4-[2-(4-sulfamoylphenyl)ethylamino]-3-pyridinesulfonamide | 1229666-36-7

• 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: 4-[2-(4-sulfamoylphenyl)ethylamino]-3-pyridinesulfonamide
• 英文别名: 4-[2-(4-sulfamoylphenyl)ethylamino]-3-pyridinosulfonamide；4-[2-(4-sulfamoylphenyl)ethylamino]pyridine-3-sulfonamide
• CAS: 1229666-36-7
• 化学式: C₁₃H₁₆N₄O₄S₂
• 分子量: 356.426
• InChiKey: NSQHBCSUZOLMBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[2-(4-sulfamoylphenyl)ethylamino]-3-pyridinesulfonamide 、 碘甲烷 以 乙腈 为溶剂， 反应 98.0h， 以93.6%的产率得到3-sulfamoyl-4-[2-(4-sulfamoylphenyl)ethylamino]-1-methylpyridinium iodide
  参考文献：
  名称：

  Synthesis of a new series of N4-substituted 4-(2-aminoethyl)benzenesulfonamides and their inhibitory effect on human carbonic anhydrase cytosolic isozymes I and II and transmembrane tumor-associated isozymes IX and XII

  摘要：

  A series of novel N(4)-substituted 4-(2-aminoethyl)benzenesulfonamides 5-17 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 CA I and II, and tumor-associated isozymes CA IX and XII. Against the human CA I investigated compounds displayed KI values from 96.3 to 3520 nM, toward hCA II at range of 18.1-2055 nM, while against hCA IX ranging from 5.9 to 419 nM and against hCA XII in the range of 4.0-414 nM. The very good inhibitory activity against tumor-associated hCA IX and hCA XII was found. The six new compounds displayed a powerful inhibitory potency toward hCA IX (K(I) = 5.9-10.7 nM) in comparison with the clinically used CAIs AAZ, MZA, EZA, DCP and IND (24-50 nM). The most potent hCA IX and hCA XII inhibitors 11 and 12 (K(I): 5.9 and 6.2 nM for hCA IX and 4.3 and 4.0 nM for hCA XII, respectively) belonged to the compounds with cationic character and presented meaningful affinity to the transmembrane isoforms hCA IX and XII than to physiologically dominant isozymes hCA I and II with the selectivity ratios hCA IX versus hCA II and hCA XII versus hCA II for 11 and 12 in the range of 10-15.

  DOI：

  10.1016/j.ejmech.2014.06.074
• 作为产物：
  描述：

  4-氯吡啶-3-磺酰胺 、 4-(2-氨乙基)苯磺酰胺 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以73%的产率得到4-[2-(4-sulfamoylphenyl)ethylamino]-3-pyridinesulfonamide
  参考文献：
  名称：

  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

  摘要：

  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).

  DOI：

  10.1016/j.ejmech.2010.02.020