1-n-octyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione | 1158909-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-n-octyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
• 英文别名: 3-Octylbenzo[f]benzotriazole-4,9-dione
• CAS: 1158909-47-7
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 311.384
• InChiKey: DQLPBFMRVQDRDG-UHFFFAOYSA-N

物化性质

• 沸点：
  493.3±48.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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-n-octyl-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， 生成 1-Ethyl-3-octylbenzo[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：

  1-溴辛烷 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 1-n-octyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
  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

文献信息

• Synthesis and antibacterial activity study of a novel class of cationic anthraquinone analogs
  作者：Jianjun Zhang、Nathan Redman、Anthony Phillip Litke、Jia Zeng、Jixun Zhan、Ka Yee Chan、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2010.11.001

  日期：2011.1

  9-diones has been further investigated. In the process of investigating the factors that control the selectivity and the biological activity associated with these two compounds, a novel class of antibacterial cationic anthraquinone analogs has been developed. Although these compounds are structurally similar, different antibacterial profiles are noted. One lead compound, 4e manifests high potency (MIC < 1 μg/mL)

  我们小组先前曾报道过，使用萘醌，叠氮化钠和烷基卤进行一锅环加成反应可导致形成1-烷基-1 H-和2-烷基-2 H-萘[2,3- d ]三唑- 4,9-二酮。在本文中，离去基团和添加剂对决定1-烷基-1 H-和2-烷基-2 H-萘[2,3- d]形成之间的选择性的影响]三唑-4，9-二酮已被进一步研究。在研究控制与这两种化合物有关的选择性和生物活性的因素的过程中，已开发出一类新型的阳离子阳离子蒽醌类似物。尽管这些化合物在结构上相似，但是注意到了不同的抗菌特性。一种先导化合物4e表现出高效力（MIC <1μg/ mL）和对革兰氏阳性（G +）病原体（包括耐甲氧西林金黄色葡萄球菌（MRSA））的选择性，同时对革兰氏阴性（G-）细菌仅发挥适度的活性。其他铅化合物（4f和4g）具有广泛的抗菌活性，包括MRSA和耐万古霉素粪肠球菌（VRE）可与其他市售阳离子消毒化学品媲美。抗菌特性的这种独特差异可能为新治疗剂的开发铺平道路。
• One-Pot Synthesis of 1- and 2-Substituted Naphtho[2,3-<i>d</i>][1,2,3]triazole-4,9-diones
  作者：Jianjun Zhang、Cheng-Wei Tom Chang

  DOI：10.1021/jo9004926

  日期：2009.6.5

  for the synthesis of 1-alkyl 1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione and 2-alkyl 2H-naphtho[2,3-d][1,2,3]triazole-4,9-dione has been developed. By taking the advantage of difference in basicity, both products can be obtained in good purity. The unique heterocyclic scaffolds of these two products could exert interesting chemical and biological properties. The synthetic protocol is concise and suitable

  一锅三组分[2 + 3]环加成反应，用于合成1-烷基1 H-萘[2,3- d ] [1,2,3]三唑-4,9-二酮和2-烷基2已经开发了H-萘[2,3- d ] [1,2,3]三唑-4,9-二酮。通过利用碱性不同的优点，可以得到纯度高的两种产品。这两种产品独特的杂环支架可以发挥有趣的化学和生物学特性。合成方案简明扼要，适用于按比例放大所需产物的合成。
• 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.