4-amino-N-(2-hydroxyphenyl)benzenesulfonamide | 116465-58-8

• 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-amino-N-(2-hydroxyphenyl)benzenesulfonamide
• 英文别名: NSC 229583-G；sulfanilic acid-(2-hydroxy-anilide)；Sulfanilsaeure-(2-hydroxy-anilid)；2-Sulfanilamino-phenol
• CAS: 116465-58-8
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: KKOQLOXVLRQIFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 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：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-N-(2-hydroxyphenyl)benzenesulfonamide 在 亚硝酸特丁酯 、 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 生成 4-azido-N-(2-hydroxyphenyl)benzenesulfonamide
  参考文献：
  名称：

  DDX3X Helicase Inhibitors as a New Strategy To Fight the West Nile Virus Infection

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.8b01403
• 作为产物：
  描述：

  对乙酰胺基苯磺酰氯 在 盐酸 、 sodium acetate 作用下， 生成 4-amino-N-(2-hydroxyphenyl)benzenesulfonamide
  参考文献：
  名称：

  Derivatives of 4-Aminobenzenesulfonanilide. I

  摘要：

  DOI：

  10.1021/ja01274a009

文献信息

• [EN] USE OF DDX3 INHIBITORS AS ANTIPROLIFERATIVE AGENTS<br/>[FR] UTILISATION D'INHIBITEURS DE DDX3 EN TANT QU'AGENTS ANTIPROLIFÉRATIFS
  申请人：AZIENDA OSPEDALIERA UNIV SENESE

  公开号：WO2017162834A1

  公开（公告）日：2017-09-28

  The present invention refers to compounds of formula I or II endowed with DDX3 inhibitory activity, relative pharmaceutical compositions and their use as antihyperproliferative agents. (I) or (II)

  这项发明涉及具有DDX3抑制活性的I或II式化合物，相关的药物组合物以及它们作为抗高增殖剂的用途。(I)或(II)
• [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。
• Sulfonamides with hydroxyphenyl moiety: Synthesis, structure, physicochemical properties, and ability to form complexes with Rh(III) ion
  作者：Małgorzata Gawrońska、Mateusz Kowalik、Joanna Duch、Katarzyna Kazimierczuk、Mariusz Makowski

  DOI：10.1016/j.poly.2022.115865

  日期：2022.7

  folic acid synthesis and prevention of the growth and reproduction of bacteria. Even though they have been applied in therapy for more than 75 years, sulfonamides are still the drugs of choice for the treatment of various diseases. The aim of this work was to synthesize and characterize two new sulfonamides hydroxyphenyl moiety and investigate their ability to form complexes with Rh(III). The results

  磺胺类药物是第一个成功合成的抗菌药物。磺胺类药物的抗菌作用机制包括竞争性抑制叶酸合成和阻止细菌的生长和繁殖。尽管磺胺类药物在治疗中的应用已超过 75 年，但仍然是治疗各种疾病的首选药物。这项工作的目的是合成和表征两种新的磺酰胺羟苯基部分，并研究它们与 Rh(III) 形成复合物的能力。最近的研究结果表明，人们越来越关注将潜在的铂族金属离子配合物作为抗癌和抗菌药物的替代品、有希望的候选物。
• Human helicase DDX3 inhibitors as therapeutic agents
  申请人：AZIENDA OSPEDALIERA UNIVERSITARIA SENESE

  公开号：US10941121B2

  公开（公告）日：2021-03-09

  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.

  本发明是指具有式 I 和 II 的 RNA 螺旋酶 DDX3 抑制活性的化合物及其治疗用途，特别是用于治疗病毒性疾病。
• Use of DDX3 inhibitors as antiproliferative agents
  申请人：AZIENDA OSPEDALIERA UNIVERSITARIA SENESE

  公开号：US11000512B2

  公开（公告）日：2021-05-11

  The present invention refers to compounds of formula I or II endowed with DDX3 inhibitory activity, relative pharmaceutical compositions and their use as antihyperproliferative agents. (I) or (II).

  本发明涉及具有 DDX3 抑制活性的式 I 或式 II 化合物、相关药物组合物及其作为抗过增殖剂的用途。(I)或(II)。