1-decyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione | 1346458-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-decyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
• 英文别名: 3-Decylbenzo[f]benzotriazole-4,9-dione；3-decylbenzo[f]benzotriazole-4,9-dione
• CAS: 1346458-62-5
• 化学式: C₂₀H₂₅N₃O₂
• 分子量: 339.437
• InChiKey: RODIKJCCDQIXKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-decyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione 在 Dowex 1X-8 resin (Cl- form) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 1-Decyl-3-methylbenzo[f]benzotriazol-3-ium-4,9-dione;chloride
  参考文献：
  名称：

  Mode of action investigation for the antibacterial cationic anthraquinone analogs

  摘要：

  Reported previously by our group, we have developed a novel class of antibacterial cationic anthraquinone analogs with superb potency (MIC <1 mu g/mL) against Gram positive (G+) pathogens including Methicillin-resistant Staphylococcus aureus (MRSA). However, most of these compounds only manifest modest antibacterial activity against Gram negative (G-) bacteria. Further investigation on the antibacterial mode of action using fluorogenic dyes reveals that these compounds exert two different modes of action that account for the difference in their antibacterial profile. It was found that most of the compounds exert their antibacterial activity by disrupting the redox processes of bacteria. At high concentration, these compounds can also act as membrane disrupting agents. This information can help to design new therapeutics against various bacteria. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.107
• 作为产物：
  描述：

  萘酚 在 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-decyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
  参考文献：
  名称：

  Metal-free cycloaddition to synthesize naphtho[2,3-d][1,2,3]triazole-4,9-diones

  摘要：

  报道了一种无金属的多米诺[3 + 2]环加成反应，用于构建萘并[2,3-d][1,2,3]三唑-4,9-二酮衍生物，并为叠氮-炔环加成提供了一种替代方法。

  DOI：

  10.1039/c5ob01322d

文献信息

• Synthesis of bioactive 1-alkyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-diones and N-aryl-2-aminomethylene-1,3-indanediones using water as the solvent
  作者：Qian Zhang、Jaya P. Shrestha、Cheng-Wei Tom Chang

  DOI：10.1016/j.tetlet.2014.01.129

  日期：2014.3

  Through a [2+3] cycloaddition reaction, a new environmentally friendly method was developed to enable the synthesis of bioactive 1-alkyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-diones and N-aryl-2-aminomethylene-1,3-indanediones using water as the solvent with good yields and minimum requirement of purification. This new green synthetic protocol is simple and suitable for scale-up synthesis. (C) 2014 Elsevier Ltd. All rights reserved.
• Library Synthesis and Antibacterial Investigation of Cationic Anthraquinone Analogs
  作者：Marina Y. Fosso、Ka Yee Chan、Rylee Gregory、Cheng-Wei Tom Chang

  DOI：10.1021/co2002075

  日期：2012.3.12

  We report the parallel synthesis of a series of novel 4,9-dioxo-4,9-dihydro-1H-naphtho[2-,3-d][1,2,3],triazol-3-ium chloride salts, which are analogs to cationic anthraquinones. Three synthetic protocols were examined leading to a convenient and facile library synthesis of the cationic anthraquinone analogs that contain double alkyl chains of various lengths (C-2-C-12) at N-1 and N-3 positions. The antibacterial activities of these compounds were evaluated against Gram positive bacterium Staphyloccous aureus and Gram negative bacterium Escherichia coli. The antibacterial activities of these compunds were expected to be associated with the structural features of naphthoquinenone, cation and lypophilic alkyl chain and, interestingly, they showed much higher levels of antibacterial activites against G+ than G- bacteria. In addtion, when the total number of carbon atoms of the alkyl groups at both N-1 and N-3 positions lies between 9 and 18, the bactericidal activity against S aureus increased with increasing alkyl chain length at both N-atoms with MIC <= 1 mu g/mL.
• Mode of action investigation for the antibacterial cationic anthraquinone analogs
  作者：Ka Yee Chan、Jianjun Zhang、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmcl.2011.08.107

  日期：2011.11

  Reported previously by our group, we have developed a novel class of antibacterial cationic anthraquinone analogs with superb potency (MIC <1 mu g/mL) against Gram positive (G+) pathogens including Methicillin-resistant Staphylococcus aureus (MRSA). However, most of these compounds only manifest modest antibacterial activity against Gram negative (G-) bacteria. Further investigation on the antibacterial mode of action using fluorogenic dyes reveals that these compounds exert two different modes of action that account for the difference in their antibacterial profile. It was found that most of the compounds exert their antibacterial activity by disrupting the redox processes of bacteria. At high concentration, these compounds can also act as membrane disrupting agents. This information can help to design new therapeutics against various bacteria. (C) 2011 Elsevier Ltd. All rights reserved.
• Metal-free cycloaddition to synthesize naphtho[2,3-d][1,2,3]triazole-4,9-diones
  作者：Ping-Fan Chen、Kung-Kai Kuo、Jaya Kishore Vandavasi、Siva Senthil Kumar Boominathan、Chung-Yu Chen、Jeh-Jeng Wang

  DOI：10.1039/c5ob01322d

  日期：——

  A metal-free domino [3 + 2] cycloaddition is reported to construct naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives and provide an alternative approach to the azide–alkyne cycloadditions.

  报道了一种无金属的多米诺[3 + 2]环加成反应，用于构建萘并[2,3-d][1,2,3]三唑-4,9-二酮衍生物，并为叠氮-炔环加成提供了一种替代方法。