2,4,6-Trifluorophenyl sulfamate | 1186393-82-7

• 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: 2,4,6-Trifluorophenyl sulfamate
• 英文别名: (2,4,6-trifluorophenyl) sulfamate
• CAS: 1186393-82-7
• 化学式: C₆H₄F₃NO₃S
• 分子量: 227.164
• InChiKey: TVQKGOMPDMZMBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4,6-三氟苯酚 在 氨基磺酰氯 作用下， 以 2,4-滴二甲胺盐 为溶剂， 生成 2,4,6-Trifluorophenyl sulfamate
  参考文献：
  名称：

  Carbonic anhydrase inhibitors; Fluorinated phenyl sulfamates show strong inhibitory activity and selectivity for the inhibition of the tumor-associated isozymes IX and XII over the cytosolic ones I and II

  摘要：

  A series of fluorinated-phenylsulfamates have been prepared by sulfamoylation of the corresponding phenols and the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isozymes, the cytosolic CA I and II (off-targets), and the transmembrane, tumor-associated CA IX and XII is investigated. Unlike the lead molecule (phenylsulfamate), a very potent CA I and II inhibitor and a modest CA IX/XII inhibitor, the fluorinated sulfamates were stronger inhibitors of CA IX (K(I)s of 2.8-47 nM) and CA XII (K(I)s of 1.9-35 nM) than of CA I (K(I)s of 53-415 nM) and CA II (K(I)s of 20-113 nM). Some of these compounds were selective CA IX over CA II inhibitors, with selectivity ratios in the range of 11.4-12.1, making them interesting candidates for targeting hypoxic tumors overexpressing CA IX and/or XII. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.056

文献信息

• Carbonic anhydrase inhibitors; Fluorinated phenyl sulfamates show strong inhibitory activity and selectivity for the inhibition of the tumor-associated isozymes IX and XII over the cytosolic ones I and II
  作者：Jean-Yves Winum、Alessio Innocenti、Daniela Vullo、Jean-Louis Montero、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2009.07.056

  日期：2009.9

  A series of fluorinated-phenylsulfamates have been prepared by sulfamoylation of the corresponding phenols and the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isozymes, the cytosolic CA I and II (off-targets), and the transmembrane, tumor-associated CA IX and XII is investigated. Unlike the lead molecule (phenylsulfamate), a very potent CA I and II inhibitor and a modest CA IX/XII inhibitor, the fluorinated sulfamates were stronger inhibitors of CA IX (K(I)s of 2.8-47 nM) and CA XII (K(I)s of 1.9-35 nM) than of CA I (K(I)s of 53-415 nM) and CA II (K(I)s of 20-113 nM). Some of these compounds were selective CA IX over CA II inhibitors, with selectivity ratios in the range of 11.4-12.1, making them interesting candidates for targeting hypoxic tumors overexpressing CA IX and/or XII. (C) 2009 Elsevier Ltd. All rights reserved.