(E)-2-{3-(4-fluorophenyl)-4-[(hydroxyimino)methyl]-1H-pyrazol-1-yl}-1,3-benzothiazole-6-sulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-2-{3-(4-fluorophenyl)-4-[(hydroxyimino)methyl]-1H-pyrazol-1-yl}-1,3-benzothiazole-6-sulfonamide
• 英文别名: 2-[3-(4-fluorophenyl)-4-[(E)-hydroxyiminomethyl]pyrazol-1-yl]-1,3-benzothiazole-6-sulfonamide
• 化学式: C₁₇H₁₂FN₅O₃S₂
• 分子量: 417.444
• InChiKey: AXXWWYHZBZVCMD-DNTJNYDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-hydrazinobenzothiazole-6-sulfonic acid amide 在 盐酸 、 乙醇 、 盐酸羟胺 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-2-{3-(4-fluorophenyl)-4-[(hydroxyimino)methyl]-1H-pyrazol-1-yl}-1,3-benzothiazole-6-sulfonamide 、 (E)-2-{3-(4-fluorophenyl)-4-[(hydroxyimino)methyl]-1H-pyrazol-1-yl}-1,3-benzothiazole-6-sulfonamide
  参考文献：
  名称：

  4-Functionalized 1,3-diarylpyrazoles bearing 6-aminosulfonylbenzothiazole moiety as potent inhibitors of carbonic anhydrase isoforms hCA I, II, IX and XII

  摘要：

  A series of 24 novel heterocyclic compounds-functionalized at position 4 with aldehyde (5a-5f), carboxylic acid (6a-6f), nitrile (7a-7f) and oxime (8a-8f) functional groups-bearing 6-aminosulfonybenzothiazole moiety at position 1 of pyrazole has been synthesized and investigated for the inhibition of four isoforms of the alpha-class carbonic anhydrases (CAs, EC 4.2.1.1), comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (transmembrane, tumor associated isozymes). Against the human isozyme hCA I, compounds 6a-6f showed medium-weak inhibitory potential with Ki values in the range of 157-690 nM with 6a showing better potential than the standard drug acetazolamide (AZA). Against hCA II, all the compounds showed excellent to moderate inhibition with Ki values of compounds 5a, 5d, 5f, 6a-6f, 8d and 8f lower than 12 nM (Ki of AZA). Against hCA IX, all the compounds showed moderate inhibition with the exception of 6e which showed nearly 9 fold a better profile compared to AZA, whereas against hCA XII, four compounds 6e, 7a, 7b and 7d showed Ki in the same order as that of AZA. Carboxylic acid 6e was found to be an excellent inhibitor of both hCA IX and XII, with Ki values of 2.8 nM and 5.5 nM, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.018