1-(4-nitrophenyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione | 132903-89-0

• 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-nitrophenyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
• 英文别名: 3-(4-Nitrophenyl)benzo[f]benzotriazole-4,9-dione
• CAS: 132903-89-0
• 化学式: C₁₆H₈N₄O₄
• 分子量: 320.264
• InChiKey: MMSMMOXZBZCHLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)-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96%的产率得到3-methyl-1-(4-nitrophenyl)-4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d][1,2,3]triazol-3-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Tuning the biological activity of cationic anthraquinone analogues specifically toward Staphylococcus aureus

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2018.08.018
• 作为产物：
  描述：

  4-nitrobenzenediazonium tetrafluoroborate 在 sodium azide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-(4-nitrophenyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
  参考文献：
  名称：

  Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC₅₀ (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.

  DOI：

  10.1016/j.ejmech.2020.112703

文献信息

• Efficient TMG catalyzed synthesis of 1,2,3-triazoles
  作者：Fereshteh Ahmadi、Zeinab Noroozi Tisseh、Minoo Dabiri、Ayoob Bazgir

  DOI：10.1016/j.crci.2013.05.006

  日期：2013.12

  Résumé A practical and efficient method for the synthesis of 1,2,3-triazoles via the cycloaddition reaction of azides and CH-acids in the presence of 1,1,3,3-tetramethylguanidine (TMG) in ethanol at 30 °C has been reported. The simple experimental procedure, short reaction times, and good yields are the advantages of the present method.

  摘要 一种实用且高效的合成1,2,3-三氮唑的方法，通过叠氮化合物与CH-酸在1,1,3,3-四甲基胍（TMG）存在下于30°C的乙醇中进行环加成反应得以报道。该方法的简单实验步骤、较短的反应时间以及良好的产率是其优势所在。
• DBU catalyzed metal free synthesis of fused 1,2,3-triazoles through [3+2] cycloaddition of aryl azides with activated cyclic C–H acids
  作者：Harjinder Singh、Garima Khanna、Jitender M. Khurana

  DOI：10.1016/j.tetlet.2016.05.082

  日期：2016.7

  DBU catalyzed synthesis of fused 1,2,3-triazoles by [3+2] cycloaddition of aryl azides with activated cyclic C–H acids such as dimedone, cyclohexane-1,3-dione, 5-methylcyclohexane-1,3-dione, and 2-hydroxynaphthalene-1,4-dione in PEG-400 has been reported under heating. The important features of this reaction are high yield products, short reaction times, easy availability of starting materials, and

  DBU通过芳基叠氮化物与活化的环状C–H酸（如二甲酮，环己烷-1,3-二酮，5-甲基环己烷-1,3-二酮）的[3 + 2]环加成反应，催化稠合的1,2,3-三唑的合成据报道，PEG-400中的2-羟基萘-1,4-二酮在加热下。该反应的重要特征是高产率的产物，短的反应时间，容易获得的起始原料以及反应介质和催化剂的可循环性。
• Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero, Journal of the Chemical Society. Perkin transactions I, 1991, # 1, p. 71 - 77
  作者：Benati, Luisa、Montevecchi, P. Carlo、Spagnolo, Piero

  DOI：——

  日期：——