4-acetyl-3-nitrobenzoic acid | 79481-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-3-nitrobenzoic acid
• CAS: 79481-75-7
• 化学式: C₉H₇NO₅
• 分子量: 209.158
• InChiKey: XHCPXLLKEYHTPB-UHFFFAOYSA-N

物化性质

• 沸点：
  423.9±35.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-acetyl-3-nitrobenzoic acid 在 4-二甲氨基吡啶 、 tin(II) chloride dihdyrate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-butyl 3-methylbenzo[c]isoxazole-6-carboxylate
  参考文献：
  名称：

  Synthetic, structural mimetics of the β-hairpin flap of HIV-1 protease inhibit enzyme function

  摘要：

  Small-molecule mimetics of the beta-hairpin flap of HIV-1 protease (HIV-1 PR) were designed based on a 1,4-benzodiazepine scaffold as a strategy to interfere with the flap-flap protein-protein interaction, which functions as a gated mechanism to control access to the active site. Michaelis-Menten kinetics suggested our small-molecules are competitive inhibitors, which indicates the mode of inhibition is through binding the active site or sterically blocking access to the active site and preventing flap closure, as designed. More generally, a new bioactive scaffold for HIV-1PR inhibition has been discovered, with the most potent compound inhibiting the protease with a modest K-i of 11 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.002
• 作为产物：
  描述：

  对乙基苯甲酸 在 chromium(VI) oxide 、 硝酸 、 高碘酸 作用下， 以 乙腈 为溶剂， 反应 24.5h， 生成 4-acetyl-3-nitrobenzoic acid
  参考文献：
  名称：

  光不稳定 α-甲基硝基苄基化合物的简单合成

  摘要：

  摘要 与在苄基位置缺乏 α-甲基取代的硝基苄基化合物相比，α-甲基硝基苄基化合物显示出优异的光化学释放特性。4-(1-羟基-乙基)-3-硝基-苯甲酸乙酯和4-(1-氨基-乙基)-3-硝基-苯甲酸乙酯的合成分四步进行。在乙腈中用 3 mol% 三氧化铬/高碘酸将 4-乙基-3-硝基-苯甲酸有效氧化为 4-乙酰-3-硝基-苯甲酸提供了一种常见的可结晶前体，其中羟基和胺取代的 α可合成-甲基硝基苄基化合物。这种氧化方法可用于合成广泛的硝基苄基保护基团。

  DOI：

  10.1081/scc-120039491

文献信息

• Asthma and allergic inflammation modulators
  申请人：Fu Zice

  公开号：US20080085891A1

  公开（公告）日：2008-04-10

  Compounds, pharmaceutical compositions and methods are provided that are useful in the treatment of inflammatory and immune-related diseases and conditions. In particular, the invention provides compounds which modulate the function and/or expression of proteins involved in atopic diseases, inflammatory conditions and cancer. The subject compounds are carboxylic acid derivatives.

  本发明提供了在治疗炎症和免疫相关疾病和病况方面有用的化合物、制药组合物和方法。特别是，本发明提供了调节参与过敏性疾病、炎症病况和癌症的蛋白质的功能和/或表达的化合物。所述化合物为羧酸衍生物。
• High-Yielding and Photolabile Approaches to the Covalent Attachment of Biomolecules to Surfaces via Hydrazone Chemistry
  作者：Ju Hun Lee、Dylan W. Domaille、Hyunwoo Noh、Taeseok Oh、Chulmin Choi、Sungho Jin、Jennifer N. Cha

  DOI：10.1021/la500744s

  日期：2014.7.22

  The development of strategies to couple biomolecules covalently to surfaces is necessary for constructing sensing arrays for biological and biomedical applications. One attractive conjugation reaction is hydrazone formation the reaction of a hydrazine with an aldehyde or ketone as both hydrazines and aldehydes/ketones are largely bioorthogonal, which makes this particular reaction suitable for conjugating biomolecules to a variety of substrates. We show that the mild reaction conditions afforded by hydrazone conjugation enable the conjugation of DNA and proteins to the substrate surface in significantly higher yields than can be achieved with traditional bioconjugation techniques, such as maleimide chemistry. Next, we designed and synthesized a photocaged aryl ketone that can be conjugated to a surface and photochemically activated to provide a suitable partner for subsequent hydrazone formation between the surface-anchored ketone and DNA- or protein-hydrazines. Finally, we exploit the latent functionality of the photocaged ketone and pattern multiple biomolecules on the same substrate, effectively demonstrating a strategy for designing substrates with well-defined domains of different biomolecules. We expect that this approach can be extended to the production of multiplexed assays by using an appropriate mask with sequential photoexposure and biomolecule conjugation steps.
• US7321001B2
  申请人：——

  公开号：US7321001B2

  公开（公告）日：2008-01-22
• US7541383B2
  申请人：——

  公开号：US7541383B2

  公开（公告）日：2009-06-02
• Synthetic, structural mimetics of the β-hairpin flap of HIV-1 protease inhibit enzyme function
  作者：Jay Chauhan、Shen-En Chen、Katherine J. Fenstermacher、Aurash Naser-Tavakolian、Tali Reingewertz、Rosene Salmo、Christian Lee、Emori Williams、Mithun Raje、Eric Sundberg、Jeffrey J. DeStefano、Ernesto Freire、Steven Fletcher

  DOI：10.1016/j.bmc.2015.09.002

  日期：2015.11

  Small-molecule mimetics of the beta-hairpin flap of HIV-1 protease (HIV-1 PR) were designed based on a 1,4-benzodiazepine scaffold as a strategy to interfere with the flap-flap protein-protein interaction, which functions as a gated mechanism to control access to the active site. Michaelis-Menten kinetics suggested our small-molecules are competitive inhibitors, which indicates the mode of inhibition is through binding the active site or sterically blocking access to the active site and preventing flap closure, as designed. More generally, a new bioactive scaffold for HIV-1PR inhibition has been discovered, with the most potent compound inhibiting the protease with a modest K-i of 11 mu M. (C) 2015 Elsevier Ltd. All rights reserved.