2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-nitrophenyl)ethanone | 163729-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-nitrophenyl)ethanone
• 英文别名: 2-(Benzotriazol-1-yl)-1-(4-nitrophenyl)ethanone
• CAS: 163729-30-4
• 化学式: C₁₄H₁₀N₄O₃
• mdl: MFCD00589574
• 分子量: 282.258
• InChiKey: XJLCWAVWERRVAR-UHFFFAOYSA-N

物化性质

• 沸点：
  520.7±30.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-nitrophenyl)ethanone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 1-(2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-nitrophenyl)ethylidene)-2-(4-(4-bromophenyl)thiazol-2-yl)hydrazine
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel thiazole substituted benzotriazole derivatives

  摘要：

  A series of novel hybrid molecules 4a-y containing thiazole and benzotriazole templates were designed and synthesized. The structures of the synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR and mass spectral data. All the synthesized compounds were tested for their antimicrobial activity (zone of inhibition) against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. After that minimum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and minimum fungicidal concentrations (MFCs) of all the synthesized compounds were determined. The investigation of antimicrobial screening data revealed that most of the tested compounds showed moderate to good microbial inhibitions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.094
• 作为产物：
  描述：

  T406石油添加剂 、 2-溴-4'-硝基苯乙酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-nitrophenyl)ethanone
  参考文献：
  名称：

  新型苯并三唑基双席夫碱衍生物的合成、体外α-葡萄糖苷酶抑制活性和分子对接研究。

  摘要：

  本研究旨在合成基于苯并三唑的双席夫碱支架 (1-20)，并在体外评估它们的 α-葡萄糖苷酶抑制潜力。发现所有基于苯并三唑基双席夫碱支架的合成类似物在筛选 α-葡萄糖苷酶时都显示出出色的抑制作用。与作为标准药物的阿卡波糖（IC50 = 10.30 ± 0.20 µM）相比，合成支架显示出不同范围的抑制曲线，IC50 值从 1.10 ± 0.05 µM 到 28.30 ± 0.60 µM 不等。在该系列中，十五个支架 1-3、5、6、9-16、18-20 被确定比标准阿卡波糖更有效，而其余五个支架 4、7、8、16 和 17 也显示出效力抗α-葡萄糖苷酶，但发现其效力低于标准阿卡波糖。所有新合成的支架的结构都使用不同的光谱技术（如 HREI-MS 和 1H-和 13C-NMR 光谱）进行了确认。为了找到结构-活性关系，进行了分子对接研究以了解活性抑制剂与酶活性位点的结合模式，结果支持实验数据。

  DOI：

  10.3390/ph16010017

文献信息

• Novel inhibitors of nitric oxide synthase with antioxidant properties
  作者：Loredana Salerno、Maria N. Modica、Giuseppe Romeo、Valeria Pittalà、Maria A. Siracusa、Maria E. Amato、Rosaria Acquaviva、Claudia Di Giacomo、Valeria Sorrenti

  DOI：10.1016/j.ejmech.2012.01.002

  日期：2012.3

  We previously described a series of imidazole-based inhibitors substituted at N-1 with an arylethanone chain as interesting inhibitors of neuronal nitric oxide synthase (nNOS), endowed with good selectivity vs endothelial nitric oxide synthase (eNOS). As a follow up of these studies, several analogs characterized by the presence of substituted imidazoles or other mono or bicyclic nitrogen-containing heterocycles instead of simple imidazole were synthesized, and their biological evaluation as in vitro inhibitors of both nNOS and eNOS is described herein. Most of these compounds showed improved nNOS and eNOS inhibitory activity with respect to reference inhibitors. Selected compounds were also tested to analyze their antioxidant properties. Some of them displayed good capacity to scavenge free radicals and ability to reduce lipid peroxidation. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of some novel thiazole substituted benzotriazole derivatives
  作者：Nitin D. Gaikwad、Sachin V. Patil、Vivek D. Bobade

  DOI：10.1016/j.bmcl.2012.03.094

  日期：2012.5

  A series of novel hybrid molecules 4a-y containing thiazole and benzotriazole templates were designed and synthesized. The structures of the synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR and mass spectral data. All the synthesized compounds were tested for their antimicrobial activity (zone of inhibition) against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. After that minimum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and minimum fungicidal concentrations (MFCs) of all the synthesized compounds were determined. The investigation of antimicrobial screening data revealed that most of the tested compounds showed moderate to good microbial inhibitions. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis, In Vitro α-Glucosidase Inhibitory Activity and Molecular Docking Study of New Benzotriazole-Based Bis-Schiff Base Derivatives
  作者：Imran Khan、Wajid Rehman、Fazal Rahim、Rafaqat Hussain、Shoaib Khan、Srosh Fazil、Liaqat Rasheed、Muhammad Taha、Syed Adnan Ali Shah、Magda H. Abdellattif、Thoraya A. Farghaly

  DOI：10.3390/ph16010017

  日期：——

  This study was carried out to synthesize benzotriazole-based bis-Schiff base scaffolds (1–20) and assess them in vitro for α-glucosidase inhibitory potentials. All the synthetics analogs based on benzotriazole-based bis-Schiff base scaffolds were found to display an outstanding inhibition profile on screening against the α-glucosidase enzyme. The synthetic scaffolds showed a varied range of inhibition

  本研究旨在合成基于苯并三唑的双席夫碱支架 (1-20)，并在体外评估它们的 α-葡萄糖苷酶抑制潜力。发现所有基于苯并三唑基双席夫碱支架的合成类似物在筛选 α-葡萄糖苷酶时都显示出出色的抑制作用。与作为标准药物的阿卡波糖（IC50 = 10.30 ± 0.20 µM）相比，合成支架显示出不同范围的抑制曲线，IC50 值从 1.10 ± 0.05 µM 到 28.30 ± 0.60 µM 不等。在该系列中，十五个支架 1-3、5、6、9-16、18-20 被确定比标准阿卡波糖更有效，而其余五个支架 4、7、8、16 和 17 也显示出效力抗α-葡萄糖苷酶，但发现其效力低于标准阿卡波糖。所有新合成的支架的结构都使用不同的光谱技术（如 HREI-MS 和 1H-和 13C-NMR 光谱）进行了确认。为了找到结构-活性关系，进行了分子对接研究以了解活性抑制剂与酶活性位点的结合模式，结果支持实验数据。