4-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)benzenesulfonamide | 1293980-75-2

• 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-methoxyphenyl)ethylidene)hydrazinyl)benzenesulfonamide
• 英文别名: 4-{2-[1-(4-methoxyphenyl)ethylidene]hydrazino}benzenesulfonamide；4-[2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl]benzenesulfonamide
• CAS: 1293980-75-2
• 化学式: C₁₅H₁₇N₃O₃S
• 分子量: 319.384
• InChiKey: MJYMKMWWFJJKHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  93.78
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)benzenesulfonamide 在 bis(acetylacetonate)oxovanadium 、 双氧水 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 1-[4-(aminosulfonyl)phenyl]-3-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  钒催化的吡唑-4-甲醛的化学转化产生的吡唑-4-羧酸

  摘要：

  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。

  DOI：

  10.1002/jhet.3546
• 作为产物：
  描述：

  4-磺酰胺基苯肼盐酸盐 、 对甲氧基苯乙酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)benzenesulfonamide
  参考文献：
  名称：

  设计，合成塞来昔布-托美汀药物杂种作为选择性和有效的COX-2抑制剂。

  摘要：

  通过Vilsmier-Haack条件合成了三个新系列的二芳基吡唑10b-d和三芳基吡唑衍生物11a-d和12a-d。通过IR，1 H NMR，13 C NMR，质谱和元素分析来确定制备的化合物的结构。合成化合物在COX-2活性位点上的对接可确保其选择性。此外，评估了目标化合物的体外和体内抑制活性。与COX-1同工酶相比，所有化合物对COX-2同工酶的选择性更高，并且具有出色的抗炎活性。化合物11b，11d和12b的抗炎活性最高（分别为67.4％，62.7％，61.4％），致溃疡性（UI = 2.00、2.75、3.25）分别低于消炎痛（UI = 14）和塞来昔布（ UI = 1.75）已从组织病理学研究中确认。

  DOI：

  10.1016/j.bioorg.2019.103029

文献信息

• Synthesis of novel 1,3,4-trisubstituted pyrazoles as anti-inflammatory and analgesic agents
  作者：Fatma A. Ragab、Nagwa M. Abdel Gawad、Hanan H. Georgey、Mona F. Said

  DOI：10.1016/j.ejmech.2013.03.005

  日期：2013.5

  Some novel 1,3,4-trisubstituted pyrazoles were synthesized and screened for their anti-inflammatory and analgesic activities as well as their ulcerogenic liability. They showed anti-inflammatory and analgesic activities with better GIT tolerance than the standard drug phenylbutazone. In addition, IC50 values for 5e and 8e were recorded. Compound 5e was found to be the most active one as anti-inflammatory

  合成了一些新颖的1,3,4-三取代吡唑，并筛选了它们的抗炎和镇痛活性以及致溃疡作用。他们显示出比标准药物苯基丁a具有更好的GIT耐受性的抗炎和镇痛活性。另外，记录了5e和8e的IC 50值。发现化合物5e作为抗炎和止痛剂是最活性的。另一方面，还进行了COX-1 / COX-2同工酶的选择性，对两种同工型均表现出相同的抑制作用。
• 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。
• Exploring novel anticancer pyrazole benzenesulfonamides featuring tail approach strategy as carbonic anhydrase inhibitors
  作者：Rehab F. Ahmed、Walaa R. Mahmoud、Nagwa M. Abdelgawad、Marwa A. Fouad、Mona F. Said

  DOI：10.1016/j.ejmech.2023.115805

  日期：2023.12

  variable groups like sulphamoyl group as in compounds 4a-e, its bioisosteric carboxylic acid as in compounds 5a-e and 8e, ethyl carboxylate ester as in compounds 6a-e and 9a-e, which were designed as potential prodrugs, isothiazole ring as in compound 7, hydrazide derivative 10e, hydroxamic acid derivatives 11a-e and semicarbazide derivatives 12a-c,e. All the synthesized compounds were investigated for

  本研究旨在设计基于吡唑苯磺酰胺核心的有效碳酸酐酶抑制剂（CAI）。合成了九个系列的取代吡唑苯磺酰胺化合物，其具有可变基团，如化合物4a-e中的氨磺酰基、化合物5a-e和8e中的生物等排羧酸、化合物6a-e和 9a-e中的羧酸乙酯，其中被设计为潜在的前药，化合物7中的异噻唑环、酰肼衍生物10e 、异羟肟酸衍生物11a-e和氨基脲衍生物12a-c,e 。研究了所有合成的化合物对两种人 CA 异构体 hCA IX 和 hCA XII 的碳酸酐酶 (CA) 抑制活性，并与乙酰唑胺(AAZ) 进行比较。此外，还根据美国 NCI 方案评估了这些化合物对 60 种癌细胞系的抗癌活性。 化合物4b 、 5b 、 5d 、 5e 、 6b 、 9b 、 9e和11b显示出对 hCA IX 和 hCA XII 两种亚型的显着抑制活性，而6e 、 9d 、 11d和11e仅与乙酰唑胺相比显示出对 hCA XII
• 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.