5-[p-(aminosulfonyl)phenyl]-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazole | 1338457-64-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-[p-(aminosulfonyl)phenyl]-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazole
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[5-(4-sulfamoylphenyl)triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 1338457-64-9
• 化学式: C₂₂H₂₆N₄O₁₁S
• 分子量: 554.535
• InChiKey: KYLWRZNUXUAUBH-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  214
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5-[p-(aminosulfonyl)phenyl]-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazole 在 甲醇 、 sodium methylate 作用下， 反应 16.5h， 以88%的产率得到5-[p-(aminosulfonyl)phenyl]-1-(β-D-glucopyranosyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of glycoconjugate carbonic anhydrase inhibitors by ruthenium-catalysed azide-alkyne 1,3-dipolar cycloaddition

  摘要：

  Carbonic anhydrase IX (CA IX) is a recently validated target for the development of new cancer therapies. In this Letter we describe the synthesis and CA inhibition of a novel series of carbohydrate-based 1, 5-disubstituted-1,2,3-triazole benzenesulfonamides. The key step of our synthesis is the regioselective Huisgen's 1,3-dipolar cycloaddition reaction (1,3-DCR) from carbohydrate azide substrates and 4-ethynylbenzenesulfonamide using a ruthenium-catalysed azide-alkyne cycloaddition (RuAAC). Our findings identified a number of triazole inhibitors (compounds 18, 19, 21-23, and 26) that block CA IX activity with inhibition constants less than 10 nM. One inhibitor (compound 17) possessed very good selectivity for CA IX over off-target CAs. These CA inhibitors have developmental potential to selectively target cancer cells, leading to cell death. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.066
• 作为产物：
  描述：

  1-乙炔-4-(甲基磺酰基)-苯 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以43%的产率得到5-[p-(aminosulfonyl)phenyl]-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of glycoconjugate carbonic anhydrase inhibitors by ruthenium-catalysed azide-alkyne 1,3-dipolar cycloaddition

  摘要：

  Carbonic anhydrase IX (CA IX) is a recently validated target for the development of new cancer therapies. In this Letter we describe the synthesis and CA inhibition of a novel series of carbohydrate-based 1, 5-disubstituted-1,2,3-triazole benzenesulfonamides. The key step of our synthesis is the regioselective Huisgen's 1,3-dipolar cycloaddition reaction (1,3-DCR) from carbohydrate azide substrates and 4-ethynylbenzenesulfonamide using a ruthenium-catalysed azide-alkyne cycloaddition (RuAAC). Our findings identified a number of triazole inhibitors (compounds 18, 19, 21-23, and 26) that block CA IX activity with inhibition constants less than 10 nM. One inhibitor (compound 17) possessed very good selectivity for CA IX over off-target CAs. These CA inhibitors have developmental potential to selectively target cancer cells, leading to cell death. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.066