4-Azido-1-nitro-2-(trifluoromethyl)benzene | 1440512-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Azido-1-nitro-2-(trifluoromethyl)benzene
• 英文别名: 4-azido-1-nitro-2-(trifluoromethyl)benzene
• CAS: 1440512-29-7
• 化学式: C₇H₃F₃N₄O₂
• 分子量: 232.122
• InChiKey: BCMCXBLGBDLJHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-Azido-1-nitro-2-(trifluoromethyl)benzene 在 3-苄基羟乙基甲基噻唑氯化锂 、 叔丁醇 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.08h， 以88%的产率得到5-氨基-2-硝基三氟甲苯
  参考文献：
  名称：

  Catalytic Reduction of ortho- and para-Azidonitrobenzenes via tert-Butoxide Ion Mediated Electron Transfer

  摘要：

  The reduction of a range of substituted azidonitrobenzene derivatives to the corresponding aniline is described. The chemoselective reaction proceeds cleanly and in good yield, generating minimal waste products. The process involves a thiazolium salt derived species which is proposed as a radical anion relay, with tert-butoxide as the stoichiometric reductant.

  DOI：

  10.1055/s-0032-1318216
• 作为产物：
  描述：

  5-氨基-2-硝基三氟甲苯 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.33h， 以76%的产率得到4-Azido-1-nitro-2-(trifluoromethyl)benzene
  参考文献：
  名称：

  Preliminary investigations into triazole derived androgen receptor antagonists

  摘要：

  A range of 1,4-substituted-1,2,3-N-phenyltriazoles were synthesized and evaluated as non-steroidal androgen receptor (AR) antagonists. The motivation for this study was to replace the N-phenyl amide portion of small molecule antiandrogens with a 1,2,3-triazole and determine effects, if any, on biological activity. The synthetic methodology presented herein is robust, high yielding and extremely rapid. Using this methodology a series of 17 N-aryl triazoles were synthesized from commercially available starting materials in less than 3 h. After preliminary biological screening at 20 and 40 mu M, the most promising three compounds were found to display IC50 values of 40-50 mu M against androgen dependent (LNCaP) cells and serve as a starting point for further structure-activity investigations. All compounds in this work were the focus of an in silico study to dock the compounds into the human androgen receptor ligand binding domain (hARLBD) and compare their predicted binding affinity with known antiandrogens. A comparison of receptor-ligand interactions for the wild type and T877A mutant AR revealed two novel polar interactions. One with Q738 of the wild type site and the second with the mutated A877 residue. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.018

文献信息

• Synthesis of trifluoromethyl-substituted N-aryl-poly-1,2,3-triazole derivatives
  作者：A. Sudheer Kumar、Nagarjuna Kommu、Vikas D. Ghule、Akhila K. Sahoo

  DOI：10.1039/c3ta15184k

  日期：——

  spectroscopic methods; the solid state structures of some of the compounds are confirmed by X-ray diffraction techniques. The synthesized materials decompose in the range of 195–308 °C. Most of the –CF3 and –NO2 groups-bearing aryl triazoles exhibit good densities and acceptable detonation characteristics. Some of the fluorine containing polytriazole-bearing compounds showed positive heats of formation.

  报道了–CF 3和–NO 2取代的N-芳基-聚三唑衍生物的合成，表征和物理性质。这些分子是通过在–CF 3取代的芳基叠氮化物和炔烃之间进行可靠的Cu催化的[3 + 2]环加成而制备的，随后是硝化序列，以及由1,2,3引起的卤素基团的碱基促进的亲核取代-三唑。该化合物通过分析和光谱学方法表征。X射线衍射技术证实了某些化合物的固态结构。合成材料在195–308°C的范围内分解。大部分–CF 3和–NO 2带有基团的芳基三唑显示出良好的密度和可接受的爆炸特性。一些含氟聚三唑的化合物显示出正的形成热。
• A comparison of novel organoiridium(III) complexes and their ligands as a potential treatment for prostate cancer
  作者：Samantha C. Hockey、Gregory J. Barbante、Paul S. Francis、Jarrad M. Altimari、Prusothman Yoganantharajah、Yann Gibert、Luke C. Henderson

