4-(4-benzylpiperazin-1-yl)-3-pyridinesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(4-benzylpiperazin-1-yl)-3-pyridinesulfonamide
• 英文别名: 4-(4-Benzylpiperazin-1-yl)pyridine-3-sulfonamide；4-(4-benzylpiperazin-1-yl)pyridine-3-sulfonamide
• 化学式: C₁₆H₂₀N₄O₂S
• 分子量: 332.426
• InChiKey: OJRDPGPSJAPOJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-苄基哌嗪 、 4-氯吡啶-3-磺酰胺 以 甲醇 为溶剂， 反应 48.0h， 以57%的产率得到4-(4-benzylpiperazin-1-yl)-3-pyridinesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Synthesis of heterocyclic 4-substituted pyridine-3-sulfonamide derivatives and their inhibition of the human cytosolic isozymes I and II and transmembrane tumor-associated isozymes IX and XII

  摘要：

  A series of novel heterocyclic 4-substituted pyridine-3-sulfonamides 2-13,15-20 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC4.2.1.1), that is the cytosolic CA I and II, and tumor-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed K-I values in the range 169-5400 nM, toward hCA II in range 58.5-1238 nM, against hCA IX in range 19.5-652 nM and against hCA XII in the range of 16.8-768 nM. Compounds 15-19 representing 4-(1H-pyrazol-1-yl)-3-pyridinesulfonamide derivatives showed good hCA IX inhibitory efficacy with K-I = 19.5-48.6 nM comparable or more effective than clinically used sulfonamides: AAZ, MZA, EZA, DCP, IND (K-I = 24-50 nM). Anticancer evaluation at a single dose 10 mu M, against a panel of 60 human tumor cell lines, was performed at the US National Cancer Institute, on compounds 2, 3, 5-13, 16,17, 19, 20. Among them 6 bearing 4-(3,4,-dichlorophenyl)piperazine moiety showed broad spectrum of growth inhibition in the range 25-89% over 26 cell lines representing all tumors subpanels. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.027

文献信息

• Carbonic anhydrase inhibitors. Synthesis of heterocyclic 4-substituted pyridine-3-sulfonamide derivatives and their inhibition of the human cytosolic isozymes I and II and transmembrane tumor-associated isozymes IX and XII
  作者：Jarosław Sławiński、Krzysztof Szafrański、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2013.09.027

  日期：2013.11

  A series of novel heterocyclic 4-substituted pyridine-3-sulfonamides 2-13,15-20 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC4.2.1.1), that is the cytosolic CA I and II, and tumor-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed K-I values in the range 169-5400 nM, toward hCA II in range 58.5-1238 nM, against hCA IX in range 19.5-652 nM and against hCA XII in the range of 16.8-768 nM. Compounds 15-19 representing 4-(1H-pyrazol-1-yl)-3-pyridinesulfonamide derivatives showed good hCA IX inhibitory efficacy with K-I = 19.5-48.6 nM comparable or more effective than clinically used sulfonamides: AAZ, MZA, EZA, DCP, IND (K-I = 24-50 nM). Anticancer evaluation at a single dose 10 mu M, against a panel of 60 human tumor cell lines, was performed at the US National Cancer Institute, on compounds 2, 3, 5-13, 16,17, 19, 20. Among them 6 bearing 4-(3,4,-dichlorophenyl)piperazine moiety showed broad spectrum of growth inhibition in the range 25-89% over 26 cell lines representing all tumors subpanels. (C) 2013 Elsevier Masson SAS. All rights reserved.