N²,N⁶-bis(4-sulfamoylphenyl)pyridine-2,6-dicarboxamide

• 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: N²,N⁶-bis(4-sulfamoylphenyl)pyridine-2,6-dicarboxamide
• 英文别名: n2,n6-Bis(4-sulfamoylphenyl)pyridine-2,6-dicarboxamide；2-N,6-N-bis(4-sulfamoylphenyl)pyridine-2,6-dicarboxamide
• 化学式: C₁₉H₁₇N₅O₆S₂
• 分子量: 475.506
• InChiKey: SDSRWHJMSJVLJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  208
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,6-氯甲酰吡啶 、 磺胺 以 二氯甲烷 、 丙酮 为溶剂， 反应 12.0h， 以76%的产率得到N²,N⁶-bis(4-sulfamoylphenyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Synthesis and Enzyme Inhibitory Activity of Novel Pyridine-2,6-dicarboxamides Bearing Primary Sulfonamide Groups

  摘要：

  New pyridine-2,6-dicarboxamide derivatives containing sulfonamide groups were synthesized by the coupling of pyridine-2,6-dicarbonyl dichloride and various aminobenzenesulfonamides in a mixture of dichloromethane and acetone. The pyridinedicarboxamide-based sulfonamides were evaluated as carbonic anhydrase (CA) and cholinesterase (ChE) inhibitors, and they showed IC50 values in the ranges 12.8-37.6 nM against human carbonic anhydrase I (hCA I), 17.8-46.7 nM against human carbonic anhydrase II (hCA II), 98.4-197.5 nM against acetylcholinesterase (AChE), and 82.2-172.7 nM against butyrylcholinesterase (BuChE). These results are comparable with those for known inhibitors such as acetazolamide (IC50 = 32.1 nM for hCA I and IC50 = 51.0 nM for hCA II) and rivastigmine (IC50 = 60.2 nM for AChE and IC50 = 14.0 nM for BuChE), which qualifies the synthesized compounds as candidates for a more in-depth study.

  DOI：

  10.1134/s1070428019120248

文献信息

• Synthesis and Enzyme Inhibitory Activity of Novel Pyridine-2,6-dicarboxamides Bearing Primary Sulfonamide Groups
  作者：N. Stellenboom、A. R. Baykan

  DOI：10.1134/s1070428019120248

  日期：2019.12

  New pyridine-2,6-dicarboxamide derivatives containing sulfonamide groups were synthesized by the coupling of pyridine-2,6-dicarbonyl dichloride and various aminobenzenesulfonamides in a mixture of dichloromethane and acetone. The pyridinedicarboxamide-based sulfonamides were evaluated as carbonic anhydrase (CA) and cholinesterase (ChE) inhibitors, and they showed IC50 values in the ranges 12.8-37.6 nM against human carbonic anhydrase I (hCA I), 17.8-46.7 nM against human carbonic anhydrase II (hCA II), 98.4-197.5 nM against acetylcholinesterase (AChE), and 82.2-172.7 nM against butyrylcholinesterase (BuChE). These results are comparable with those for known inhibitors such as acetazolamide (IC50 = 32.1 nM for hCA I and IC50 = 51.0 nM for hCA II) and rivastigmine (IC50 = 60.2 nM for AChE and IC50 = 14.0 nM for BuChE), which qualifies the synthesized compounds as candidates for a more in-depth study.