2-(4-methylphenylsulfonylimino)-2H-chromene-3-yl-methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside | 1619921-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(4-methylphenylsulfonylimino)-2H-chromene-3-yl-methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
• 英文别名: N-[3-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]chromen-2-ylidene]-4-methylbenzenesulfonamide
• CAS: 1619921-26-4
• 化学式: C₂₉H₃₅NO₁₄S
• 分子量: 653.661
• InChiKey: BUDRBKDVTWJHME-ZOGNILRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.83
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  238.17
• 氢给体数：
  7.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  2-(4-methylphenylsulfonylimino)-2H-chromene-3-yl-methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(14)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到2-(4-methylphenylsulfonylimino)-2H-chromene-3-yl-methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists

  摘要：

  A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4 N, -4C, -7, -8 N, -9 N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8 N, and 9 N with up to 40-fold affinity enhancements relative to methyl alpha-D-galactopyranoside due to the coumarylmethyl moieties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.063