5-氨基-1-萘磺酰胺盐酸盐 | 32327-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-氨基-1-萘磺酰胺盐酸盐
• 英文名称: 5-amino-1-naphthalene sulfonamide
• 英文别名: 5-aminonaphthalene-1-sulfonamide；p-aminonaphthalein sulfonamide；5-amino-naphthalene-1-sulfonic acid amide；5-Amino-naphthalin-1-sulfonsaeure-amid；5-aminonaphthalene-1-sulphonamide；1-Amino-naphthalin-sulfonamid-5
• CAS: 32327-47-2
• 化学式: C₁₀H₁₀N₂O₂S
• 分子量: 222.268
• InChiKey: OSLAXMFJCQKHFS-UHFFFAOYSA-N

物化性质

• 熔点：
  259 °C
• 沸点：
  499.4±37.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  5-氨基-1-萘磺酰胺盐酸盐 、 对醛基苯甲酸 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以47%的产率得到
  参考文献：
  名称：

  New fluorescent probes for carbonic anhydrases

  摘要：

  我们报告了作为碳酸酐酶活性位点探针的萘磺酰胺衍生物的合成和荧光特性。

  DOI：

  10.1039/b701421j
• 作为产物：
  描述：

  5-acetamidonaphthalene-1-sulfonic acid 生成 5-氨基-1-萘磺酰胺盐酸盐
  参考文献：
  名称：

  Boldyrew, Sb. Statei Obshch. Khim., 1953, p. 616,622

  摘要：

  DOI：

文献信息

• Sigma 2 Receptor Ligands and Therapeutic Uses Therefor
  申请人：Mach Robert H.

  公开号：US20080161343A1

  公开（公告）日：2008-07-03

  A series of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs are disclosed, as well as methods of their preparation. Their affinities for sigma (σ1 and σ2) receptors are described. Two new compounds, N-(9-(4-aminobutyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate and N-(9-(6-aminohexyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate, are shown to have a high affinity and selectivity for σ2 versus σ1 receptors. Among the disclosed compounds are biotinylated and fluorescent analogs. These compounds can serve as probes to the σ2 receptor. In addition, some disclosed compounds can induce apoptotic cell death by both caspase-dependent and caspase-independent mechanisms, and are effective for treatment of tumors. The compounds can be used as chemotherapeutics or chemosensitizers in the treatment of a wide variety of solid tumors.

  本文披露了一系列N-取代的9-氮杂双环[3.3.1]壬烷-3α-基苯基氨基甲酸酯类似物，以及它们的制备方法。描述了它们对sigma（σ1和σ2）受体的亲和力。展示了两种新化合物，即N-(9-(4-氨基丁基)-9-氮杂双环[3.3.1]壬烷-3α-基)-N′-(2-甲氧基-5-甲基苯基)氨基甲酸酯和N-(9-(6-氨基己基)-9-氮杂双环[3.3.1]壬烷-3α-基)-N′-(2-甲氧基-5-甲基苯基)氨基甲酸酯，它们被证明对σ2受体具有高亲和力和选择性，而非σ1受体。在披露的化合物中包括生物素化和荧光类似物。这些化合物可以作为对σ2受体的探针。此外，一些披露的化合物可以通过半胱氨酸依赖和半胱氨酸非依赖机制诱导凋亡细胞死亡，并且对肿瘤的治疗有效。这些化合物可以用作治疗各种固体肿瘤的化疗药物或化疗增敏剂。
• Using Quenching Kinetics and Thermodynamics of Amino-Fluorophores as Empirical Tools for Predicting Boronic Acid Sensors Suitable for Use in Physiological Conditions
  作者：Nicholas McGregor、Christophe Pardin、W. G. Skene

  DOI：10.1071/ch11297

  日期：——

  A series of water-soluble 1-amino-naphthalenes and 2-amino-fluorenes are prepared. These serve as model fluorophores for measuring the thermodynamics and kinetics of fluorescence quenching with phenylboronic acids and aliphatic amines. Steady-state and time-resolved fluorescence quenching kinetics are investigated using the Stern–Volmer method. Diffusion limited quenching constants and exergonic thermodynamics of electron transfer are derived for the 5-amino-1-napthol and 2-aminofluorene derivatives with phenylboronic acid and/or an aliphatic imine. No quenching and endergonic thermodynamics or electron transfer are observed for 5-sulfonamide, 5-sulfonic acid, or 5-hydroxy-7-sulfonic acid aminonaphthalene derivatives. Boronic acid sensors synthesized from these aminofluorophores by reductive amination with 2-formylphenylboronic acid undergo fluorescence revival in the presence of saccharides only when the fluorophore demonstrates diffusion limited quenching kinetics and exergonic thermodynamics of electron transfer with the boronic acid or imine quenchers. Thus, these two properties are suitable empirical tools for predicting saccharide-induced fluorescence revival of boronic acid sensors.

