4-({[4-(aminosulfonyl)benzoyl]amino}methyl)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1H-1,2,3-triazole | 915694-60-9

• 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: 4-({[4-(aminosulfonyl)benzoyl]amino}methyl)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1H-1,2,3-triazole
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(4-{[(4-sulfamoylphenyl)formamido]methyl}-1H-1,2,3-triazol-1-yl)oxan-2-yl]methyl acetate；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-[[(4-sulfamoylbenzoyl)amino]methyl]triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 915694-60-9
• 化学式: C₂₄H₂₉N₅O₁₂S
• 分子量: 611.587
• InChiKey: RZDXNLXHFKCYHA-KQWJERSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  243
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4-({[4-(aminosulfonyl)benzoyl]amino}methyl)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1H-1,2,3-triazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到4-(4-sulfamoylbenzamido)methyl-1-(β-D-galactopyranosyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  A Novel Class of Carbonic Anhydrase Inhibitors:  Glycoconjugate Benzene Sulfonamides Prepared by “Click-Tailing”

  摘要：

  Aryl and heteroaryl sulfonamides (ArSO2NH2) are therapeutically used to inhibit the catalytic activity of carbonic anhydrases (CAs). Using a "click- tail" approach a novel class of glycoconjugate benzene sulfonamides have been synthesized that contain diverse carbohydrate- triazole tails. These compounds were assessed for their ability to inhibit three human CA isozymes in vitro: cytosolic hCA I and hCA II and transmembrane, tumor- associated hCA IX. This isozyme has a minimal expression in normal tissue but is overexpressed in hypoxic tumors and its inhibition is a current approach toward new cancer therapies. The qualitative structure- activity for all derivatives demonstrated that the stereochemical diversity present within the carbohydrate tails effectively interrogated the CA active site topology, to generate several inhibitors that were potent and selective toward hCA IX, an important outcome in the quest for potential cancer therapy applications based on CA inhibition.

  DOI：

  10.1021/jm060967z
• 作为产物：
  描述：

  对羧基苯磺酰胺 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 6.0h， 生成 4-({[4-(aminosulfonyl)benzoyl]amino}methyl)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  A Novel Class of Carbonic Anhydrase Inhibitors:  Glycoconjugate Benzene Sulfonamides Prepared by “Click-Tailing”

  摘要：

  Aryl and heteroaryl sulfonamides (ArSO2NH2) are therapeutically used to inhibit the catalytic activity of carbonic anhydrases (CAs). Using a "click- tail" approach a novel class of glycoconjugate benzene sulfonamides have been synthesized that contain diverse carbohydrate- triazole tails. These compounds were assessed for their ability to inhibit three human CA isozymes in vitro: cytosolic hCA I and hCA II and transmembrane, tumor- associated hCA IX. This isozyme has a minimal expression in normal tissue but is overexpressed in hypoxic tumors and its inhibition is a current approach toward new cancer therapies. The qualitative structure- activity for all derivatives demonstrated that the stereochemical diversity present within the carbohydrate tails effectively interrogated the CA active site topology, to generate several inhibitors that were potent and selective toward hCA IX, an important outcome in the quest for potential cancer therapy applications based on CA inhibition.

  DOI：

  10.1021/jm060967z

文献信息

• A Novel Class of Carbonic Anhydrase Inhibitors:  Glycoconjugate Benzene Sulfonamides Prepared by “Click-Tailing”
  作者：Brendan L. Wilkinson、Laurent F. Bornaghi、Todd A. Houston、Alessio Innocenti、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm060967z

  日期：2006.11.1

  Aryl and heteroaryl sulfonamides (ArSO2NH2) are therapeutically used to inhibit the catalytic activity of carbonic anhydrases (CAs). Using a "click- tail" approach a novel class of glycoconjugate benzene sulfonamides have been synthesized that contain diverse carbohydrate- triazole tails. These compounds were assessed for their ability to inhibit three human CA isozymes in vitro: cytosolic hCA I and hCA II and transmembrane, tumor- associated hCA IX. This isozyme has a minimal expression in normal tissue but is overexpressed in hypoxic tumors and its inhibition is a current approach toward new cancer therapies. The qualitative structure- activity for all derivatives demonstrated that the stereochemical diversity present within the carbohydrate tails effectively interrogated the CA active site topology, to generate several inhibitors that were potent and selective toward hCA IX, an important outcome in the quest for potential cancer therapy applications based on CA inhibition.