  DOI：10.1016/j.ejmech.2015.12.035

  日期：2016.2

  A range of 1,4-substituted 2-pyridyl-N-phenyl triazoles were synthesised and evaluated for their anti proliferative properties against lymph node cancer of the prostate (LNCaP) and bone metastasis of prostate cancer (PC-3) cells. Excellent-to-low IC50 values were determined (5.6-250 mu M), and a representative group of 4 ligands were then complexed to iridium(III) giving highly luminescent species. Re-evaluation of these compounds against both cell lines was then undertaken and improved potency (up to 72-fold) was observed, giving IC50 values of 0.36-11 mu M for LNCaP and 0.85-5.9 mu M for PC-3. Preliminary screens for in vivo toxicity were conducted using a zebrafish model showing a wide range of induced toxicity depending of the compound evaluated. Apoptosis and Caspase-3 levels were also determined and showed no statistical difference between some of the treated specimens and the controls. This study may identify novel therapeutic agents for advanced stage of prostate cancer in humans. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Novel 1,4-Substituted-1,2,3-Triazoles as Antitubercular Agents
  作者：Jarrad M. Altimari、Samantha C. Hockey、Helena I. Boshoff、Andaleeb Sajid、Luke C. Henderson

  DOI：10.1002/cmdc.201500051

  日期：2015.5

  AbstractTuberculosis (TB) remains a pressing unmet medical need, particularly with the emergence of multidrug‐resistant and extensively drug‐resistant tuberculosis. Here, a series of 1,4‐substituted‐1,2,3‐triazoles have been synthesized and evaluated as potential antitubercular agents. These compounds were assembled via click chemistry in high crude purity and in moderate to high yield. Of the compounds tested, 12 compounds showed promising antitubercular activity with six possessing minimum inhibitory concentration (MIC) values <10 μg mL−1, and total selectivity for Mycobacterium tuberculosis (Mtb) growth inhibition. A second set of 21 compounds bearing variations on ring C were synthesized and evaluated. This second library gave an additional six compounds displaying MIC values ≤10 μg mL−1 and total selectivity for Mtb growth inhibition. These compounds serve as an excellent starting point for further development of antitubercular therapies.
• Preliminary investigations into triazole derived androgen receptor antagonists
  作者：Jarrad M. Altimari、Birunthi Niranjan、Gail P. Risbridger、Stephanie S. Schweiker、Anna E. Lohning、Luke C. Henderson

  DOI：10.1016/j.bmc.2014.03.018

  日期：2014.5

  A range of 1,4-substituted-1,2,3-N-phenyltriazoles were synthesized and evaluated as non-steroidal androgen receptor (AR) antagonists. The motivation for this study was to replace the N-phenyl amide portion of small molecule antiandrogens with a 1,2,3-triazole and determine effects, if any, on biological activity. The synthetic methodology presented herein is robust, high yielding and extremely rapid. Using this methodology a series of 17 N-aryl triazoles were synthesized from commercially available starting materials in less than 3 h. After preliminary biological screening at 20 and 40 mu M, the most promising three compounds were found to display IC50 values of 40-50 mu M against androgen dependent (LNCaP) cells and serve as a starting point for further structure-activity investigations. All compounds in this work were the focus of an in silico study to dock the compounds into the human androgen receptor ligand binding domain (hARLBD) and compare their predicted binding affinity with known antiandrogens. A comparison of receptor-ligand interactions for the wild type and T877A mutant AR revealed two novel polar interactions. One with Q738 of the wild type site and the second with the mutated A877 residue. (C) 2014 Elsevier Ltd. All rights reserved.
• Catalytic Reduction of ortho- and para-Azidonitrobenzenes via tert-Butoxide Ion Mediated Electron Transfer
  作者：John Moses、James Burnley、Giorgio Carbone

  DOI：10.1055/s-0032-1318216

  日期：——

  The reduction of a range of substituted azidonitrobenzene derivatives to the corresponding aniline is described. The chemoselective reaction proceeds cleanly and in good yield, generating minimal waste products. The process involves a thiazolium salt derived species which is proposed as a radical anion relay, with tert-butoxide as the stoichiometric reductant.