2,2',3,3',4',6,6'-hepta-O-acetyl-S-(prop-2-ynyl)-1-thio-β-maltoside | 1333497-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2',3,3',4',6,6'-hepta-O-acetyl-S-(prop-2-ynyl)-1-thio-β-maltoside
• 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-prop-2-ynylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1333497-84-9
• 化学式: C₂₉H₃₈O₁₇S
• 分子量: 690.677
• InChiKey: PXLGAZGHFVYUJV-OXUWYBOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2,2',3,3',4',6,6'-hepta-O-acetyl-S-(prop-2-ynyl)-1-thio-β-maltoside 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 sodium methylate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 p-(4-{[β-maltosyl]sulfonylmethyl}-5-iodo-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：

  3-溴丙炔 、 β-D-麦芽糖八乙酸酯 在 三氟化硼乙醚 、 硫脲 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以37%的产率得到2,2',3,3',4',6,6'-hepta-O-acetyl-S-(prop-2-ynyl)-1-thio-β-maltoside
  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