1H-吡唑-4-磺酸 | 438630-65-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 1H-吡唑-4-磺酸
• 英文名称: pyrazole-4-sulfonic acid
• 英文别名: 1H-pyrazole-4-sulfonic acid；1H-Pyrazol-4-sulfonsaeure；1H-pyrazol-2-ium-4-sulfonate
• CAS: 438630-65-0
• 化学式: C₃H₄N₂O₃S
• 分子量: 148.142
• InChiKey: XGCDCDCJNZFVSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1H-吡唑-4-磺酸 在 五氯化磷 作用下， 反应 1.0h， 生成 4-氯磺酰基吡唑
  参考文献：
  名称：

  Potent and Selective Nonpeptidic Inhibitors of Procollagen C-Proteinase

  摘要：

  6-Cyclohexyl-N-hydroxy-3-(1,2,4-oxadiazol-5-yl)hexanamides were previously disclosed as inhibitors of procollagen C-proteinase (PCP) culminating in the identification of amide 1. Our objective was to discover a second inhibitor that would have improved affinity for PCP and to optimize properties for transepidermal delivery (TED) to intact skin. Further investigation of this template identified a number of potent PCP inhibitors (IC50 values of 2-6 nM) with improved TED flux. Sulfonamide 56 had excellent PCP enzyme activity when measured with a peptide substrate (K-i 8.7 nM) or with the endogenous substrate procollagen (IC50 3.4 nM) and demonstrates excellent selectivity over MMPs involved in wound healing (> 10 000-fold). In the fibroplasia model, 56 inhibited deposition of insoluble collagen by 76 +/- 2% at 10 mu M and was very effective at penetrating human skin in vitro with a TED flux of 1.5 mu g/cm(2)/h, which compares favorably with values for agents that are known to penetrate skin well in vivo. Based on this profile, 56 (UK-421,045) was selected as a candidate for further preclinical evaluation as a topically applied, dermal anti-scarring agent.

  DOI：

  10.1021/jm061010z
• 作为产物：
  描述：

  吡唑 在 硫酸 、 三氧化硫 作用下， 反应 5.0h， 以73%的产率得到1H-吡唑-4-磺酸
  参考文献：
  名称：

  [EN] HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES
  [FR] QUINONES ROBUSTES SOLUBLES DANS L'EAU À POTENTIEL FAIBLE ET ÉLEVÉ

  摘要：

  本文披露了取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌和蒽氢醌。取代的对苯二酚和邻苯二酚的化学式为：而取代的1,4-喹啉醌或1,2-喹啉醌具有相应的氧化结构（1,4-苯醌和1,2-苯醌）。R1、R2、R3和R4中的一个或多个包括磺酸酯基、磺酰胺基或膦酸酯基，而不包括这些基团之一的R1、R2、R3和R4包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、腈、酰亚胺、吡唑或其组合。取代的蒽醌的化学式为：而取代的蒽氢醌具有相应的还原结构。R1-R8中的一个或多个通过硫醚、胺或醚与环相连，包括一个或多个烷基。不含这些基团之一的R1-R8包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、羟基、烷氧基、醚、胺或氢的任何基团。取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌或蒽氢醌在水中溶解，在水酸性溶液中稳定，并且在氧化形式中具有有用的还原电位。因此，它们可以用作新兴技术中的氧化还原中介体，例如在介导燃料电池或有机介质流动电池中。

  公开号：

  WO2018160618A1

文献信息

• 3-ox(adi) azolylpropanohydroxamic acids useful as procollagen C- Proteinase inhibitors
  申请人：——

  公开号：US20020151535A1

  公开（公告）日：2002-10-17

  Compounds of formula (I): 1 wherein the substituents are as defined herein, and their salt, solvates, and prodrugs are procollagen C-proteinase (PCP) inhibitors useful in treating conditions mediated by PCP.

