2-(1H-咪唑-1-基)-1-(4-硝基苯基)-乙酮 | 37910-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(1H-咪唑-1-基)-1-(4-硝基苯基)-乙酮
• 英文名称: 2-(1H-imidazol-1-yl)-1-(4-nitrophenyl) ethanone
• 英文别名: 2-(1H-imidazol-1-yl)-1-(4-nitrophenyl)ethanone；α-imidazolyl-(4-nitroacetophenone)；N-(4-nitrophenacyl)imidazole；2-Imidazol-1-yl-1-(4-nitrophenyl)ethanone
• CAS: 37910-79-5
• 化学式: C₁₁H₉N₃O₃
• mdl: MFCD00688187
• 分子量: 231.211
• InChiKey: SBPGWXSTCFNGPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1H-咪唑-1-基)-1-(4-硝基苯基)-乙酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以79%的产率得到1-(4-氨基苯基)-2-(1H-咪唑-1-基)乙酮
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer

  摘要：

  A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 mu M) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 mu M. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC50 1.7 mu M and 0.27 mu M, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.042
• 作为产物：
  描述：

  咪唑 、 2-溴-4'-硝基苯乙酮 以 丙酮 为溶剂， 反应 12.0h， 以93%的产率得到2-(1H-咪唑-1-基)-1-(4-硝基苯基)-乙酮
  参考文献：
  名称：

  氨基酮的合成及抗菌作用

  摘要：

  传染病病原体中对许多抗生素和化学制剂的抗性广泛分布，使得寻找化学治疗剂，特别是氨基酮及其盐系列变得非常紧迫。为了进一步（参见[i-4]）确定氨基酮的结构-生物活性的依赖性，我们合成了一系列氨基酮（1）-（VII）的卤化氢（表i）并进行了对它们对革兰氏阳性和革兰氏阴性微生物的五种参考菌株的抗菌作用的研究（表 2）。

  DOI：

  10.1007/bf00764817

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
• One pot synthesis of <scp> α‐ <i>N</i> </scp> ‐heteroaryl ketone derivatives from aryl ketones using aqueous <scp> NaICl ₂ </scp>
  作者：Shrikant M. Ghodse、Navnath T. Hatvate、Vikas N. Telvekar

  DOI：10.1002/jhet.4412

  日期：2022.4

  A simple and efficient method for the synthesis of α-heteroaryl ketones from aryl ketones and amine using aqueous sodium dichloroiodate is established. This method is mild, operationally simple, has a short reaction time, and easy workup procedure to afford the corresponding α-N-heteroaryl ketone derivatives in moderate to good yield.

  建立了一种使用二氯碘酸钠水溶液从芳基酮和胺合成α-杂芳基酮的简单有效的方法。该方法温和、操作简单、反应时间短、后处理容易，以中等至良好的收率得到相应的α- N-杂芳基酮衍生物。
• 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。
• An Efficient and Convenient Method for Synthesis of 1-Substituted Imidazoles
  作者：Fung Fuh Wong、Chun Min Lin、Jiann-Jyh Huang、Mou-Yung Yeh

  DOI：10.3987/com-06-10726

  日期：——
• Salerno; Sorrenti; Guerrera, Pharmazie, 1999, vol. 54, # 9, p. 685 - 690
  作者：Salerno、Sorrenti、Guerrera、Sarva、Siracusa、Di Giacomo、Vanella

  DOI：——

  日期：——