4-[3-(4-chlorophenyl)-4-(hydrazinocarbonyl)-1H-pyrazole-1-yl]benzenesulfonamide | 1583315-62-1

• 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-(hydrazinocarbonyl)-1H-pyrazole-1-yl]benzenesulfonamide
• 英文别名: 4-[3-(4-Chlorophenyl)-4-(hydrazinecarbonyl)pyrazol-1-yl]benzenesulfonamide；4-[3-(4-chlorophenyl)-4-(hydrazinecarbonyl)pyrazol-1-yl]benzenesulfonamide
• CAS: 1583315-62-1
• 化学式: C₁₆H₁₄ClN₅O₃S
• 分子量: 391.838
• InChiKey: PAJHSXQQPZAVON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(3-(4-chlorophenyl)-4-formyl-1H-pyrazol-1-yl)benzenesulfonamide 在 potassium permanganate 、 硫酸 、 一水合肼 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 48.0h， 生成 4-[3-(4-chlorophenyl)-4-(hydrazinocarbonyl)-1H-pyrazole-1-yl]benzenesulfonamide
  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