N-(4-hydroxyphenyl)naphthalene-1-sulfonamide | 50994-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-hydroxyphenyl)naphthalene-1-sulfonamide
• CAS: 50994-44-0
• 化学式: C₁₆H₁₃NO₃S
• 分子量: 299.35
• InChiKey: UNYQJVDUBYREST-UHFFFAOYSA-N

物化性质

• 沸点：
  531.4±52.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxyphenyl)naphthalene-1-sulfonamide 在 SiO₂-supported NaIO₄ 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78%的产率得到N-(4-oxocyclohexa-2,5-dien-1-ylidene)naphthalene-1-sulfonamide
  参考文献：
  名称：

  发现4-氨基-2-（硫代）苯酚衍生物作为新型蛋白激酶和血管生成抑制剂，用于治疗癌症：合成和生物学评估。第二部分

  摘要：

  合成了一系列新颖的4-氨基-2-（硫代）苯酚衍生物。初步的生物学测试表明，与以前的工作相比，几种化合物具有较高的特异性蛋白激酶和血管生成抑制活性，这主要是因为用磺酰胺结构取代了酰胺片段。其中，化合物5i被鉴定为有效抑制蛋白激酶B / AKT（IC 50  = 1.26μM）和ABL酪氨酸激酶（IC 50  = 1.50μM）。同时，化合物5i在人脐静脉内皮细胞（HUVEC）管形成试验和大鼠胸主动脉环试验中均显示出对Pazopanib具有竞争性的体外抗血管生成活性。

  DOI：

  10.1016/j.ejmech.2013.07.056
• 作为产物：
  描述：

  C₂₃H₁₆ClNO₄S 在 甲醇 、 potassium carbonate 作用下， 以74.7 mg的产率得到N-(4-hydroxyphenyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  在室温下将苯甲酸简单实用地转化为酚类

  摘要：

  酚类是重要的有机分子，因为它们在许多领域都有广泛的应用。本文报道了一种在室温下通过简单的有机试剂从苯甲酸制备酚类的有效实用方法。这种方法与各种官能团和杂环兼容，并且可以轻松放大。为了证明其合成效用，生物活性分子和不对称六芳基苯已通过利用这种转变作为战略步骤来制备。机理研究表明，关键的迁移步骤涉及游离碳正离子而不是自由基中间体。考虑到苯甲酸的丰富性和酚类的实用性，预计该方法将在有机合成中得到广泛的应用。

  DOI：

  10.1021/jacs.2c07529

文献信息

• N-substituted benzyl or phenyl aromatic sulfamides compounds and the use thereof
  申请人：Shanghai Institute of Materia Medica Chinese Academy of Science

  公开号：US06605635B1

  公开（公告）日：2003-08-12

  N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)benzyl aromatic sulfonamides and N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)phenyl aromatic sulfonamides compounds in accordance with the animal test, are active in the prevention and the treatment of cardiac arrhythmia. These compounds are prepared as corresponding diamines by the condensation of optionally substituted aromatic sulfochlorides with p-hydroxybenzylamine, p-aminophenol, or the like, which followed by the Mannich reaction of the resulted corresponding aromatic sulfamides with formaldehyde and secondary amines; or directly obtained by the reaction of the aromatic sulfamides with 4-amino-2,6-bis-disubstituted aminomethylphenol. Subsequently, the diamines are reacted with various acids to provide their salts.

  根据动物实验，N-(3,5-双取代氨甲基-4-羟基)苯甲基芳香磺酰胺和N-(3,5-双取代氨甲基-4-羟基)苯基芳香磺酰胺化合物对预防和治疗心律失常具有活性。这些化合物通过选择性取代的芳香基磺酰氯与对羟基苯甲胺、对氨基苯酚等缩合生成相应的二胺，随后与甲醛和二级胺进行Mannich反应，或直接与4-氨基-2,6-双取代氨甲基苯酚反应制备而成。随后，二胺与各种酸反应制备它们的盐。
• N-SUBSTITUTED BENZYL OR PHENYL AROMATIC SULFAMIDES COMPOUNDS AND THE USE THEREOF
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP1245561A1

  公开（公告）日：2002-10-02

  N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)benzyl aromatic sulfonamides and N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)phenyl aromatic sulfonamides compounds in accordance with the animal test, are active in the prevention and the treatment of cardiac arrhythmia. These compounds are prepared as corresponding diamines by the condensation of optionally substituted aromatic sulfochlorides with p-hydroxybenzylamine, p-aminophenol, or the like, which followed by the Mannich reaction of the resulted corresponding aromatic sulfamides with formaldehyde and secondary amines; or directly obtained by the reaction of the aromatic sulfamides with 4-amino-2,6-bis-disubstituted aminomethylphenol. Subsequently, the diamines are reacted with various acids to provide their salts.

