4-[2-[3',6'-Bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]ethyl]benzenesulfonamide | 1333408-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-[2-[3',6'-Bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]ethyl]benzenesulfonamide
• CAS: 1333408-39-1
• 化学式: C₃₆H₄₀N₄O₄S
• 分子量: 624.804
• InChiKey: AXVQXDKRGPCGGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(9-(2-(chlorocarbonyl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-N-ethylethanaminium chloride 、 4-(2-氨乙基)苯磺酰胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 4-[2-[3',6'-Bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]ethyl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis of rhodamine B–benzenesulfonamide conjugates and their inhibitory activity against human α- and bacterial/fungal β-carbonic anhydrases

  摘要：

  A series of fluorescent sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors were obtained by attaching rhodamine B moieties to the scaffold of benzenesulfonamides. The new compounds have been investigated for the inhibition of 12 human alpha-CA isoforms (hCA I-hCA XIV), three bacterial and one fungal beta-class enzymes from the pathogens Mycobacterium tuberculosis and Candida albicans. All types of inhibitory activities have been detected, with several compounds showing low nanomolar inhibition against the transmembrane isoforms hCA IX, XII (cancer-associated) and XIV. The beta-CAs were inhibited in the micromolar range by these compounds which may have applications for the imaging of hypoxic tumors or bacteria due to their fluorescent moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.045

文献信息

• Synthesis of rhodamine B–benzenesulfonamide conjugates and their inhibitory activity against human α- and bacterial/fungal β-carbonic anhydrases
  作者：Marouan Rami、Alessio Innocenti、Jean-Louis Montero、Andrea Scozzafava、Jean-Yves Winum、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2011.07.045

  日期：2011.9

  A series of fluorescent sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors were obtained by attaching rhodamine B moieties to the scaffold of benzenesulfonamides. The new compounds have been investigated for the inhibition of 12 human alpha-CA isoforms (hCA I-hCA XIV), three bacterial and one fungal beta-class enzymes from the pathogens Mycobacterium tuberculosis and Candida albicans. All types of inhibitory activities have been detected, with several compounds showing low nanomolar inhibition against the transmembrane isoforms hCA IX, XII (cancer-associated) and XIV. The beta-CAs were inhibited in the micromolar range by these compounds which may have applications for the imaging of hypoxic tumors or bacteria due to their fluorescent moieties. (C) 2011 Elsevier Ltd. All rights reserved.