  式（I）的化合物： 其中取代基如本文所定义，并且它们的盐、溶剂合物和前药是用于治疗由PCP介导的疾病的前胶原C蛋白酶（PCP）抑制剂。
• Synthesis and Structure-Activity Relationships of a New Series of Benzimidazoles as H1-Antihistaminic Agents.
  作者：Maria Rosa CUBERES、Montserrat CONTIJOCH、Carme CALVET、Julia ALEGRE、Jordi Ramon QUINTANA、Jordi FRIGOLA

  DOI：10.1248/cpb.45.1287

  日期：——

  New 2-(4-(4-azolybutyl)piperazinyl)-, 2-(4-(4-azolybutyl)piperazinylmethyl)-, 2-(4-(4-azolylbutyl)homopiperazinyl)- and 2-(4-(4-azolylbutyl)homopiperazinyl)methylbenzimidazoles were synthesized, characterized and tested for in vitro and in vivo H1-antihistaminic activity. Structure-activity relationships impleid that the best antihistaminic activity required the simultaneous presence of a homopiperazinylbenzimidazole system (or a methylene linker between the benzimidazole and the piperazine rings) and an unsubstituted pyrazole ring. 1-(2-Ethoxyethyl)-2-4-[4-(pyrazol-l-yl)butyl]homopiperazin-l-yl}benzimidazole (17), at its dimaleate salt, has been chosen for further development.

  对新的 2-(4-(4-偶氮丁基)哌嗪基)-、2-(4-(4-偶氮丁基)哌嗪基甲基)-、2-(4-(4-偶氮丁基)均哌嗪基)- 和 2-(4-(4-偶氮丁基)均哌嗪基)甲基苯并咪唑进行了合成、表征和体内外 H1 抗组胺活性测试。结构-活性关系表明，最佳抗组胺活性需要同时存在均哌嗪基苯并咪唑体系（或苯并咪唑环和哌嗪环之间的亚甲基连接体）和未取代的吡唑环。我们选择了 1-（2-乙氧基乙基）-2-4-[4-（吡唑-1-基）丁基]均哌嗪-1-基}苯并咪唑（17）的二马来酸盐进行进一步开发。
• Cation effect on the inorganic–organic layered structure of pyrazole-4-sulfonate networks and inhibitory effects on copper corrosion
  作者：Isurika R. Fernando、Nikos Daskalakis、Konstantinos D. Demadis、Gellert Mezei

  DOI：10.1039/b9nj00361d

  日期：——

  The present study demonstrates that the pyrazole-4-sulfonate anion (4-SO3-pzH = L−) is a versatile ligand for the preparation of layered, 3-D solid state lattices. The ligand itself can coordinate to metals with both its sulfonate group and aromatic N-atom, as well as participate in hydrogen bonding both as donor and acceptor, and form various extended π–π networks. Five new complexes with Rb+, Cs+, Mg2+, Sr2+ and Cu2+ have been prepared and characterized including single crystal X-ray diffraction: RbL, tetragonal I41/a, a = 9.7332(4) Å, b = 9.7332(4) Å, c = 29.941(1) Å, V = 2836.5(2) Å, Z = 16; CsL, monoclinic P21/c, a = 8.821(1) Å, b = 8.109(1) Å, c = 9.889(2) Å, β = 91.560(3)°, V = 707.1(2) Å, Z = 4; Mg(H2O)6L2, triclinic P, a = 7.0543(7) Å, b = 7.7307(8) Å, c = 8.6389(9) Å, α = 72.572(2)°, β = 74.370(2)°, γ = 76.045(2)°, V = 426.22(8) Å, Z = 1; SrL2, triclinic P, a = 6.027(2) Å, b = 7.243(3) Å, c = 14.186(5) Å, α = 92.491(8)°, β = 101.383(7)°, γ = 97.471(7)°, V = 426.22(8) Å, Z = 2; Cu(H2O)2L2·4H2O, monoclinic P21/c, a = 9.032(1) Å, b = 13.297(1) Å, c = 7.7103(9) Å, β = 109.747(2)°, V = 871.5(2) Å, Z = 2. The varying size and charge of the cations in these five complexes produce unique, alternating inorganic–organic layered materials. We find a correlation between the size and charge of cations and the coordination mode of the ligand as well as hydration of the metal, but no correlation between the nature of the cation and the thickness of the inorganic/organic layers. We conclude that the overall 3-D structure of these layered materials is determined by a subtle balance between the coordination preferences of the metal ion and an intricate lattice of hydrogen bonds and aromatic interactions. Ligand HL and its complexes with Na, K, Rb, Cs, Mg, Ca, Sr and Ba were tested as potential corrosion inhibitors of copper metal surfaces at three different pH values (2, 3, and 4). All the above mentioned compounds show significant corrosion inhibition at pH 4 and 3, while no activity is observed at pH 2. The correlation of inhibition activity with pH of ligand HL and its different metal complexes is discussed.

