1,4-dihydro-1-(2,4-dinitrophenyl)-4-oxo-3-pyridinesulfonamide | 1246373-48-7

• 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: 1,4-dihydro-1-(2,4-dinitrophenyl)-4-oxo-3-pyridinesulfonamide
• 英文别名: 1-(2,4-dinitrophenyl)-4-oxopyridine-3-sulfonamide
• CAS: 1246373-48-7
• 化学式: C₁₁H₈N₄O₇S
• 分子量: 340.273
• InChiKey: GEDYQQXTTMSJSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  181
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-methoxy-3-pyridinesulfonamide 、 1-氯-2,4-二硝基苯 以 乙腈 为溶剂， 反应 56.0h， 以71%的产率得到1,4-dihydro-1-(2,4-dinitrophenyl)-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

• On the Reaction Products of 4-Substituted 3-Pyridinesulfonamides with Some Benzenesulfonyl Chloride Derivatives
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Krzysztof Szafrański

  DOI：10.1002/jhet.1013

  日期：2014.1

  The reactions of 4‐substituted 3‐pyridinesulfonamides 1a, 1b, 1c, 1d, 1e with benzenesulfonyl chlorides 2a, 2b, 2c, 2d, 2e, 2f in acetonitrile were investigated. Depending on the structure of arylsulfonyl chlorides and the reaction conditions the following four types of products were obtained in good yields: 3‐sulfamoyl‐4‐R‐1‐arylpyridinium chlorides 3, 4, 5, 6, 7, 8; 1,10‐bis(3‐nitrobenzenesulfonylimino)deca‐2

  研究了4-取代的3-吡啶磺酰胺1a，1b，1c，1d，1e与苯磺酰氯2a，2b，2c，2d，2e，2f在乙腈中的反应。取决于芳基磺酰氯和以良好的收率得到了以下四种类型的产品的反应条件的结构：3-氨磺酰基- 4- [R -1- arylpyridinium氯化物3，4，5，6，7，8; 1,10-双（3- nitrobenzenesulfonylimino）癸-2,4,6,8-四烯-2,9- disulfonamides 9，10，11，12 ; 1-取代的1,4-二氢-4-氧代-3- pyridinesulfonamides 13，14 ; 和4-甲氧基-3- [ N-（2,5-二氯苯基）磺酰基]磺酰胺化物15和16。讨论了这些反应的机理。
• 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.