4-(4-{(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide | 935678-27-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-{(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide
• 英文别名: Glycoconjugate sulfonamide 10；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[[1-(4-sulfamoylphenyl)triazol-4-yl]methoxy]oxolan-2-yl]methyl benzoate
• CAS: 935678-27-6
• 化学式: C₃₅H₃₀N₄O₁₀S
• 分子量: 698.71
• InChiKey: GTFXZZCYZNZBPR-VLMNPVQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  197
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-(4-{(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到4-[4-({[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-1H-1,2,3-triazol-1-yl]benzene-1-sulfonamide
  参考文献：
  名称：

  Carbonic Anhydrase Inhibitors:  Inhibition of Isozymes I, II, and IX with Triazole-Linked O-Glycosides of Benzene Sulfonamides

  摘要：

  We report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low-nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 and 9.7-107 nM, respectively, was observed. The most potent inhibitor against hCA IX was the galactose derivative 8 (K-i = 9.7 nM); this is so far the most potent glycoconjugate inhibitor reported for the tumor-associated hCA IX. These carbohydrate-tethered sulfonamides may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly.

  DOI：

  10.1021/jm061320h
• 作为产物：
  描述：

  1-O-propynyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 、 4-azidobenzenesulfonamide 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 叔丁醇 为溶剂， 以91%的产率得到4-(4-{(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Carbonic Anhydrase Inhibitors:  Inhibition of Isozymes I, II, and IX with Triazole-Linked O-Glycosides of Benzene Sulfonamides

  摘要：

  We report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low-nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 and 9.7-107 nM, respectively, was observed. The most potent inhibitor against hCA IX was the galactose derivative 8 (K-i = 9.7 nM); this is so far the most potent glycoconjugate inhibitor reported for the tumor-associated hCA IX. These carbohydrate-tethered sulfonamides may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly.

  DOI：

  10.1021/jm061320h