3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)benzenesulfonamide
• 英文别名: 3-(4-oxo-2-sulfanylidene-1H-quinazolin-3-yl)benzenesulfonamide
• 化学式: C₁₄H₁₁N₃O₃S₂
• 分子量: 333.392
• InChiKey: PXBJMZQLELJETO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  间氨基苯磺酰胺 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII

  摘要：

  We report a series of novel metanilamide-based derivatives 3a-q bearing the 2-mercapto-4-oxo-4H-quinazolin-3-yl moiety as tail. All compounds were synthesized by means of straightforward condensation procedures and were investigated in vitro for their inhibition potency against the human (h) carbonic anhydrase (CA; EC 4.2.1.1.1) isoforms I, II, IX and XII. Among all compounds tested the 6-iodo 3g and the 7-fluoro 3i derivatives were the most potent inhibitors against the tumor associated CA IX and XII isoform (K(1)s 1.5 and 2.7 nM respectively for the hCA IX and K1s 0.57 and 1.9 nM respectively for the hCA XII).The kinetic data reported here strongly support compounds of this type for their future development as radiotracers in tumor pathologies which are strictly dependent on the enzymatic activity of the hCA IX and XII isoforms. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.03.054

文献信息

• Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII
  作者：Murat Bozdag、Ahmed Mahmoud Alafeefy、Abdul Malik Altamimi、Fabrizio Carta、Claudiu T. Supuran、Daniela Vullo

  DOI：10.1016/j.bmc.2017.03.054

  日期：2017.5

  We report a series of novel metanilamide-based derivatives 3a-q bearing the 2-mercapto-4-oxo-4H-quinazolin-3-yl moiety as tail. All compounds were synthesized by means of straightforward condensation procedures and were investigated in vitro for their inhibition potency against the human (h) carbonic anhydrase (CA; EC 4.2.1.1.1) isoforms I, II, IX and XII. Among all compounds tested the 6-iodo 3g and the 7-fluoro 3i derivatives were the most potent inhibitors against the tumor associated CA IX and XII isoform (K(1)s 1.5 and 2.7 nM respectively for the hCA IX and K1s 0.57 and 1.9 nM respectively for the hCA XII).The kinetic data reported here strongly support compounds of this type for their future development as radiotracers in tumor pathologies which are strictly dependent on the enzymatic activity of the hCA IX and XII isoforms. (C) 2017 Elsevier Ltd. All rights reserved.