4-(4-cyano-3-(p-tolyl)-1H-pyrazol-1-yl)benzenesulfonamide | 1135953-23-9

• 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-(4-cyano-3-(p-tolyl)-1H-pyrazol-1-yl)benzenesulfonamide
• 英文别名: Pyrazolyl benzenesulfonamide derivative, 9b；4-[4-cyano-3-(4-methylphenyl)pyrazol-1-yl]benzenesulfonamide
• CAS: 1135953-23-9
• 化学式: C₁₇H₁₄N₄O₂S
• 分子量: 338.39
• InChiKey: JINQUNXXILDVNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-cyano-3-(p-tolyl)-1H-pyrazol-1-yl)benzenesulfonamide 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以85%的产率得到1-[4-(aminosulfonyl)phenyl]-3-(4-methylphenyl)-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-p-tolylethylidene)hydrazinyl)benzenesulfonamide 在 六氟磷酸钾 、 2,2,6,6-四甲基哌啶氧化物 、 氧气 、 N,N-二甲基甲酰胺 、 六甲基二硅氮烷 、 sodium hydroxide 、 sodium nitrite 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 19.0h， 生成 4-(4-cyano-3-(p-tolyl)-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  轻度的TEMPO催化将醛氧化成腈

  摘要：

  已经开发出一种以六甲基二硅氮烷（HMDS）为氮源，由醛制备腈的有效方法。反应在温和条件下以2,2,6,6-四甲基哌啶-1-氧基（TEMPO）为催化剂，NaNO 2或TBN为助催化剂，分子氧为末端氧化剂。各种芳族，杂芳族，脂族和烯丙基醛都可以良好或优异的产率转化为相应的腈。

  DOI：

  10.1002/adsc.201501130

文献信息

• A practical iodine-catalyzed oxidative conversion of aldehydes to nitriles
  作者：Chaojie Fang、Meichao Li、Xinquan Hu、Weimin Mo、Baoxiang Hu、Nan Sun、Liqun Jin、Zhenlu Shen

  DOI：10.1039/c6ra26435b

  日期：——

  A simple and efficient method for the direct synthesis of nitriles from aldehydes using ammonium acetate as the nitrogen source has been developed. The reactions were performed with iodine as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into their corresponding nitriles

  已经开发出一种简单有效的方法，可以使用乙酸铵作为氮源，从醛类直接合成腈。反应在温和条件下以碘为催化剂，以叔丁基氢过氧化物（TBHP）为氧化剂进行。各种芳族，杂芳族，脂族和烯丙基醛都可以良好或优异的产率转化为相应的腈。
• 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.