4-(5-amino-4-(2-(2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-1H-pyrazol-1-yl)benzenesulfonamide

• 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-(5-amino-4-(2-(2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-1H-pyrazol-1-yl)benzenesulfonamide
• 英文别名: 4-[5-amino-4-[[(2-oxoindol-3-yl)amino]carbamoyl]pyrazol-1-yl]benzenesulfonamide
• 化学式: C₁₈H₁₅N₇O₄S
• 分子量: 425.428
• InChiKey: BEDHGUHWDPLEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  174.56
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4-磺酰胺基苯肼盐酸盐 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 生成 4-(5-amino-4-(2-(2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII

  摘要：

  New series of benzenesulfonamide derivatives incorporating pyrazole and isatin moieties were prepared using celecoxib as lead molecule. Biological evaluation of the target compounds was performed against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) and more precisely against the human isoforms hCA I, II (cytosolic), IX and XII (transmembrane, tumor-associated enzymes). Most of the tested compounds efficiently inhibited hCA I, II and IX, with K(1)s of 2.5-102 nM, being more effective than the reference drug acetazolamide. Compounds 11e, 11f, 16e and 16f were found to inhibit hCA XII with Ki of 3.7, 6.5, 5.4 and 7.2 nM, respectively. Compounds lie and 16e, with 5-NO2 substitution on the isatin ring, were found to be selective inhibitors of hCA IX and hCA XII. Docking studies revealed that the NO2 group of both compounds participate in interactions with Asp132 within the hCA IX active site, and with residues Lys67 and Asp130 in hCA XII, respectively. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.021