4,9-dihydro-4,9-dioxo-1-(4-methoxybenzyl)naphtho<2,3-d>-v-triazole | 79707-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,9-dihydro-4,9-dioxo-1-(4-methoxybenzyl)naphtho<2,3-d>-v-triazole
• 英文别名: 1-[(4-methoxyphenyl)methyl]-1H,4H,9H-naphtho[2,3-d][1,2,3]triazole-4,9-dione；1-(4-methoxybenzyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione；3-[(4-Methoxyphenyl)methyl]benzo[f]benzotriazole-4,9-dione
• CAS: 79707-02-1
• 化学式: C₁₈H₁₃N₃O₃
• 分子量: 319.32
• InChiKey: VAFYEFQMTCTPOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  4,9-dihydro-4,9-dioxo-1-(4-methoxybenzyl)naphtho<2,3-d>-v-triazole 在 硫酸 、 硝酸 、 三氟乙酸 作用下， 反应 7.17h， 生成 6-nitro-4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]-v-triazole
  参考文献：
  名称：

  Studies on v-triazoles. 9. Antiallergic 4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]-v-triazoles

  摘要：

  A short series of the title compounds was prepared and evaluated for antiallergic activity in the rat passive cutaneous anaphylaxis screen. All but the two N-methylated derivatives were active in this screen by the intravenous route, the most potent being the symmetrical dimethyl compound, 4,9-dihydro-6,7-dimethyl-4,9-dioxo-1H-naphtho[2,3-d]-v-triazole, and its 5-nitro derivative. The latter two compounds were noticeably more potent than disodium cromoglycate, and one of these, the unnitrated material, was selected for further evaluation as a potential antiasthmatic drug.

  DOI：

  10.1021/jm00359a016
• 作为产物：
  描述：

  4-甲氧基氯苄 在 sodium azide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4,9-dihydro-4,9-dioxo-1-(4-methoxybenzyl)naphtho<2,3-d>-v-triazole
  参考文献：
  名称：

  1,3-二甲基-1,2,3-三唑鎓盐的合成安全简便途径及其抗癌活性的研究

  摘要：

  我们已经开发出一种新的安全简便的路线来合成1,3-二甲基-1,2,3-三唑鎓衍生物。我们已经报道了由1-甲基-1 H-萘[2 ]的甲基化合成4,9-dioxo-1,3-二甲基萘[2,3- d ] [1,2,3]三唑-3-氯化铵的合成。，3- d ] [1,2,3]三唑-4,9-二酮。1-甲基-1 H-萘[2,3- d ] [1,2,3]三唑-4,9-二酮的合成效率低下，因为形成了大量副产物，难以分离和分离。同样不安全，因为它需要使用危险的甲基叠氮化物作为起始原料。然而，重要的是开发一种改进的方法来合成4,9-dioxo-1,3-二甲基萘[2,3- d] [1,2,3]三唑-3-盐由于其显着的抗癌活性。本文中，我们报告了该化合物合成的安全便捷途径，这导致了其深层抗癌活性的更详细探索。改进的方法可适用于合成其他感兴趣的1,3-二甲基-1,2,3-三唑鎓盐，而无需使用潜在的爆炸性甲基叠氮化物。用

  DOI：

  10.1016/j.bmcl.2013.08.078

文献信息

• Cerium(III) triflate–catalyzed cycloaddition reaction in aqueous conditions to substituted naphthotriazolediones
  作者：Ya‐Syuan Li、Chien‐Fu Liang

  DOI：10.1002/jccs.202200018

  日期：2022.5

  In this study, the cerium(III) trifluoromethanesulfonate–catalyzed cycloaddition of 1,4-naphthoquinone with functionalized azides in aqueous solutions was used to synthesize naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives. Moreover, our method boasts scalability and completes the synthesis of two key biological compounds. Our method's advantages are environmentally friendly reaction conditions

  本研究采用三氟甲磺酸铈（III）催化的 1,4-萘醌与官能化叠氮化物在水溶液中的环加成反应合成萘并[2,3 - d ][1,2,3]三唑-4,9-二酮衍生物。此外，我们的方法具有可扩展性并完成了两种关键生物化合物的合成。我们的方法的优点是环境友好的反应条件，易于大规模操作，高产率生产的结构多样的产品，以及催化剂的可回收性。
• 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.
• Fluorescent 1,4-Naphthoquinones To Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains
  作者：Naewoo Neo Shin、Hanna Jeon、Youngeun Jung、Seungyeop Baek、Sejin Lee、Hee Chan Yoo、Gi Hun Bae、Keunwan Park、Seung-Hoon Yang、Jung Min Han、Ikyon Kim、YoungSoo Kim

  DOI：10.1021/acschemneuro.9b00093

  日期：2019.6.19

  Recent clinical approvals of brain imaging radiotracers targeting amyloid-beta provided clinicians the tools to detect and confirm Alzheimer's disease pathology without autopsy or biopsy. While current imaging agents are effective in postsymptomatic Alzheimer's patients, there is much room for improvement in earlier diagnosis, hence prompting a need for new and improved amyloid imaging agents. Here we synthesized 41 novel 1,4-naphthoquinone derivatives and initially discovered 14 antiamyloidogenic compounds via in vitro amyloid-beta aggregation assay; however, qualitative analyses of these compounds produced conflicting results and required further investigation. Follow-up docking and biophysical studies revealed that four of these compounds penetrate the blood-brain barrier, directly bind to amyloid-beta aggregates, and enhance fluorescence properties upon interaction. These compounds specifically stain both diffuse and dense-core amyloid-beta plaques in brain sections of APP/PS1 double transgenic Alzheimer's mouse models. Our findings suggest 1,4-naphthoquinones as a new scaffold for amyloid-beta imaging agents for early stage Alzheimer's.
• BUCKLE, D. R.;SMITH, H.;SPICER, B. A.;TEDDER, J. M., J. MED. CHEM., 1983, 26, N 5, 714-719
  作者：BUCKLE, D. R.、SMITH, H.、SPICER, B. A.、TEDDER, J. M.

  DOI：——

  日期：——
• Naphthotriazole derivatives, process for their preparation,intermediates and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0039552B1

  公开（公告）日：1983-09-21