4-({4-[(E)-phenyldiazenyl]benzoyl}amino)benzenesulfonic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-({4-[(E)-phenyldiazenyl]benzoyl}amino)benzenesulfonic acid
• 英文别名: 4-(Naphthalene-1-carbonylamino)benzenesulfonic acid；4-(naphthalene-1-carbonylamino)benzenesulfonic acid
• 化学式: C₁₇H₁₃NO₄S
• 分子量: 327.361
• InChiKey: QHXKCCJZWVYEML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 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：
  91.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氨基苯磺酸 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 4-({4-[(E)-phenyldiazenyl]benzoyl}amino)benzenesulfonic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of suramin-derived dual antagonists of the proinflammatory G protein-coupled receptors P2Y2 and GPR17

  摘要：

  Dual- or multi-target drugs are particularly promising for the treatment of complex diseases such as (neuro)inflammatory disorders. In the present study, we identified dual antagonists for two related proinflammatory G protein-coupled receptors (GPCRs), the purinergic receptor P2Y(2) receptor, and the orphan receptor GPR17. Based on the lead compound suramin small molecules were designed, synthesized, and modified, including benzenesulfonate, benzenesulfonamide, dibenzamide and diphenylurea derivatives. Structure-activity relationship studies identified 3-nitrophenyl 4-benzamidobenzenesulfonic acid derivatives as dual P2Y(2)R/GPR17 antagonists. In particular, 3-nitrophenyl 4-(4-chlorobenzamido) benzenesulfonate (14l, IC50 3.01 mu M at P2Y(2)R, and 3.37 mu M at GPR17) and 3-nitrophenyl-4-(2-chlorobenzamido)benzenesulfonate (14m, IC50 3.17 mu M at P2Y(2)R, and 1.67 mu M at GPR17) exhibited dual antagonistic activity. Compound 14l was shown to act as an allosteric antagonist at both receptors. In addition, GPR17-selective antagonists were identified( )including 3-nitrophenyl 4-benzamidobenzenesulfonate (14a, IC50 3.20 mu M) and 3-nitrophenyl 4-(3-(trifluoromethyl)benzamido) benzenesulfonate (14f, IC50 3.88 mu M). The developed antagonists were selective versus other closely related P2Y receptors. They were found to possess high chemical and metabolic stability in human liver microsomes and therefore present good starting points for developing potent multi-target drugs with potential applications in inflammatory diseases. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111789

文献信息

• Efficient Synthesis of Readily Water-Soluble Amides Containing Sulfonic Groups
  作者：Krzysztof R. Idzik、Karsten Nödler、Tobias Licha

  DOI：10.1080/00397911.2013.794900

  日期：2014.1.2

  A series of various readily water-soluble amides were synthesized by different procedures. These compounds are useful chemical tracers for assessing the cooling progress in a georeservoir during geothermal power plant operation. Acylation of primary amines was carried out by basically employing the Schotten-Baumann method. As a second method a single-phase solvent system consisting of ethyl acetate as an organic solvent and triethylamine as a catalyst was used. Products were characterized by H-1 NMR and C-13 NMR. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Design, synthesis and biological evaluation of suramin-derived dual antagonists of the proinflammatory G protein-coupled receptors P2Y2 and GPR17
  作者：Thanigaimalai Pillaiyar、Mario Funke、Haneen Al-Hroub、Stefanie Weyler、Sabrina Ivanova、Jonathan Schlegel、Aliaa Abdelrahman、Christa E. Müller

  DOI：10.1016/j.ejmech.2019.111789

  日期：2020.1

  Dual- or multi-target drugs are particularly promising for the treatment of complex diseases such as (neuro)inflammatory disorders. In the present study, we identified dual antagonists for two related proinflammatory G protein-coupled receptors (GPCRs), the purinergic receptor P2Y(2) receptor, and the orphan receptor GPR17. Based on the lead compound suramin small molecules were designed, synthesized, and modified, including benzenesulfonate, benzenesulfonamide, dibenzamide and diphenylurea derivatives. Structure-activity relationship studies identified 3-nitrophenyl 4-benzamidobenzenesulfonic acid derivatives as dual P2Y(2)R/GPR17 antagonists. In particular, 3-nitrophenyl 4-(4-chlorobenzamido) benzenesulfonate (14l, IC50 3.01 mu M at P2Y(2)R, and 3.37 mu M at GPR17) and 3-nitrophenyl-4-(2-chlorobenzamido)benzenesulfonate (14m, IC50 3.17 mu M at P2Y(2)R, and 1.67 mu M at GPR17) exhibited dual antagonistic activity. Compound 14l was shown to act as an allosteric antagonist at both receptors. In addition, GPR17-selective antagonists were identified( )including 3-nitrophenyl 4-benzamidobenzenesulfonate (14a, IC50 3.20 mu M) and 3-nitrophenyl 4-(3-(trifluoromethyl)benzamido) benzenesulfonate (14f, IC50 3.88 mu M). The developed antagonists were selective versus other closely related P2Y receptors. They were found to possess high chemical and metabolic stability in human liver microsomes and therefore present good starting points for developing potent multi-target drugs with potential applications in inflammatory diseases. (C) 2019 Elsevier Masson SAS. All rights reserved.