(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-sulfamoyltetrahydro-2H-pyran-2-carboxylic acid | 1138026-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-sulfamoyltetrahydro-2H-pyran-2-carboxylic acid
• 英文别名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-sulfamoyloxane-2-carboxylic acid
• CAS: 1138026-37-5
• 化学式: C₆H₁₁NO₈S
• 分子量: 257.221
• InChiKey: FCQDJTXNFBKMBE-WAXACMCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  176
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranuronylsulfonamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-sulfamoyltetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  S-Glycosyl Primary Sulfonamides−A New Structural Class for Selective Inhibition of Cancer-Associated Carbonic Anhydrases

  摘要：

  In this paper, we present. a. new class of carbonic anhydrase (CA) inhibitor that was designed to selectively target the extracellular domains of the cancer-relevant CA isozymes. The aromatic moiety of the classical zinc binding sulfonamide CA inhibitors is absent from these compounds and instead they incorporate a hydrophilic mono- or disaccharide fragment directly attached to the sulfonamide group to give S-glycosyl primary sulfonamides (1-10). The inhibition properties of these compounds at the physiologically abundant human CA isozymes I and II and cancer-associated IX and XII were determined, and all compounds had moderate potency with KiS in the micromolar range. We present the crystal structures of anomeric sulfonamides 4, 7, and 10 and the sugar sulfamate drug topiramate in complex with human recombinant CA II. From these structures, we have obtained valuable insights into ligand-protein interactions of these novel carb ohydrate-based sulfonamides with CA.

  DOI：

  10.1021/jm900914e