1-(4-硝基苯基)-2-(1,2,4-三唑-1-基)乙酮 | 139370-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-硝基苯基)-2-(1,2,4-三唑-1-基)乙酮
• 英文名称: 4-nitrophenyl-1,2,4-triazol-1-ylmethyl ketone
• 英文别名: 1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone；1-(4-nitrophenyl)-2-(1,2,4-1H-triazol-1-yl)ethanone；1-(4-Nitrophenyl)-2-(1,2,4-triazol-1-yl)ethanone
• CAS: 139370-88-0
• 化学式: C₁₀H₈N₄O₃
• mdl: MFCD00839685
• 分子量: 232.199
• InChiKey: CQAFVMXEPJPFSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  465.2±51.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1-(4-硝基苯基)-2-(1,2,4-三唑-1-基)乙酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 1-(1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylidene)-2-(4-(4-nitrophenyl)thiazol-2-yl)hydrazine
  参考文献：
  名称：

  Hybrids of ravuconazole: Synthesis and biological evaluation

  摘要：

  In continuation of our work on antimicrobial agents, a number of hybrid molecules 4a-y containing thiazole and triazole pharmacophores were designed and synthesized. The structure of the compounds was established by IR, NMR, MS and CHN analysis. All the synthesized compounds were tested for qualitative (Zone of inhibition) and quantitative (MIC) antimicrobial activities against four pathogenic bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa and two pathogenic fungi Candida albicans and Aspergillus niger. Of all the synthesized compounds screened, most of them show potent antimicrobial activity against Gram positive and Gram negative bacteria as well as the fungi species. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.010
• 作为产物：
  描述：

  对硝基苯乙酮 在 溴 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 64.0h， 生成 1-(4-硝基苯基)-2-(1,2,4-三唑-1-基)乙酮
  参考文献：
  名称：

  Synthesis and Antifungal activity of Phenacyl Azoles

  摘要：

  通过杂环与苯甲酰基卤化物反应，制备了一种新的 N-(4-甲氧基苯甲酰基)咪唑和三种新的取代 N-(苯甲酰基)三唑。前者的酮和后者的一个实例被还原成相应的醇。体外筛选了所有六种化合物对两种致病真菌菌株，即白色念珠菌（耐氟康唑）和曲霉菌的抗真菌活性。结果表明，大多数化合物在 100 μg mL-1 和 80 μg mL-1 的浓度下对这两种菌株都有活性，其中一些化合物的活性与对照化合物氟康唑相当。醇类化合物的活性低于相应的酮类化合物。

  DOI：

  10.3184/174751914x14107905836359

文献信息

• Heme Oxygenase Inhibition by 1-Aryl-2-(1H-imidazol-1-yl/1H-1,2,4-triazol-1-yl)ethanones and Their Derivatives
  作者：Gheorghe Roman、Jason Z. Vlahakis、Dragic Vukomanovic、Kanji Nakatsu、Walter A. Szarek

  DOI：10.1002/cmdc.201000120

  日期：2010.9.3

  been concerned with the design of selective inhibitors of heme oxygenases (HO‐1 and HO‐2). The majority of these were based on a four‐carbon linkage of an azole, usually an imidazole, and an aromatic moiety. In the present study, we designed and synthesized a series of inhibition candidates containing a shorter linkage between these groups, specifically, a series of 1‐aryl‐2‐(1H‐imidazol‐1‐yl/1H‐1

  我们研究小组先前的研究一直与血红素加氧酶选择性抑制剂（HO-1和HO-2）的设计有关。其中大多数是基于吡咯（通常是咪唑）和芳族部分的四碳键合。在本研究中，我们设计和合成了一系列抑制候选物，这些抑制物在这些基团之间具有较短的连接，特别是一系列的1-芳基-2-（1 H-咪唑-1-基/ 1 H-1,2,4-三唑-1-基）乙酮及其衍生物。关于HO-1抑制，发现产生最佳结果的芳族部分是卤素取代的残基，例如3-溴苯基，4-溴苯基和3,4-二氯苯基，或烃基残基，例如2-萘基，4-联苯基。 ，4-苄基苯基和4-（2-苯乙基）苯基。在咪唑酮中，发现有五个（36 – 39和44）对两种同功酶非常有效（IC 50 < 5μM）。相对于咪唑酮类，该系列相应的三唑酮的显示四种化合物（54，55，61，和62）的选择性指数> 50，而对HO-1有利。对于唑二氧戊环，发现其中两个（分别为80和85）分别具有2-萘基部分
• Compounds and Methods for Treating Cancer and Diseases of the Central Nervous System
  申请人：Gupta Ajay

  公开号：US20110319459A1

  公开（公告）日：2011-12-29

  Disclosed are compounds of the general formula (I): TC n D  (I), compositions comprising an effective amount of said compounds either alone or in combination with other chemotherapeutic agents, and methods useful for treating or preventing cancer and for inhibiting tumour tissue growth. These compounds attenuate the oxidative damage associated with increased heme-oxygenase activity and can reduce cell proliferation in transformed cells. In addition, the described compounds and compositions are useful as neuroprotectants and for treating or preventing neurodegenerative disorders and other diseases of the central nervous system.

  本发明涉及一般式（I）的化合物：TCnD（I），包括单独使用或与其他化疗药物联合使用的有效量的该化合物的组合物，以及用于治疗或预防癌症和抑制肿瘤组织生长的有用方法。这些化合物减弱了与增加血红素氧合酶活性相关的氧化损伤，并可以减少转化细胞中的细胞增殖。此外，所述化合物和组合物可用作神经保护剂，并用于治疗或预防中枢神经系统的神经退行性疾病和其他疾病。
• 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.
• Krimer, M.Z.; Styngach, E.P.; Rekhter, M.A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 9.2, p. 1545 - 1550
  作者：Krimer, M.Z.、Styngach, E.P.、Rekhter, M.A.、Grushetskaya, G.N.、Uzhavka, Z.N.、et al.

  DOI：——

  日期：——
• Surpateanu, G.; Lungu, N. C.; Avarvari, N., Journal de Chimie Physique et de Physico-Chimie Biologique, 1994, vol. 91, # 10, p. 1648 - 1657
  作者：Surpateanu, G.、Lungu, N. C.、Avarvari, N.、Lablache-Combier, A.、Grandclaudon, P.、Couture, A.

  DOI：——

  日期：——