(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-sulfonamide | 1138026-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-sulfonamide
• 英文别名: (2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-sulfonamide
• CAS: 1138026-38-6
• 化学式: C₁₂H₂₃NO₁₂S
• 分子量: 405.38
• InChiKey: DDOHHRUODNXYAC-XLOQQCSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  238
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  (1s)-2,3,6-Tri-O-Acetyl-1,5-Anhydro-1-Sulfamoyl-4-O-(2,3,4,6-Tetra-O-Acetyl-Beta-D-Galactopyranosyl)-D-Glucitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以55%的产率得到(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-sulfonamide
  参考文献：
  名称：

  Synthesis of S-Glycosyl Primary Sulfonamides

  摘要：

  The synthesis of S-glycosyl sulfonamides wherein the primary sulfonamide functional group (-SO2NH2) is directly attached to the anomeric position of a carbohydrate moiety is reported. Our general approach consists of first introducing a thioacetate group at die anomeric center of a per-O-acetylated sugar derivative. From this follows formation of a glycosyl sulfenamide (sugar-SNR2), oxidation of the sulfenamide to give a glycosyl N-protected sulfonamide (sugar-SO2NR2), and removal of the sulfonamide protecting (R) group to yield a primary sulfonamide at the anomeric center (sugar-SO2NH2). A variety of mono- and disaccharide derivatives were synthesized using this new methodology.

  DOI：

  10.1021/jo9000367

文献信息

• <i>S</i>-Glycosyl Primary Sulfonamides−A New Structural Class for Selective Inhibition of Cancer-Associated Carbonic Anhydrases
  作者：Marie Lopez、Blessy Paul、Andreas Hofmann、Julia Morizzi、Quoc K. Wu、Susan A. Charman、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm900914e

  日期：2009.10.22

  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.