  制备了一系列水溶性 1-氨基萘和 2-氨基芴。这些荧光团可作为模型荧光团，用于测量苯硼酸和脂肪族胺的荧光淬灭热力学和动力学。使用 Stern-Volmer 方法研究了稳态和时间分辨荧光淬灭动力学。得出了 5-氨基-1-萘酚和 2-氨基芴衍生物与苯硼酸和/或脂肪族亚胺的扩散受限淬灭常数和电子转移的外功热力学。对于 5-磺酰胺、5-磺酸或 5-羟基-7-磺酸氨基萘衍生物，没有观察到淬灭和内生热力学或电子转移。通过与 2-甲酰基苯硼酸进行还原胺化反应，由这些氨基荧光团合成的硼酸传感器只有在荧光团显示出扩散受限的淬灭动力学以及与硼酸或亚胺淬灭剂进行电子转移的放生热力学时，才会在糖类存在的情况下发生荧光恢复。因此，这两个特性是预测糖诱导的硼酸传感器荧光复苏的合适经验工具。
• Heterocyclic compounds and their preparation and use
  申请人：A/S Ferrosan

  公开号：US04889855A1

  公开（公告）日：1989-12-26

  Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein --A-- together with the two carbon atoms denoted as 1 and 2 is selected from ##STR2## R.sup.1, R.sup.2 and R.sup.3 are independently H, halogen, CN, NH.sub.2, NO.sub.2, SO.sub.3 H, SO.sub.2 NH.sub.2, or CONH.sub.2 The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.

  具有以下式子的杂环二羟基喹喔啉化合物##STR1##其中--A--与标记为1和2的两个碳原子一起从##STR2##中选择，R.sup.1，R.sup.2和R.sup.3独立地为H，卤素，CN，NH.sub.2，NO.sub.2，SO.sub.3 H，SO.sub.2 NH.sub.2或CONH.sub.2。本发明还涉及制备该化合物的方法，其药物组成物以及其用途。这些化合物在治疗兴奋性神经递质过度活跃引起的症状方面是有用的。
• Pyridoquinoxaline compounds and their preparation and use as glutamate
  申请人：A/S Ferrosan

  公开号：US04912108A1

  公开（公告）日：1990-03-27

  Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein --A-- together with the two carbon atoms denoted as 1 and 2 is selected from ##STR2## R.sup.1, R.sup.2 and R.sup.3 are independently H, halogen, CN, NH.sub.2, NO.sub.2, SO.sub.3 H, SO.sub.2 NH.sub.2, or CONH.sub.2 The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.

  具有以下式子的杂环二羟基喹喔啉化合物 ##STR1## 其中--A--与标记为1和2的两个碳原子一起从以下选择 ##STR2## R.sup.1，R.sup.2和R.sup.3独立地为H，卤素，CN，NH.sub.2，NO.sub.2，SO.sub.3 H，SO.sub.2 NH.sub.2或CONH.sub.2。本发明还涉及制备该化合物的方法，其制药组合物以及它们的用途。该化合物在治疗由兴奋性神经递质的过度活跃引起的症状方面是有用的。
• Stabilization of anionic and neutral forms of a fluorophoric ligand at the active site of human carbonic anhydrase I
  作者：Sumathra Manokaran、Jayati Banerjee、Sanku Mallik、D.K. Srivastava

  DOI：10.1016/j.bbapap.2010.06.024

  日期：2010.10

  We synthesized a fluorogenic dansylamide derivative (JB2-48), which fills the entire (15 Å deep) active site pocket of human carbonic anhydrase I, and investigated the contributions of sulfonamide and hydrophobic regions of the ligand structure on the spectral, kinetic, and thermodynamic properties of the enzyme–ligand complex. The steady-state and fluorescence lifetime data revealed that the deprotonation

  我们合成了一种荧光的丹磺酰胺衍生物（JB2-48），该衍生物填充了人类碳酸酐酶I的整个（15Å深）活性位点，并研究了磺酰胺和配体结构的疏水区在光谱，动力学和化学性质上的贡献。酶-配体复合物的热力学性质。稳态和荧光寿命数据表明，酶结合配体的磺酰胺部分去质子化增加了荧光发射强度以及荧光团的寿命。这是通过活性位点的Zn驻地之间的静电相互作用表现2+辅因子，并且配体的带负电荷的磺酰胺基，和这样的相互作用促成约2.2千卡/摩尔（ΔΔ ģ∘）和0.89千卡/摩尔（ΔΔ ģ ‡在分别稳定地与推定的过渡态）能量。我们提供的证据表明，JB2-48的阴离子和中性形式通过酶的互补微观/构象态得以稳定。讨论了本文研究的机理研究在碳酸酐酶抑制剂的原理设计中的意义。