4-(3-(4-chlorophenyl)-4-formyl-1H-pyrazol-1-yl)benzenesulfonamide | 1135953-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-(4-chlorophenyl)-4-formyl-1H-pyrazol-1-yl)benzenesulfonamide
• CAS: 1135953-03-5
• 化学式: C₁₆H₁₂ClN₃O₃S
• 分子量: 361.809
• InChiKey: RPGMBDVVSAMUPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.05
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(3-(4-chlorophenyl)-4-formyl-1H-pyrazol-1-yl)benzenesulfonamide 在 氨 、 双氧水 、 碘 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-[4-(aminosulfonyl)phenyl]-3-(4-chlorophenyl)-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII

  摘要：

  A library of 4-functionalized 1,3-diarylpyrazoles (3a-3h, 5a-5g and 6a-6g) was designed, synthesized and evaluated against four human carbonic anhydrase (CA, EC 4.2.1.1) isozymes representing two cytosolic isozymes hCA I and hCA II, and two transmembrane tumor associated ones, hCA IX and hCA XII. All the twenty two tested compounds exhibited excellent CA activity profile against the four CA isozymes when compared to the reference drug acetazolamide. Six of the tested compounds (3a-3b, 3f, 3h, 6a and 6b) displayed low nanomolar affinity (K-i < 5 nM) for hCA IX whereas seven compounds (3a-3b, 3d-3f, 3h and 6f) displayed K-i < 10 nM against hCA XII. In addition, they acted as selective CA inhibitors of isoforms IX and XII over the physiological isoforms I and II. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.023
• 作为产物：
  描述：

  4-[2-[1-(4-Chlorophenyl)ethylidene]hydrazinyl]benzenesulfonamide 在 甲醇 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 4-(3-(4-chlorophenyl)-4-formyl-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  吡唑基苯并[d]咪唑类是碳酸酐酶同工型hCA IX和XII的新型有效和选择性抑制剂。

  摘要：

  设计，合成和评估了新型吡唑基苯并[d]咪唑衍生物（2a-2f），并针对四种属于α家族的人碳酸酐酶同工型，其中包括两个胞质同工型hCA I和II，以及两个跨膜肿瘤相关同工型hCA IX和XII。从显示出高效力但低选择性的这些衍生物开始，支持肿瘤相关同工型hCA IX和XII，我们研究了去除磺酰胺基团的影响。因此，合成了没有磺酰胺部分的类似物3a-3f，并且生物学测定显示出作为与肿瘤相关的hCA IX和hCA XII的抑制剂的良好的活性以及优异的选择性，并且通过分子对接研究对其进行了分析。

  DOI：

  10.1016/j.bmc.2016.04.061

文献信息

• Pyrazole‐4‐carboxylic Acids from Vanadium‐catalyzed Chemical Transformation of Pyrazole‐4‐carbaldehydes
  作者：Renu Bala、Poonam Kumari、Sumit Sood、Harshita Phougat、Anil Kumar、Karan Singh

  DOI：10.1002/jhet.3546

  日期：2019.6

  The conversion of aldehydes into carboxylic acids using oxidizing agents is a common protocol in transformation chemistry. An efficient oxidation strategy of transformation of pyrazole‐4‐aldehydes to the corresponding acids using vanadium catalysts in the presence of 30% H2O2 as an oxidant is described. The catalytic technology was successfully applied to a range of various 4‐formylpyrazoles, and plausible

  使用氧化剂将醛转化为羧酸是转化化学中的常见协议。描述了在30％H 2 O 2作为氧化剂存在下使用钒催化剂将吡唑-4-醛转化为相应酸的有效氧化策略。催化技术已成功地应用于各种4-甲酰基吡唑，并探讨了可能的机理。
• Synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory–antibacterial agents
  作者：Pawan Kumar、Navneet Chandak、Pawan Kaushik、Chetan Sharma、Dhirender Kaushik、Kamal R. Aneja、Pawan K. Sharma

  DOI：10.1007/s00044-011-9853-4

  日期：2012.11

  The present article describes the synthesis of two novel series of thiosemicarbazones 3 and thiazolylhydrazinomethylidenepyrazoles 5. All the newly synthesized target compounds (3a–e and 5a–o) were screened for their in vivo anti-inflammatory (AI) activity using carrageenan-induced rat paw edema assay and in vitro antibacterial activity against two Gram-positive and two Gram-negative bacteria. Eight

  本文介绍了两个新系列的thiosemicarbazones 3和thiazolylhydrazinomethylidenepyrazoles 5的合成。使用角叉菜胶诱导的大鼠爪水肿测定法筛选了所有新合成的目标化合物（3a - e和5a - o）的体内抗炎（AI）活性以及针对两种革兰氏阳性和两种革兰氏阴性的体外抗菌活性。阴性细菌。八个化合物（3b - d，5b，5e，5f，5i和5o）在角叉菜胶注射后3和4 h表现出始终如一的优异AI活性（≥70％抑制作用），与标准药物消炎痛（78％）相当，而其余十二种化合物显示出显着的活性，并在抑制后显示57–75％ 3 h和4 h后抑制56-63％。所有测试的化合物均显示出中等的抗菌性能。
• Synthesis and biological evaluation of some 4-functionalized-pyrazoles as antimicrobial agents
  作者：Pawan K. Sharma、Navneet Chandak、Pawan Kumar、Chetan Sharma、Kamal R. Aneja

  DOI：10.1016/j.ejmech.2011.01.060

  日期：2011.4

  1,3-Diaryl-4-formylpyrazoles 8 bearing benzenesulfonamide moiety at position-1 were synthesized as important intermediates following Vilsmeier-Haack strategy. Aldehyde moiety of 4-formylpyrazole was then converted into carboxylic acid 9, cyano 10 and carbothioamide 11 using established procedures. Out of these 4-functionalized pyrazoles, pyrazole-4-carboxylic acids 9 and carbothioamides 11 were evaluated for their in vitro antibacterial activity against four pathogenic bacterial strains namely, Staphylococcus aureus, Bacillus subtilis (Gram-positive), Escherichia coli, Pseudomonas aeruginosa (Gram-negative), and in vitro antifungal activity against two pathogenic fungal strains namely, Aspergillus niger and Aspergillus flavus. Three tested compounds, 9e, 11b and 11f exhibited moderate antibacterial activity against Gram-positive bacteria and 9g showed moderate antifungal activity against the tested fungi. However, none of the compounds showed any activity against Gram-negative bacteria. (c) 2011 Elsevier Masson SAS. All rights reserved.