N-(p-sulfamoylphenyl)-β-D-arabinopyranosylamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(p-sulfamoylphenyl)-β-D-arabinopyranosylamine
• 英文别名: 4-((2R,3S,4R,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-ylamino)benzenesulfonamide；4-[[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]amino]benzenesulfonamide
• 化学式: C₁₁H₁₆N₂O₆S
• 分子量: 304.324
• InChiKey: FGIKBEHQPSXRFZ-CHWFTXMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  阿拉伯糖 、 磺胺 在 ammonium chloride 作用下， 以 乙醇 为溶剂， 生成 N-(p-sulfamoylphenyl)-β-D-arabinopyranosylamine
  参考文献：
  名称：

  Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-α-d-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits

  摘要：

  A series of N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines was prepared by reaction of sulfanilamide with different monosaccharides in the presence of ammonium chloride. The new compounds were investigated for inhibition of the metalloenzyme carbonic anhydrase (CA, EC 4.2. 1.1), involved in aqueous humor secretion within the mammalian eye. Isozymes CA I and CA II were strongly inhibited by some of these compounds, which showed inhibition constants in the range of 510-1200 nM against CA I and 10-25 nM against CA II, similarly to clinically used sulfonamides, such as acetazolamide, methazolamide, dichlorophenamide, dorzolamide and brinzolamide. The presence of sugar moieties in these molecules induced an enhanced water solubility as compared to other sulfonamides. In hypertensive rabbits (a widely used animal model of glaucoma), two of the new compounds showed strong and long-lasting intraocular pressure (IOP) lowering, being more effective than dorzolamide and brinzolamide, the two clinically used, topically acting antiglaucoma sulfonamides with CA inhibitory properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.063

文献信息

• Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-α-d-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits
  作者：Jean-Yves Winum、Angela Casini、Francesco Mincione、Michele Starnotti、Jean-Louis Montero、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2003.09.063

  日期：2004.1

  A series of N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines was prepared by reaction of sulfanilamide with different monosaccharides in the presence of ammonium chloride. The new compounds were investigated for inhibition of the metalloenzyme carbonic anhydrase (CA, EC 4.2. 1.1), involved in aqueous humor secretion within the mammalian eye. Isozymes CA I and CA II were strongly inhibited by some of these compounds, which showed inhibition constants in the range of 510-1200 nM against CA I and 10-25 nM against CA II, similarly to clinically used sulfonamides, such as acetazolamide, methazolamide, dichlorophenamide, dorzolamide and brinzolamide. The presence of sugar moieties in these molecules induced an enhanced water solubility as compared to other sulfonamides. In hypertensive rabbits (a widely used animal model of glaucoma), two of the new compounds showed strong and long-lasting intraocular pressure (IOP) lowering, being more effective than dorzolamide and brinzolamide, the two clinically used, topically acting antiglaucoma sulfonamides with CA inhibitory properties. (C) 2003 Elsevier Ltd. All rights reserved.