N-(2-hydroxyphenyl)-4-nitrobenzenesulfonamide | 18226-26-1

• 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: N-(2-hydroxyphenyl)-4-nitrobenzenesulfonamide
• 英文别名: N-<2-Hydroxy-phenyl>-4-nitro-benzol-sulfonamid
• CAS: 18226-26-1
• 化学式: C₁₂H₁₀N₂O₅S
• mdl: MFCD00426981
• 分子量: 294.288
• InChiKey: HIOPSLVWFVXQBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyphenyl)-4-nitrobenzenesulfonamide 在 sodium hydroxide 作用下， 生成 2-(4-硝基苯氧基)苯胺
  参考文献：
  名称：

  Kleb,K.G., Angewandte Chemie, 1968, vol. 80, p. 284 - 285

  摘要：

  DOI：
• 作为产物：
  描述：

  4-nitro-N-phenoxybenzenesulfonamide 在 六氟异丙醇 作用下， 反应 24.0h， 以55%的产率得到N-(2-hydroxyphenyl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  六氟异丙醇 (HFIP) 促进的 N-苯氧基磺酰胺重排，用于直接组装邻磺酰胺酚：实验和计算相结合的研究

  摘要：

  邻磺酰胺酚代表了药物和合成化学中一类有吸引力的结构基序。本文开发了一种有效的无金属重排反应，用于通过 HFIP 促进的分子内磺酰胺基团 1,3-迁移构建邻磺酰胺酚。该方案具有反应条件温和、官能团兼容性广、区域选择性好等特点。结合实验机理研究和详细的 DFT 计算，阐明了 HFIP 分子在促进该反应中的关键作用，并且推导出了独特的氢键网络来解释观察到的反应性。

  DOI：

  10.1016/j.tetlet.2021.153601

文献信息

• [EN] HUMAN HELICASE DDX3 INHIBITORS AS THERAPEUTIC AGENTS<br/>[FR] INHIBITEURS D'HÉLICASE DDX3 HUMAINE COMME AGENTS THÉRAPEUTIQUES
  申请人：AZIENDA OSPEDALIERA UNIV SENESE

  公开号：WO2016128541A1

  公开（公告）日：2016-08-18

  The present invention refers to compounds endowed with RNA helicase DDX3 inhibitory activity of formula I and II and their therapeutic use, in particular for the treatment of viral diseases.

  本发明涉及具有RNA解旋酶DDX3抑制活性的化合物I和II的公式及其治疗用途，特别是用于治疗病毒性疾病。
• Synthesis of Dihydrobenzo[1,4]oxazines by Palladium-Catalyzed Cyclization of N-Substituted 2-Aminophenols with Propargylic Carbonates
  作者：Masahiro Yoshida、Shunya Mori、Kenji Matsumoto、Tsukasa Hirokane

  DOI：10.3987/com-19-s(f)40

  日期：——

  The reaction of N-substituted 2-aminophenols with propargylic carbonates in the presence of a palladium-catalyst is described. The functionalized dihydrobenzo[1,4]oxazines were synthesized. The palladium-catalyzed reaction of soft nucleophiles with propargylic compounds is one of the most successful palladium-catalyzed reaction developed to date. For example, a substrate having two nucleophilic moieties

  描述了在钯催化剂存在下 N-取代的 2-氨基苯酚与碳酸炔丙酯的反应。合成了官能化的二氢苯并[1,4]恶嗪。软亲核试剂与炔丙基化合物的钯催化反应是迄今为止开发的最成功的钯催化反应之一。例如，分子内具有两个亲核部分的底物在钯存在下与碳酸炔丙酯反应生成 -烯丙基钯中间体，该中间体进一步与分子内的其他亲核部分反应生成环化产物（方案 1）。虽然我们研究了双亲核试剂与炔丙基化合物的钯催化反应，我们专注于在氨基上具有吸电子取代基的氨基酚的亲核活性。通过在底物中引入亲核氧和氮部分，我们认为可以构建许多生物活性化合物中的常见结构二氢苯并[1,4]恶嗪。在此，我们描述了 N-取代的 2-氨基苯酚 1 与碳酸炔丙酯 2 的钯催化反应，其中构建了二氢苯并 [1,4] 恶嗪 3-5（方案 2）。
• DDX3X Helicase Inhibitors as a New Strategy To Fight the West Nile Virus Infection
  作者：Annalaura Brai、Francesco Martelli、Valentina Riva、Anna Garbelli、Roberta Fazi、Claudio Zamperini、Alessandro Pollutri、Lucia Falsitta、Stefania Ronzini、Laura Maccari、Giovanni Maga、Simone Giannecchini、Maurizio Botta

  DOI：10.1021/acs.jmedchem.8b01403

  日期：2019.3.14

  Increased frequency of arbovirus outbreaks in the last 10 years represents an important emergence for global health. Climate warming, extensive urbanization of tropical regions, and human migration flows facilitate the expansion of anthropophilic mosquitos and the emerging or re-emerging of new viral infections. Only recently the human adenosinetri-phosphatase/RNA helicase X-linked DEAD-box polypeptide 3 (DDX3X) emerged as a novel therapeutic target in the fight against infectious diseases. Herein, starting from our previous studies, a new family of DDX3X inhibitors was designed, synthesized, validated on the target enzyme, and evaluated against the West Nile virus (WNV) infection. Time of addition experiments after virus infection indicated that the compounds exerted their antiviral activities after the entry process, likely at the protein translation step of WNV replication. Finally, the most interesting compounds were then analyzed for their in vitro pharmacokinetic parameters, revealing favorable absorption, distribution, metabolism, and excretion values. The good safety profile together with a good activity against WNV for which no treatments are currently available, make this new class of molecules a good starting point for further in vivo studies.
• HUMAN HELICASE DDX3 INHIBITORS AS THERAPEUTIC AGENTS
  申请人：AZIENDA OSPEDALIERA UNIVERSITARIA SENESE

  公开号：US20180016243A1

  公开（公告）日：2018-01-18

  The present invention refers to compounds endowed with RNA helicase DDX3 inhibitory activity of formula I and II and their therapeutic use, in particular for the treatment of viral diseases.
• Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study
  作者：Yi Wang、Xiaoli Chen、Shuang Lin、Hui Gao、Fu-Xiaomin Liu、Zhi Zhou、Wei Yi

  DOI：10.1016/j.tetlet.2021.153601

  日期：2022.1

  chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted intramolecular sulfonamide group 1,3-migration. This protocol features mild reaction conditions, broad functional group compatibility and good regioselectivity. Combined experimental mechanistic study and detailed DFT calculations clarified the crucial

  邻磺酰胺酚代表了药物和合成化学中一类有吸引力的结构基序。本文开发了一种有效的无金属重排反应，用于通过 HFIP 促进的分子内磺酰胺基团 1,3-迁移构建邻磺酰胺酚。该方案具有反应条件温和、官能团兼容性广、区域选择性好等特点。结合实验机理研究和详细的 DFT 计算，阐明了 HFIP 分子在促进该反应中的关键作用，并且推导出了独特的氢键网络来解释观察到的反应性。