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

• 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-mannopyranosylamine
• 英文别名: N-(p-sulfamoylphenyl)mannopyranosylamine；4-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-ylamino)benzenesulfonamide；4-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]benzenesulfonamide
• 化学式: C₁₂H₁₈N₂O₇S
• 分子量: 334.35
• InChiKey: RMCYKIOWPVOBJX-LDMBFOFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  171
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  D-甘露糖 、 磺胺 在 ammonium chloride 作用下， 以 乙醇 为溶剂， 生成 N-(p-sulfamoylphenyl)-β-D-mannopyranosylamine
  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

• Molecular and crystal structures of N-arylglycopyranosylamines formed by reaction between sulfanilamide and d-ribose, d-arabinose and d-mannose
  作者：Charles R. Ojala、Joanne M. Ostman、William H. Ojala、Summer E. Hanson

  DOI：10.1016/s0008-6215(01)00011-8

  日期：2001.4

  conformation at the monosaccharide ring and the gt conformation at the C-6-O-6 side chain. Occupancy of the water molecule in the crystal of 3 actually examined was 22%. The degree of interaction between sulfamoyl groups and monosaccharide moieties varies from structure to structure. The packing arrangement of 2 involves hydrogen bonding between sulfamoyl groups and monosaccharide hydroxyl groups, but interactions

  已经确定了通过磺酰胺与D-核糖，D-阿拉伯糖和D-甘露糖反应制备的三种单糖衍生物的X射线晶体结构。衍生物是N-（对氨基磺酰基苯基）-α-D-核糖吡喃糖胺（1），N-（对氨基磺酰基苯基）-N-D-阿拉伯吡喃糖胺（2）和N-（对氨基磺酰基苯基）-β-D-甘露吡喃糖胺一水合物（3）。1和2的单糖环具有1C4构象，并通过0-2至0-4的分子内氢键稳定在1中。化合物3在单糖环上具有4C1构象，在C-6-O-6侧链上具有gt构象。实际检查的3个晶体中水分子的占有率为22％。氨磺酰基与单糖部分之间的相互作用程度因结构而异。2的堆积结构涉及氨磺酰基和单糖羟基之间的氢键，但是这种类型的相互作用在1中较少，而在3中，氢键严格地在单糖羟基之间或在氨磺酰基之间。成对的氢键（两点接触）将所有三个结构中的相邻分子连接在一起，在1和2中的螺杆轴向相关分子之间，以及在3中的翻译相关分子之间。3中的接触由O-3-H定义。在
• 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.