1-(4-methoxyphenyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione | 132903-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methoxyphenyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
• 英文别名: 3-(4-Methoxyphenyl)benzo[f]benzotriazole-4,9-dione
• CAS: 132903-82-3
• 化学式: C₁₇H₁₁N₃O₃
• 分子量: 305.293
• InChiKey: ASDVZFQCQXCJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione 、 三氟甲烷磺酸甲酯 以 甲苯 为溶剂， 以80%的产率得到4,9-dioxo-1-(4-methoxyphenyl)-3-methylnaphtho[2,3-d][1,2,3]triazol-3-ium trifluoromethanesulfonate
  参考文献：
  名称：

  阳离子蒽醌类似物的合成及其抗癌活性关系的研究

  摘要：

  我们合成了一系列新颖的4,9-二氧代-4,9-二氢-1 H-萘[2,3- d ] [1,2,3]三唑-3-鎓盐，可以将其视为类似物阳离子蒽醌。与我们之前报道的类似类似物不同，这些化合物显示出相对较弱的抗菌活性，但发挥了很强的抗癌活性（从低至μM到nM GI 50），尤其是针对黑色素瘤，结肠癌，非小细胞肺癌和中枢神经系统（CNS）癌症的治疗。这些化合物在结构上不同于其前身，因为它们具有直接连接到阳离子蒽醌骨架上的芳基而不是烷基链。对结构-活性关系（SAR）的进一步研究表明，芳环上的给电子取代基在通过共振效应增强抗癌活性方面具有重要作用。这些基团的立体位阻是不利的，但其影响不如共振效应。阳离子蒽醌类似物在N-1位的连接基团的差异是生物活性从抗菌药向抗癌药转换的主要结构因素。

  DOI：

  10.1016/j.ejmech.2014.02.060
• 作为产物：
  描述：

  1-叠氮基-4-甲氧基苯 以 六甲基磷酰三胺 、 苯 为溶剂， 生成 1-(4-methoxyphenyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
  参考文献：
  名称：

  Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero, Journal of the Chemical Society. Perkin transactions I, 1991, # 1, p. 71 - 77

  摘要：

  DOI：

文献信息

• A mode of action study of cationic anthraquinone analogs: a new class of highly potent anticancer agents
  作者：Jaya P. Shrestha、Yagya Prasad Subedi、Liaohai Chen、Cheng-Wei Tom Chang

  DOI：10.1039/c5md00314h

  日期：——

  Previously, we reported the synthesis and structure–activity relationship (SAR) study of a series of novel 4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d][1,2,3]triazol-3-ium salts, which had very potent anti-proliferative activities (low μM to nM GI₅₀) against a broad range of cancer cells.

  之前，我们报告了一系列新型4,9-二氧代-4,9-二氢-1H-萘并[2,3-d][1,2,3]三唑-3-ium盐的合成和结构-活性关系（SAR）研究，这些化合物对广泛范围的癌细胞具有非常强的抗增殖活性（低微摩尔到纳摩尔级的GI50值）。
• 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。
• Tuning the biological activity of cationic anthraquinone analogues specifically toward Staphylococcus aureus
  作者：Yagya Prasad Subedi、Madher N. Alfindee、Jaya P. Shrestha、Cheng-Wei Tom Chang

  DOI：10.1016/j.ejmech.2018.08.018

  日期：2018.9

  Development of new antibacterial agents against drug resistant bacteria is an imminent task, especially against methicillin-resistant Staphylococcus aureus (MRSA). While MRSA can still be treated with broad spectrum antibiotics, the use of which often leads to the disruption of normal microbial flora leading to Clostridium difficile infection (CDI). Herein, a new class of antibacterial agent, cationic anthraquinone analogues specifically against MRSA, has been developed. Through the variation and optimization of substituents, these agents are selective toward MRSA, and not Gram negative bacteria which may avoid the problem of CDI. In addition, newly discovered lead compounds also show significantly reduced cytotoxicity against normal mammalian cells than cancerous cells. This interesting finding can alleviate the toxicity and side effect problems often associate with the use of antibiotics. (C) 2018 Elsevier Masson SAS. All rights reserved.
• 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.