4-(4-{(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide | 935678-24-3

• 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-{(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl]methoxy}oxan-2-yl]methyl acetate；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[1-(4-sulfamoylphenyl)triazol-4-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 935678-24-3
• 化学式: C₂₃H₂₈N₄O₁₂S
• 分子量: 584.561
• InChiKey: QGAJDSWCAJPCOD-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  223
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4-(4-{(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide 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-{(β-D-glucopyranosyl)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
• 作为产物：
  描述：

  4-azidobenzenesulfonamide 、 2-炔丙基-四-O-乙酰基-β-D-吡喃葡萄糖苷 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 叔丁醇 为溶剂， 以77%的产率得到4-(4-{(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)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

文献信息

• Carbonic Anhydrase Inhibitors:  Inhibition of Isozymes I, II, and IX with Triazole-Linked <i>O</i>-Glycosides of Benzene Sulfonamides
  作者：Brendan L. Wilkinson、Laurent F. Bornaghi、Todd A. Houston、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm061320h

  日期：2007.4.1

  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.