2-[(4-Sulfamoylphenyl)formamido]acetic acid | 143288-21-5

• 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: 2-[(4-Sulfamoylphenyl)formamido]acetic acid
• 英文别名: 2-[(4-sulfamoylbenzoyl)amino]acetic acid
• CAS: 143288-21-5
• 化学式: C₉H₁₀N₂O₅S
• mdl: MFCD08445033
• 分子量: 258.255
• InChiKey: UEFOOXBQBNWTDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(4-Sulfamoylphenyl)formamido]acetic acid 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Benzenesulfonamide-peptide conjugates as probes for secondary binding sites near the active site of carbonic anhydrase

  摘要：

  Libraries of N-(4-sulfamoylbenzoyl)oligoglycines terminated with different L-amino acids were screened to identify tight binding inhibitors of human carbonic anhydrase II. Inhibitors terminated with hydrophobic amino acids showed significant enhancements in binding compared to the corresponding glycine derivatives. No enhancements were observed due to polar interactions.

  DOI：

  10.1016/0960-894x(96)00069-8
• 作为产物：
  描述：

  对羧基苯磺酰胺 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.0h， 生成 2-[(4-Sulfamoylphenyl)formamido]acetic acid
  参考文献：
  名称：

  用于集成识别和报告的多功能多肽平台：用于蛋白质-配体相互作用分析的亲和力阵列。

  摘要：

  报道了用于蛋白质检测和定量的分子平台，其中识别已与直接监测靶标蛋白质结合整合在一起。该平台基于多功能的42个残基的螺旋-环-螺旋多肽，该多肽二聚形成四个螺旋束，并允许在可单独寻址的赖氨酸残基的侧链上进行识别和报道分子的位点选择性修饰。模型目标蛋白碳酸酐酶与其抑制剂苯磺酰胺之间的良好相互作用被用于概念验证。设计了亲和力阵列，其中将具有脂族或寡甘氨酸间隔基的苯磺酰胺衍生物和荧光丹磺酰基报告基团引入支架中。阵列成员对人碳酸酐酶II（HCAII）的亲和力是通过用目标蛋白滴定来确定的，并且发现其高度受间隔子的特性影响（解离常数Kd = 0.02-3 microM）。在与苯磺酰胺阵列成员之一的竞争实验中确定了HCAII对乙酰唑酰胺（Kd = 4 nM）的亲和力，以解决为新的靶蛋白结合剂筛选物质库的可能性。同样，成功地区分不同的碳酸酐酶同工酶之间的亲和力突出了执行将来的亚型表达谱分析的可能性。预计我们的

  DOI：

  10.1002/chem.200305391

文献信息

• Carbonic anhydrase inhibitors: 4-sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoyl-benzenecarboxamides with strong topical antiglaucoma properties
  作者：Francesco Mincione、Michele Starnotti、Luca Menabuoni、Andrea Scozzafava、Angela Casini、Claudiu T. Supuran

  DOI：10.1016/s0960-894x(01)00303-1

  日期：2001.7

  4-carboxy-benzenesulfonamide or 4-chloro-3-sulfamoyl benzoic acid with carboxy-protected amino acids/dipeptides, or aromatic/heterocyclic sulfonamides/mercaptans afforded the corresponding benzene-carboxamide derivatives. These were tested as inhibitors of three carbonic anhydrase (CA) isozymes, CA I, II and IV. Some of the new derivatives showed affinity in the low nanomolar range for isozymes CA II

  4-羧基-苯磺酰胺或4-氯-3-氨磺酰基苯甲酸与羧基保护的氨基酸/二肽，或芳族/杂环磺酰胺/硫醇的反应得到相应的苯甲酰胺衍生物。测试了它们作为三种碳酸酐酶（CA）同功酶CA I，II和IV的抑制剂。一些新的衍生物对同工酶CA II和IV表现出低纳摩尔范围的亲和力，参与眼内房水的分泌，并在血压正常和青光眼兔中作为局部作用的抗青光眼药物进行了测试。与临床上使用的药物多佐胺和布林酰胺相比，这些衍生物中的一些衍生物具有良好的体内活性和延长的作用时间。
• Lack of Effect of the Length of Oligoglycine- and Oligo(ethylene glycol)-Derived para-Substituents on the Affinity of Benzenesulfonamides for Carbonic Anhydrase II in Solution
  作者：Ahamindra Jain、Shaw G. Huang、George M. Whitesides

