4-methyl-1-(3-sulfamoylpyrid-4-yl)pyridinium chloride | 1335122-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-methyl-1-(3-sulfamoylpyrid-4-yl)pyridinium chloride
• 英文别名: 4-(4-Methylpyridin-1-ium-1-yl)pyridine-3-sulfonamide;chloride
• CAS: 1335122-14-9
• 化学式: C₁₁H₁₂N₃O₂S*Cl
• 分子量: 285.754
• InChiKey: LLNVCJYNVGOBTC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.68
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-1-(3-sulfamoylpyrid-4-yl)pyridinium chloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以60%的产率得到8-methyl-6,6a-dihydrodipyrido[2,1-c:4',3'-e][1,2,4]thiadiazine 5,5-dioxide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Synthesis, molecular structures, and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with novel 3-pyridinesulfonamide derivatives

  摘要：

  A series of novel 3-pyridinesulfonamide derivatives (2-5, 9-11 and 13-15) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is, the cytosolic ubiquitous CA I and II, and isozymes CA IX and XII (cancer-associated), and XIV. Against the human isozyme hCA I the new compounds showed K(I)s in the range of 0.089-251 mu M, whereas toward hCA II, K(I)s = 50.5-487 nM. Isozyme hCA IX was inhibited with K(I)s in the range of 5.2-18.3 nM, while hCA XII with K(I)s = 6.0-16.4 nM, and hCA XIV with K(I)s = 76.4-152.0 nM. All of the new compounds 2-5,9-11 and 13-15 showed excellent hCA IX inhibitory efficacy, with Kis = 5.2-18.3 nM, being much more effective as compared to the clinically used AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.011
• 作为产物：
  描述：

  4-甲基吡啶 、 4-氯吡啶-3-磺酰胺 以 乙腈 为溶剂， 反应 18.0h， 以93%的产率得到4-methyl-1-(3-sulfamoylpyrid-4-yl)pyridinium chloride
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Synthesis, molecular structures, and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with novel 3-pyridinesulfonamide derivatives

  摘要：

  A series of novel 3-pyridinesulfonamide derivatives (2-5, 9-11 and 13-15) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is, the cytosolic ubiquitous CA I and II, and isozymes CA IX and XII (cancer-associated), and XIV. Against the human isozyme hCA I the new compounds showed K(I)s in the range of 0.089-251 mu M, whereas toward hCA II, K(I)s = 50.5-487 nM. Isozyme hCA IX was inhibited with K(I)s in the range of 5.2-18.3 nM, while hCA XII with K(I)s = 6.0-16.4 nM, and hCA XIV with K(I)s = 76.4-152.0 nM. All of the new compounds 2-5,9-11 and 13-15 showed excellent hCA IX inhibitory efficacy, with Kis = 5.2-18.3 nM, being much more effective as compared to the clinically used AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.011

文献信息

• Carbonic anhydrase inhibitors. Synthesis, molecular structures, and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with novel 3-pyridinesulfonamide derivatives
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Maria Gdaniec、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2011.07.011

  日期：2011.9

  A series of novel 3-pyridinesulfonamide derivatives (2-5, 9-11 and 13-15) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is, the cytosolic ubiquitous CA I and II, and isozymes CA IX and XII (cancer-associated), and XIV. Against the human isozyme hCA I the new compounds showed K(I)s in the range of 0.089-251 mu M, whereas toward hCA II, K(I)s = 50.5-487 nM. Isozyme hCA IX was inhibited with K(I)s in the range of 5.2-18.3 nM, while hCA XII with K(I)s = 6.0-16.4 nM, and hCA XIV with K(I)s = 76.4-152.0 nM. All of the new compounds 2-5,9-11 and 13-15 showed excellent hCA IX inhibitory efficacy, with Kis = 5.2-18.3 nM, being much more effective as compared to the clinically used AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.