4-(benzoylamino)benzenesulfonic acid | 6052-43-3

• 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-(benzoylamino)benzenesulfonic acid
• 英文别名: N-benzoyl-sulfanilic acid；N-Benzoyl-sulfanilsaeure；4-Benzamino-benzol-sulfonsaeure-(1)；N-Benzoyl-anilin-sulfonsaeure-(4)；4-Benzamidobenzenesulfonic acid
• CAS: 6052-43-3
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: BENAOQZABXENIF-UHFFFAOYSA-N

物化性质

• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 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：
  91.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-重氮基-1-[4-硝基苯基]-乙酮 、 4-(benzoylamino)benzenesulfonic acid 生成 N-benzoyl-sulfanilic acid-(4-nitro-phenacyl ester)
  参考文献：
  名称：

  Notes: The Use of Substituted α-Diazoacetophenones for the Preparation of Derivatives of Sulfonic Acids, NBenzoylated Aminocarboxylic and Aminosulfonic Acids, N-Benzoylated Aminophenols and an N-Benzoylated Amino Thiol

  摘要：

  DOI：

  10.1021/jo01094a601
• 作为产物：
  描述：

  对氨基苯磺酸 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-(benzoylamino)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

• Brine-Mediated Efficient Benzoylation of Primary Amines and Amino Acids
  作者：Gautam Chattopadhyay、Suchandra Chakraborty、Chandan Saha

  DOI：10.1080/00397910802250929

  日期：2008.11.3

  Abstract Benzoylation of primary amines and amino acids is efficiently carried out in a brine solution using a stoichiometric amount of benzoyl chloride followed by trituration with aqueous saturated bicarbonate solution.

  摘要 伯胺和氨基酸的苯甲酰化在盐水溶液中使用化学计量的苯甲酰氯有效地进行，然后用饱和碳酸氢盐水溶液研磨。
• Phosphazo Compounds and their Use in Preparing Amides
  作者：H. W. Grimmel、A. Guenther、Jack F. Morgan

  DOI：10.1021/ja01208a001

  日期：1946.4
• Catalysis of sulfonate ester hydrolysis by an intramolecular amide group assistance
  作者：Sergio Thea、Giuseppe Guanti、Andrew R. Hopkins、Andrew Williams

  DOI：10.1021/jo00218a019

  日期：1985.9
• Josephson, Biochemische Zeitschrift, 1933, vol. 264, p. 441,445, 446
  作者：Josephson

  DOI：——

  日期：——
• 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.]