵌入剂的典型结合下显示出大的红移（> 10 nm）。