  DOI：10.1021/ja00091a005

  日期：1994.6

  Using H-1 NMR spectroscopy, values of T-2 have been determined for the methylene protons of the oligoglycine moieties of para-substituted benzenesulfonamides having structures H2NO2SC6H4CO(Gly)(n)OH (n = 1-6) bound at the active site of bovine carbonic anhydrase II (CA, EC 4.2.1.1). These values have been correlated with measurements of dissociation constants of these complexes, in order to infer motion of these ligands when bound to the enzyme. Motion of glycines 1-3 (those closest to the aryl ring) is hindered by their proximity to the protein; motion of glycines 4-6 is relatively unhindered. Despite the restriction to motion inferred for glycines 1-3, the values of K-d for the six compounds (n = 1-6, 1-6) are indistinguishable within experimental uncertainty (+/-20%): K-d in mu M (n) 0.30 (1); 0.26 (2); 0.33 (3); 0.37 (4); 0.37 (5); 0.34 (6). There is, therefore, an unexpected compensation of the loss in conformational entropy on binding by another contributor to the free energy.
• A Versatile Polypeptide Platform for Integrated Recognition and Reporting: Affinity Arrays for Protein–Ligand Interaction Analysis
  作者：Karin Enander、Gunnar T. Dolphin、Bo Liedberg、Ingemar Lundström、Lars Baltzer

  DOI：10.1002/chem.200305391

  日期：2004.5.17

  A molecular platform for protein detection and quantification is reported in which recognition has been integrated with direct monitoring of target-protein binding. The platform is based on a versatile 42-residue helix-loop-helix polypeptide that dimerizes to form four-helix bundles and allows site-selective modification with recognition and reporter elements on the side chains of individually addressable

  报道了用于蛋白质检测和定量的分子平台，其中识别已与直接监测靶标蛋白质结合整合在一起。该平台基于多功能的42个残基的螺旋-环-螺旋多肽，该多肽二聚形成四个螺旋束，并允许在可单独寻址的赖氨酸残基的侧链上进行识别和报道分子的位点选择性修饰。模型目标蛋白碳酸酐酶与其抑制剂苯磺酰胺之间的良好相互作用被用于概念验证。设计了亲和力阵列，其中将具有脂族或寡甘氨酸间隔基的苯磺酰胺衍生物和荧光丹磺酰基报告基团引入支架中。阵列成员对人碳酸酐酶II（HCAII）的亲和力是通过用目标蛋白滴定来确定的，并且发现其高度受间隔子的特性影响（解离常数Kd = 0.02-3 microM）。在与苯磺酰胺阵列成员之一的竞争实验中确定了HCAII对乙酰唑酰胺（Kd = 4 nM）的亲和力，以解决为新的靶蛋白结合剂筛选物质库的可能性。同样，成功地区分不同的碳酸酐酶同工酶之间的亲和力突出了执行将来的亚型表达谱分析的可能性。预计我们的
• Benzenesulfonamide-peptide conjugates as probes for secondary binding sites near the active site of carbonic anhydrase
  作者：George B. Sigal、George M. Whitesides

  DOI：10.1016/0960-894x(96)00069-8

  日期：1996.3

  Libraries of N-(4-sulfamoylbenzoyl)oligoglycines terminated with different L-amino acids were screened to identify tight binding inhibitors of human carbonic anhydrase II. Inhibitors terminated with hydrophobic amino acids showed significant enhancements in binding compared to the corresponding glycine derivatives. No enhancements were observed due to polar interactions.