4-[2-[1-(4-Chlorophenyl)ethylidene]hydrazinyl]benzenesulfonamide | 363597-29-9

• 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-[2-[1-(4-Chlorophenyl)ethylidene]hydrazinyl]benzenesulfonamide
• CAS: 363597-29-9
• 化学式: C₁₄H₁₄ClN₃O₂S
• 分子量: 323.803
• InChiKey: OQEHIRQHFIDZSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  磺胺 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 11.0h， 生成 4-[2-[1-(4-Chlorophenyl)ethylidene]hydrazinyl]benzenesulfonamide
  参考文献：
  名称：

  吡唑-香豆素和吡唑-喹啉查尔酮作为潜在的抗结核药物

  摘要：

  吡唑、香豆素和喹啉是医学上重要的部分。在这项研究中，使用多步反应合成了两个系列的新型吡唑-香豆素查耳酮和吡唑-喹啉查耳酮。所有合成的化合物都使用不同的光谱技术进行了很好的表征，包括 1 H 和 13 C 核磁共振、高分辨率质谱和电喷雾电离质谱。使用微孔板 Alamar Blue 测定评估化合物对结核分枝杆菌 H37Rv 菌株的抗结核活性，并确定化合物的最小抑制浓度 (MIC)。在 32 种测试化合物中，化合物 3e、3u 和 7h 的 MIC 值为 3.125 µg/ml，并且发现它们是无毒的。化合物与酶 DprE1 的分子对接研究揭示了可能的作用机制。查耳酮衍生物表现出介于 -7.047 和 -9.353 kcal/mol 之间的结合亲和力值。使用薛定谔软件的 QikProp 模块预测 ADME 参数，这些化合物表现出良好的药理和口服吸收特性。

  DOI：

  10.1002/ardp.202000077

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。
• Metal- and solvent-free synthesis of N-sulfonylformamidines
  作者：Nisha Chandna、Navneet Chandak、Pawan Kumar、Jitander K. Kapoor、Pawan K. Sharma

  DOI：10.1039/c3gc40797g

  日期：——

  A solvent-free green synthesis of N-sulfonylformamidines is reported via the direct condensation of N,N-dimethylformamide dimethyl acetal (DMF-DMA) and sulfonamide derivatives at room temperature. The described method avoids the use of metal catalysts as well as hazardous solvents, which are not permitted for pharmaceutical manufacture, for the reactions or isolation of products. Hence, the current work presents a fast and efficient alternative to earlier reported methods. The mild nature of the procedure is demonstrated by varied functional group tolerance.

  报道了一种无溶剂的绿色合成N-磺酰基甲酰胺的方案，通过在室温下直接冷凝N,N-二甲基甲酰胺二甲基缩醛(DMF-DMA)和磺酰胺衍生物。该方法避免了使用金属催化剂以及对药物生产不允许的危险溶剂，从而用于反应或产品的分离。因此，目前的工作提供了一种比之前报道的方法更快速高效的替代方案。该程序的温和特性通过不同功能团的耐受性得到了验证。
• 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.
• Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects
  作者：Halise Inci Gul、Kaan Kucukoglu、Cem Yamali、Sinan Bilginer、Hafize Yuca、Iknur Ozturk、Parham Taslimi、Ilhami Gulcin、Claudiu T. Supuran

  DOI：10.3109/14756366.2015.1047359

  日期：2016.7.3

  In this study, 4-(2-substituted hydrazinyl)benzenesulfonamides were synthesized by microwave irradiation and their chemical structures were confirmed by H-1 NMR, (CNMR)-C-13, and HRMS. Ketones used were: Acetophenone (S1), 4-methylacetophenone (S2), 4-chloroacetophenone (S3), 4-fluoroacetophenone (S4), 4-bromoacetophenone (S5), 4-methoxyacetophenone (S6), 4-nitroacetophenone (S7), 2-acetylthiophene (S8), 2-acetylfuran (S9), 1-indanone (S10), 2-indanone (S11). The compounds S9, S10 and S11 were reported for the first time, while S1-S8 was synthesized by different method than literature reported using microwave irradiation method instead of conventional heating in this study. The inhibitory effects of 4-(2-substituted hydrazinyl) benzenesulfonamide derivatives (S1-S11) against hCA I and II were studied. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized sulphonamide derivatives with K-is in the range of 1.79 +/- 0.22-2.73 +/- 0.08 nM against hCA I and in the range of 1.72 +/- 0.58-11.64 +/- 5.21nM against hCA II, respectively.
• Pyrazolylbenzo[ d ]imidazoles as new potent and selective inhibitors of carbonic anhydrase isoforms hCA IX and XII
  作者：Satish Kumar、Mariangela Ceruso、Tiziano Tuccinardi、Claudiu T. Supuran、Pawan K. Sharma

  DOI：10.1016/j.bmc.2016.04.061

  日期：2016.7

  were designed, synthesized and evaluated against four human carbonic anhydrase isoforms belonging to α family comprising of two cytosolic isoforms hCA I and II as well as two transmembrane tumor associated isoforms hCA IX and XII. Starting from these derivatives that showed high potency but low selectivity in favor of tumor associated isoforms hCA IX and XII, we investigated the impact of removing the

  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。