  本研究表明，吡唑-4-磺酸阴离子（4-SO3-pzH = Lâ）是一种多功能配体，可用于制备层状三维固态晶格。配体本身可以通过其磺酸盐基团和芳香 N 原子与金属配位，也可以作为供体和受体参与氢键作用，并形成各种扩展的 ÏâÏ 网络。我们制备了五种与 Rb+、Cs+、Mg2+、Sr2+ 和 Cu2+ 的新配合物，并对其进行了单晶 X 射线衍射表征：RbL, tetragonal I41/a, a = 9.7332(4) à , b = 9.7332(4) à , c = 29.941(1) à , V = 2836.5(2) à , Z = 16; CsL, monoclinic P21/c, a = 8.821(1) à , b = 8.109(1) à , c = 9.889(2) à , δ = 91.560(3)°, V = 707.1(2) à , Z = 4; Mg(H2O)6L2, 三斜 P, a = 7.0543(7) à , b = 7.7307(8) à , c = 8.6389(9) à , δ = 72.572(2)°, δ = 74.370(2)°, δ³ = 76.045(2)°, V = 426.22(8) à , Z = 1; SrL2, 三菱 P, a = 6.027(2) à , b = 7.243(3) à , c = 14.186(5) à , δ± = 92.491(8)°, δ² = 101.383(7)°, δ³ = 97.471(7)°, V = 426.22(8) à , Z = 2; Cu(H2O)2L2Â-4H2O, 单斜 P21/c, a = 9.032(1) à , b = 13.297(1) à , c = 7.7103(9) à , δ² = 109.747(2)°, V = 871.5(2) à , Z = 2.这五种络合物中阳离子的大小和电荷的变化产生了独特的、交替的无机有机层状材料。我们发现阳离子的大小和电荷与配体的配位模式以及金属的水合作用有关，但阳离子的性质与无机/有机层的厚度无关。我们的结论是，这些层状材料的整体三维结构是由金属离子的配位偏好与氢键和芳香族相互作用的复杂晶格之间的微妙平衡决定的。配体 HL 及其与 Na、K、Rb、Cs、Mg、Ca、Sr 和 Ba 的配合物作为铜金属表面的潜在缓蚀剂，在三个不同的 pH 值（2、3 和 4）下进行了测试。讨论了配体 HL 及其不同金属配合物的抑制活性与 pH 值的相关性。
• 3-ox(adi)azolylpropanohydroxamic acids useful as procollagen C-proteinase inhibitors
  申请人：——

  公开号：US20040142986A1

  公开（公告）日：2004-07-22

  Compounds of formula (I): 1 wherein the substituents are as defined herein, and their salt, solvates, and prodrugs are procollagen C-proteinase (PCP) inhibitors useful in treating conditions mediated by PCP.

  式(I)的化合物：其中取代基如此处所定义，以及它们的盐、溶剂合物和前药是前胶原C蛋白酶（PCP）抑制剂，可用于治疗由PCP介导的疾病。
• Unsaturated Sulfonic Acids. V.¹ Addition of Diazomethane and Phenyl Azide to Derivatives of Ethylenesulfonic Acid and its Homologs²
  作者：Christian S. Rondestvedt、Pauline K. Chang

  DOI：10.1021/ja01629a036

  日期：1955.12