4,4'-thiodipyridine-3-sulfonamide | 1078160-08-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,4'-thiodipyridine-3-sulfonamide
• 英文别名: 4,4'-Thiodi(pyridine-3-sulfonamide)；4-(3-sulfamoylpyridin-4-yl)sulfanylpyridine-3-sulfonamide
• CAS: 1078160-08-3
• 化学式: C₁₀H₁₀N₄O₄S₃
• 分子量: 346.412
• InChiKey: JYMNSJBFCKCLMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  188
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-巯基吡啶-3-磺酰胺 、 4-氯吡啶-3-磺酰胺 在 sodium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 61.0h， 以65%的产率得到4,4'-thiodipyridine-3-sulfonamide
  参考文献：
  名称：

  1,1-二氧吡啶并[4,3- e ] -1,4,2-二噻嗪-3-硫醇钾的合成及其在具有潜在生物活性的新型磺酰胺类化合物的合成中的应用

  摘要：

  1,1-二氧吡啶并[4,3- e ] -1,4,2-二噻嗪-3-硫醇钾2已经合成并用于7 H -1,1-二氧并吡啶[4,3- e ]的合成-1,4,2-二噻唑-3-硫醇盐3和3-甲基硫代吡啶并[4,3- e ] -1,4,2-二噻嗪1,1-二氧化物4可轻松获得其各种3-氨基衍生5-10。的肼解7,8和10，得到相应的3-氨基-2-（1,4-二氢-4- thioxopyrid -3-基磺酰基）胍11-13。随后12与4-氯苯甲醛反应，得到缩合产物14。1,4-二氢-2- thioxopyridine -3-磺酰胺15还从钾盐制备2在碱性水解，而15烷基化，得到适当š取代的衍生物16-19或S，N二取代的化合物20-21。

  DOI：

  10.1002/jhet.5570450525

文献信息

• Carbonic anhydrase inhibitors: Synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Franciszek Sączewski、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2010.02.020

  日期：2010.6

  A series of novel 4-substituted-3-pyridinesulfonamides (2-27 and 31-33) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 42 11), that is, the cytosolic, ubiquitous isozymes CA I and II, and transmembrane isozymes CA IX, XII (cancer-associated) and XIV. Against the human isozymes hCA I, the new compounds showed inhibition constants in the range of 0.078-11.7 mu M, against hCA II in the range of 9.9-140 nM, against hCA IX in the range of 4.6-313 nM, against hCA XII in the range of 3.4-21.6 nM, and against hCA XIV in the range of 50.9-160 nM, respectively. Compounds 4, 6, 7, 9, 11-14, 19, 20, 22-24, 26, 27, 31 and 32 showed excellent hCA IX inhibitory efficacy, with inhibition constants of 4.6-12 0 nM, being much more effective as compared to the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND 4-[N'-(6-Chloro-7-cyano-1,1-dioxo-1,4,2-benzodithiazin-3-yl)hydrazino]-3-pyridinesulfonamide (31) is the prominent of the compounds due to its remarkable inhibitory activity toward hCA I (K(I)s = 0.078 mu M), hCA IX (K(I)s = 7.2 nM) and hCA XII (K(I)s = 3.4 nM).