  根据动物试验，N-(3,5-二取代氨甲基-4-羟基)苄基芳香族磺酰胺和 N-(3,5-二取代氨甲基-4-羟基)苯基芳香族磺酰胺化合物在预防和治疗心律失常方面具有活性。这些化合物是通过任选取代的芳香族磺酰氯与对羟基苄胺、对氨基苯酚或类似物缩合，然后将生成的相应芳香族磺酰胺与甲醛和仲胺进行曼尼希反应制备成相应的二胺；或者直接通过芳香族磺酰胺与 4-氨基-2,6-二取代氨甲基苯酚反应制备成二胺。随后，二胺与各种酸反应生成它们的盐。
• INK FOR SCRATCH COLORING AND SHEET WITH INVISIBLE INFORMATION PRINTED
  申请人：Mitsubishi Paper Mills Limited

  公开号：EP2096149A1

  公开（公告）日：2009-09-02

  Disclosed are a scratch color-developable ink comprising an electron-donating colorless or light-color dye precursor, an electron-accepting color developer and a varnish, wherein a solid particle component contained therein has an average particle diameter of 0.3 to 25 µm, a scratch color-developable ink comprising an electron-donating colorless or light-color dye precursor, an electron-accepting color developer and a varnish, wherein an azaphthalide compound is contained as the electron-donating colorless or light-color dye precursor, and an invisible information printed sheet obtained by printing invisible information on a support with the above scratch color-developable ink. The above scratch color-developable ink makes invisible information visible easily by scratching with a finger nail although the color of an invisible information printed portion is hard to develop by frictional contact during usual handling, gives a high developed color intensity and is free from the occurrence of dust during the visualization of invisible information.

  公开了一种由电子捐献型无色或浅色染料前体、电子接受型显色剂和光油组成的划痕显色墨水，其中包含的固体颗粒成分的平均颗粒直径为 0.3至25微米；一种可刮擦显色油墨，由电子捐赠的无色或浅色染料前体、电子接受的显色剂和光油组成，其中含有作为电子捐赠的无色或浅色染料前体的萘化合物；以及一种通过在支撑物上用上述可刮擦显色油墨印刷隐形信息而获得的隐形信息印刷品。 上述划痕显色油墨虽然在通常的操作过程中通过摩擦接触很难使隐形信息印刷部分显色，但用指甲划痕即可轻松显现隐形信息，显色强度高，而且在显现隐形信息时不会产生灰尘。
• Electrochemical Cross-Coupling between <i>N</i>-(4-Hydroxyphenyl)-sulfonamides and 2-Naphthols: Synthesis of 2,2′-Bis(arenol)s
  作者：Zheng Zhu、Yanan Li、Shitang Ma、Xuan Zhou、Yekai Huang、Jianan Sun、Wei-Yi Ding

  DOI：10.1021/acs.joc.4c00021

  日期：——

  herein present an electrochemical method for the dehydrogenative cross-coupling of N-(4-hydroxyphenyl)-sulfonamides and 2-naphthols. This transformation provides a direct and scalable approach to a wide range of C1-symmetric 2,2′-bis(arenol)s with moderate to high yields under mild conditions. Preliminary attempts with the asymmetric variant of this reaction were also performed with ≤55% ee for the synthesis

  我们在此提出了一种用于 N-（4-羟基苯基）-磺胺类药物和 2-萘酚脱氢交叉偶联的电化学方法。这种转化为在温和条件下以中高产率分析各种 C1 对称 2,2′-双（芳烃醇）提供了一种直接且可扩展的方法。还用 ≤55% ee 对该反应的不对称变体进行了初步尝试，以合成 2,2′-双（芳烃醇）。进行了对照实验以提出一种合理的反应机制。
• NOVEL SULFONAMIDES AS RADIOSENSITIZERS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0462179A1

  公开（公告）日：1991-12-27