4-iodo-2-nitroaniline | 20289-35-4

• 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-iodo-2-nitroaniline
• 英文别名: 5-iodo-2-nitro-aniline；5-Jod-2-nitro-anilin；5-Iodo-2-nitroaniline
• CAS: 20289-35-4
• 化学式: C₆H₅IN₂O₂
• 分子量: 264.022
• InChiKey: FQPPKORVTBLTBX-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±32.0 °C(Predicted)
• 密度：
  2.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-iodo-2-nitroaniline 在 镍 、 甲苯 作用下， 生成 5-碘-1,3-二氢苯并咪唑-2-酮
  参考文献：
  名称：

  Feitelson et al., Journal of the Chemical Society, 1952, p. 2389,2393

  摘要：

  DOI：
• 作为产物：
  描述：

  4-碘-1,2-二硝基-苯 在 乙醇 、 氨 作用下， 生成 4-iodo-2-nitroaniline
  参考文献：
  名称：

  Wender, Gazzetta Chimica Italiana, 1889, vol. 19, p. 233

  摘要：

  DOI：

文献信息

• Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols
  作者：Ramachandra Reddy Putta、Simin Chun、Seok Beom Lee、Junhwa Hong、Dong-Chan Oh、Suckchang Hong

  DOI：10.1039/d1ra02532e

  日期：——

  one-pot synthesis of quinoxalines via transfer hydrogenative condensation of 2-nitroanilines with vicinal diols. The tricarbonyl (η4-cyclopentadienone) iron complex, which is well known as the Knölker complex, catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding carbonyl and 1,2-diaminobenzene intermediates were generated in situ. Trimethylamine N-oxide was used

  在这里，我们报道了通过2-硝基苯胺与邻二醇的转移氢化缩合，铁催化一锅法合成喹喔啉。三羰基(η4-环戊二烯酮)铁络合物，即众所周知的Knölker络合物，催化醇的氧化和硝基芳烃的还原，并原位生成相应的羰基和1,2-二氨基苯中间体。三甲胺 N-氧化物用于活化铁络合物。各种不对称和对称邻位二醇用于转移氢化，得到喹喔啉衍生物，产率为 49-98%。基于一系列控制实验提出了一种合理的机制。该方案的主要优点是不需要外部氧化还原试剂或额外的碱，并且水作为唯一的副产物被释放。
• Glutathione Mediates Control of Dual Differential Bio‐orthogonal Labelling of Biomolecules
  作者：Frederik Peschke、Andrea Taladriz‐Sender、Matthew J. Andrews、Allan J. B. Watson、Glenn A. Burley

  DOI：10.1002/anie.202313063

  日期：2023.12.11

  Traditional approaches to bio‐orthogonal reaction discovery have focused on developing reagent pairs that react with each other faster than they are metabolically degraded. Glutathione (GSH) is typically responsible for the deactivation of most bio‐orthogonal reagents. Here we demonstrate that GSH promotes a Cu‐catalysed (3+2) cycloaddition reaction between an ynamine and an azide. We show that GSH acts as a redox modulator to control the Cu oxidation state in these cycloadditions. Rate enhancement of this reaction is specific for ynamine substrates and is tuneable by the Cu:GSH ratio. This unique GSH‐mediated reactivity gradient is then utilised in the dual sequential bio‐orthogonal labelling of peptides and oligonucleotides via two distinct chemoselective (3+2) cycloadditions.

  摘要发现生物正交反应的传统方法侧重于开发能以比新陈代谢降解更快的速度相互反应的试剂对。谷胱甘肽（GSH）通常会导致大多数生物正交试剂失活。在这里，我们证明 GSH 可促进铜催化的(3+2)环加成反应。我们发现 GSH 可作为氧化还原调节剂，在这些环加成反应中控制铜的氧化态。该反应的速率增强对ynamine底物具有特异性，并可通过Cu:GSH比例进行调节。这种由 GSH 介导的独特反应梯度随后被用于通过两种不同的化学选择性（3+2）环化反应对肽和寡核苷酸进行双序列生物正交标记。
• Discovery of 5-(4-methylpiperazin-1-yl)-2-nitroaniline derivatives as a new class of SIRT6 inhibitors
  作者：Weining Sun、Xiuli Chen、Shenzhen Huang、Wenpei Li、Chenyu Tian、Shengyong Yang、Linli Li

  DOI：10.1016/j.bmcl.2020.127215

  日期：2020.8

  SIRT6 is a deacetylase of histone H3 and inhibitors of SIRT6 have been thought as potential agents for treatment of diabetes. Herein we report the discovery of a series of new SIRT6 inhibitors containing the skeleton 1-phenylpiperazine. Among them, compound 5-(4-methylpiperazin-1-yl)-2-nitroaniline (6d) is the most potent one, which showed an IC50 value of 4.93 mu M against SIRT6 in the Fluor de Lys (FDL) assay. It displayed K-D values of 9.76 mu M and 10 mu M in surface plasmon resonance (SPR) and isothermal titration calorimetry (ITC) assays, respectively. In selectivity assay, 6d showed no activity against other members of the HDAC family (SIRT1-3 and HDAC1-11) at concentrations up to 200 mu M. In a mouse model of type 2 diabetes, 6d could significantly increase the level of glucose transporter GLUT-1, thereby reducing blood glucose. Overall, this study provides a promising lead compound for subsequent drug discovery targeting SIRT6.