p-(4-{[2',2'',3',3',4',6',6''-hepta-O-acetyl-β-maltosyl]thiomethyl}-1H-1,2,3-triazol-1-yl)benzenesulfonamide | 1333497-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-(4-{[2',2'',3',3',4',6',6''-hepta-O-acetyl-β-maltosyl]thiomethyl}-1H-1,2,3-triazol-1-yl)benzenesulfonamide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[[1-(4-sulfamoylphenyl)triazol-4-yl]methylsulfanyl]oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1333497-88-3
• 化学式: C₃₅H₄₄N₄O₁₉S₂
• 分子量: 888.882
• InChiKey: WHBDHHIQZXIDLZ-ATUSIUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  60
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  336
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  p-(4-{[2',2'',3',3',4',6',6''-hepta-O-acetyl-β-maltosyl]thiomethyl}-1H-1,2,3-triazol-1-yl)benzenesulfonamide 在 甲醇 、 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 p-(4-{[β-maltosyl]sulfonylmethyl}-1H-1,2,3-triazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Targeting Hypoxic Tumor Cell Viability with Carbohydrate-Based Carbonic Anhydrase IX and XII Inhibitors

  摘要：

  Carbonic anhydrase (CA) enzymes, specifically membrane-bound isozymes CA IX and CA XII, underpin a pH-regulating system that enables hypoxic tumor cell survival and proliferation. CA IX and XII are implicated as potential targets for the development of new hypoxic cancer therapies. To date, only a few small molecules have been characterized in CA-relevant cell and animal model systems. In this paper, we describe the development of a new class of carbohydrate-based small molecule CA inhibitors, many of which inhibit CA IX and XII within a narrow range of low nanomolar K-i values (5.3-11.2 nM). We evaluate for the first time carbohydrate-based CA inhibitors in cell-based models that emulate the protective role of CA IX in an acidic tumor microenvironment. Our findings identified two inhibitors (compounds 5 and 17) that block CA IX-induced survival and have potential for development as in vivo cancer cell selective inhibitors.

  DOI：

  10.1021/jm200892s
• 作为产物：
  描述：

  磺胺 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 亚硝酸特丁酯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 p-(4-{[2',2'',3',3',4',6',6''-hepta-O-acetyl-β-maltosyl]thiomethyl}-1H-1,2,3-triazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Targeting Hypoxic Tumor Cell Viability with Carbohydrate-Based Carbonic Anhydrase IX and XII Inhibitors

  摘要：

  Carbonic anhydrase (CA) enzymes, specifically membrane-bound isozymes CA IX and CA XII, underpin a pH-regulating system that enables hypoxic tumor cell survival and proliferation. CA IX and XII are implicated as potential targets for the development of new hypoxic cancer therapies. To date, only a few small molecules have been characterized in CA-relevant cell and animal model systems. In this paper, we describe the development of a new class of carbohydrate-based small molecule CA inhibitors, many of which inhibit CA IX and XII within a narrow range of low nanomolar K-i values (5.3-11.2 nM). We evaluate for the first time carbohydrate-based CA inhibitors in cell-based models that emulate the protective role of CA IX in an acidic tumor microenvironment. Our findings identified two inhibitors (compounds 5 and 17) that block CA IX-induced survival and have potential for development as in vivo cancer cell selective inhibitors.

  DOI：

  10.1021/jm200892s