2,4,6-Trimethyl-1-(4-sulfamoyl-phenyl)-pyridinium; perchlorate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-Trimethyl-1-(4-sulfamoyl-phenyl)-pyridinium; perchlorate
• 英文别名: 1-[4-(Aminosulfonyl)phenyl]-2,4,6-trimethyl-pyridinium perchorate；4-(2,4,6-trimethylpyridin-1-ium-1-yl)benzenesulfonamide;perchlorate
• 化学式: C₁₄H₁₇N₂O₂S*ClO₄
• 分子量: 376.818
• InChiKey: AJBZTFFKRXFWJS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.22
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4,6-三甲基吡喃鎓高氯酸盐 、 磺胺 在 乙酸酐 、 溶剂黄146 、 三乙胺 作用下， 生成 2,4,6-Trimethyl-1-(4-sulfamoyl-phenyl)-pyridinium; perchlorate
  参考文献：
  名称：

  Carbonic anhydrase inhibitors — Part 53. Synthesis of substituted-pyridinium derivatives of aromatic sulfonamides: The first non-polymeric membrane-impermeable inhibitors with selectivity for isozyme IV

  摘要：

  Reaction of three aromatic sulfonamides containing a free amino group, i.e., sulfanilamide, homosulfanilamide and 4-(2-aminoethyl)-benzenesulfonamide with di-, tri- or tetra-substituted pyrylium salts afforded three series of cationic sulfonamides, containing a large variety of moieties substituting the pyridinium ring. The new derivatives were assayed as inhibitors of three carbonic anhydrase (CA) isozymes, CA I, II (cytosolic forms) and IV (membrane-bound form). Efficient inhibition was observed against all three isozymes, but due to the cationic nature of these inhibitors, in vivo and ex vivo experiments showed that only CA IV is selectively inhibited to a high degree, without affecting the cytosolic isozymes, present in appreciable concentrations in the experimental model used. This is the first example of selective in vivo inhibition of only one physiologically relevant CA isozyme with non-polymeric inhibitors and might lead to more selective drugs from this class of pharmacological agents. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80017-2

文献信息

• Antimicrobial and antiviral activity of pyridinium salts
  作者：G. N. Dorofeenko、E. I. Sadekova、G. A. Korol'chenko、V. I. Votyakov、M. M. Timofeeva、I. V. Bruskova、L. F. Laguta、V. Ya. Klimovich、Yu. N. Simkina、M. N. Shashikhina

  DOI：10.1007/bf00773087

  日期：1982.8