1-(3,4-dichlorophenacyl)-1,4-dihydro-4-oxo-3-pyridinesulfonamide | 1246373-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4-dichlorophenacyl)-1,4-dihydro-4-oxo-3-pyridinesulfonamide
• 英文别名: 1-[2-(3,4-dichlorophenyl)-2-oxoethyl]-4-oxopyridine-3-sulfonamide
• CAS: 1246373-44-3
• 化学式: C₁₃H₁₀Cl₂N₂O₄S
• 分子量: 361.205
• InChiKey: MDABKLUMWAFTGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-methoxy-3-pyridinesulfonamide 、 2-溴-3',4'-二氯苯乙酮 以 乙腈 为溶剂， 反应 72.0h， 以95%的产率得到1-(3,4-dichlorophenacyl)-1,4-dihydro-4-oxo-3-pyridinesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Regioselective synthesis of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII

  摘要：

  A series of 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamide (2-16) have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is the cytosolic ubiquitous CA I and II, and cancer-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed inhibition constants in the range of 1.09-12.1 mu M, against hCA II in the range of 50.5-172 nM, against hCA IX in the range of 5.2-118 nM, and against hCA XII in the range of 8.7-381 nM, respectively. Compounds 2, 3, 5-9, 11, 13 and 14 showed excellent hCA IX inhibitory efficacy, with K(I)s = 5.2-11.0 nM, being much more effective as compared to the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). Compounds 2, 3, 5-9, 11 and 13 were also very effective hCA XII inhibitors (K(I)s = 8.7-45.2 nM) which are comparable or more effective than those clinically used EZA and DCP (K(I)s = 22 and 50 nM), respectively. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.011

文献信息

• Carbonic anhydrase inhibitors. Regioselective synthesis of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2010.05.011

  日期：2010.9

  A series of 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamide (2-16) have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is the cytosolic ubiquitous CA I and II, and cancer-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed inhibition constants in the range of 1.09-12.1 mu M, against hCA II in the range of 50.5-172 nM, against hCA IX in the range of 5.2-118 nM, and against hCA XII in the range of 8.7-381 nM, respectively. Compounds 2, 3, 5-9, 11, 13 and 14 showed excellent hCA IX inhibitory efficacy, with K(I)s = 5.2-11.0 nM, being much more effective as compared to the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). Compounds 2, 3, 5-9, 11 and 13 were also very effective hCA XII inhibitors (K(I)s = 8.7-45.2 nM) which are comparable or more effective than those clinically used EZA and DCP (K(I)s = 22 and 50 nM), respectively. (C) 2010 Elsevier Masson SAS. All rights reserved.